LPC09122 CHEMISTRY II                                                     COURSE AGENDAMODULE 1. HYDROCARBONS IN LIFE     ...
MODULE 1                                              TOPIC EXPLANATION 1. ORGANIC CHEMISTRY1.1 Nature and its Chemical Re...
Nitrogen is an element needed to from proteins, which                                                                     ...
T      H E             E      A R T H                      C       H A R T E RP R E A M B L EWe stand at a critical moment...
T H E      E A RT H C H AR T ERd. Internalize the full environmental and social costs of goods and services in the selling...
T H E         E A RT H C H AR T ERand redress for environmental harm and the threat of such harm.e. Eliminate corruption i...
TOPIC EXPLANATION 2. CARBON2.1 Chemical and physical properties of carbonCarbon is a non-metal element, its symbol is C an...
Orbital                       Description                                                    Image               This orbi...
Parent chain             Principal hydrocarbon chain formed by the chain containing the                                   ...
When it is connected to the third carbon.                           Tert-butylExample:                       Compound     ...
3.5 Importance in lifeEvery hydrocarbon reacts with oxygen, producing carbon dioxide (CO2) and water (H2O), being its main...
the groups are named in alphabetical order and finally the main structure: benzene or toluene. If you have more than two e...
 Trinitrotoluene: The 2,4,6-trinitrotoluene is a solid chemical compound with a yellow-colored surface. The main entries ...
Module 2.                                                       TOPIC EXPLANATION 5. ALCOHOLS5.1 Alcohol NomenclatureAlcoh...
For cyclic hydrocarbons                                            Example:You just need to add the suffix –ol. For compou...
TOPIC EXPLANATION 6. ALDEHYDES Aldehydes are compounds containing oxygen molecules in their formula. The carbon is always ...
The carbonyl group is strongly active, and takes part in many reactions. A common reaction in aldehydes is when the bond b...
7.2 PropertiesKetones contain the carbonyl group in the secondary carbons, reason why the carbon is not united to a hydrog...
Module 3. Carboxylic acids, esters, ethers, amines, amides                                              TOPIC EXPLANATION ...
8.2 PropertiesAs alcohols, aldehydes and ketones studied in the previous module, for the acid radical of carboxylic acids,...
Ether is symmetric when to each side of the oxygen you have the same alkyl or aryl group. This type of ether is produced b...
9.4 AmidesAmides are derivatives of carboxylic acids, where the –OH group is replaced by a NH2.                           ...
Although plastics are a big source of contamination, it is important to know that this isdue to a lack of a recycling cult...
Module 4. Petroleum, biomolecules and combustion and fermentation reactions                                              T...
A well balanced diet will give you the opportunity to maintain a healthy body; when thefood intake is poor, we lose the po...
11.3 EsterificationThe esterification is, as we studied before, the formation of esters. This reaction is considered impor...
Chemistry ii (topic explainations)(1)
Chemistry ii (topic explainations)(1)
Chemistry ii (topic explainations)(1)
Chemistry ii (topic explainations)(1)
Chemistry ii (topic explainations)(1)
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Chemistry ii (topic explainations)(1)

  1. 1. LPC09122 CHEMISTRY II COURSE AGENDAMODULE 1. HYDROCARBONS IN LIFE MODULE 4. PETROLEUM, BIOMOLECULES AND COMBUSTION  Topic 1. Organic Chemistry AND FERMENTATION REACTIONS 1.1Nature and its chemicals reactions  Topic 11. Chemical Reactions II 1.2Definition of organic chemistry 11.1Combustion 1.3Organic Chemistry 11.2Fermentation  Topic 2. Carbon 11.3Esterification 2.1Chemical and physical properties of carbon 11.4Uses 2.2Hybridization  Topic 12. Petroleum 2.3 Sigma () and Pi ()bond 12.1Derivatives  Topic 3. Hydrocarbons 12.2Petroleum Refinery 3.1Alkanes 12.3Importance 3.2Alkenes  Topic 13. Biomolecules 3.3Alkynes 13.1Principal Types of Biomolecules 3.4Cyclic Hydrocarbons 13.2Functional groups 3.5Importance in life 13.3Biomolecules groupsMODULE 2. ALCOHOLS, ALDEHYDES, AND KETONES 13.4Importance in health  Topic 5. Alcohols 5.1Classification 5.2Nomenclature 5.3Properties and importance  Topic 6. Aldehydes 6.1Nomenclature 6.2Properties 6.3Importance  Topic 7. Ketones 7.1Nomenclature 7.2Properties 7.3ImportanceMODULE 3. CARBOXYLIC ACIDS, ESTERS, ETHERS, AMINES,AMIDES TOPIC  8. Carboxylic acids 8.1Nomenclature 8.2Properties 8.3Importance  Topic 9. Functional Groups 9.1 Esters 9.2Ethers 9.3Amines 9.4Amides 9.5 Properties and importance  Topic 10. Chemical Reactions I 10.1Polymerization 10.2SaponificationBibliography  McMurry, J. (2008). Organic Chemistry (7th Ed). USA: Thomson. (ISBN: 9780495112587) 1
  2. 2. MODULE 1 TOPIC EXPLANATION 1. ORGANIC CHEMISTRY1.1 Nature and its Chemical Reactions The Earth is a planet that shares its origin with other planets that all together orbit around a big star called Sun. If we compare the Earth with other planets of the solar system, we can establish that it is small, has high density which is 5.52 g/cm3, its temperature is 22°C, which allows maintaining water in its liquid phase in big quantities, covering a 70% of its surface and allowing the existence of life. Many changes have taken place in the history of planet Earth. Some of them are natural consequences of Earth’s physical and chemical properties, but others are related to the roll of man, who has been able to change the environment in order to satisfy his necessities and commodities.In the twenty first century we have realized that we still live in a small planet, which orbits around the sun, and that we wish to maintainit healthy for the maximum amount of time. This is why we need to know the chemical elements that form the planet, so we can takecare of the reactions between them, and favor them to life. A compound not studied in organic chemistry is Water. Water is vital for man’s life, since 75% of the human body is water. To maintain us alive we drink water from rivers, lakes and from underground. In nature, water is constantly recycled by a cycle, which you can view in figure 1. Unfortunately man has modified this cycle with his actions, adding residual water in rivers, spilling petroleum in the sea and not allowing the filtration trough the soil due to roads and expansion of cities. The carbon cycle is a nature process which transforms carbon dioxide into oxygen, and is indeed necessary for human life. Photosynthesis is developed primordially in plants, since they emit oxygen into the environment, but Figure 1. The water cycle deforestation and the excessive use of http://www.explora.cl/otros/agua/ciclo2.html. hydrocarbons as a source of energy are affecting Reproduced for educational purposes. significatively this process. Figure 2. The carbon cycle http://www.windows.ucar.edu/tour/link=/earth/Life/biogeochem.html&edu=high&fr=t%20t Reproduced for educational purposes 2
  3. 3. Nitrogen is an element needed to from proteins, which are the base of fertilizers used in agriculture, and can be obtained in artificial ways. The excessive use or high concentrations of nitrogen in soil is considered to be a pollutant, due to water erosion. Figure 3. The nitrogen cycle http://www.physicalgeography.net/fundamentals/9s.ht ml Reproduced for educational purposes.1.2 Definition of Organic ChemistryOrganic chemistry is a discipline within chemistry that studies the composition of substances and its changes, focusing in organiccompounds; it was considered in the past that it was only present in living organisms, but with time it has been synthesized also in inertsubstances which contain carbon as its base element.1.3 Organic ChemistryIn this course you will learn that the gas you use in the stove is a hydrocarbon, the alcohol you use with medical purposes, is also ahydrocarbon. Other types of hydrocarbons are: aldehydes, ketone, carboxylic acids, esters, ethers, amines, amides, and bio-molecules,which are part of daily use products. These hydrocarbons are obtained from vegetables and animals, and their molecules are formed bycarbon, hydrogen, oxygen and nitrogen.The knowledge of the characteristics of these compounds will allow us to have the basesto assure Earth’s Sustainability. We will be searching for a balance in having humancomfort without damaging the environment and its natural resources, which are the baseof life. }Knowing these compounds will also help us understand our responsibility incontamination. We must analyze this in The Earth Charter which declares theresponsibility of humans to life and to future generations. 3
  4. 4. T H E E A R T H C H A R T E RP R E A M B L EWe stand at a critical moment in Earths history, a time when humanity must choose its future. As the worldbecomes increasingly interdependent and fragile, the future at once holds great peril and great promise. To moveforward we must recognize that in the midst of a magnificent diversity of cultures and life forms we are one humanfamily and one Earth community with a common destiny. We must join together to bring forth a sustainable globalsociety founded on respect for nature, universal human rights, economic justice, and a culture of peace. Towardsthis end, it is imperative that we, the peoples of Earth, declare our responsibility to one another, to the greatercommunity of life, and to future generations. Earth, Our Home Humanity is part of a vast evolving universe. Earth, our home, is alive with a unique community of life. The forces of nature make existence a demanding and uncertain adventure, but Earth has provided the conditions essential to lifes evolution. The resilience of the community of life and the well-being of humanity depend upon preserving a healthy biosphere with all its ecological systems, a rich variety of plants and animals, fertile soils, pure waters, and clean air. The global environment with its finite resources is a common concern of all peoples. The protection of Earths vitality, diversity, and beauty is a sacred trust. The Global Situation The dominant patterns of production and consumption are causing environmental devastation, the depletion of resources, and a massive extinction of species. Communities are being undermined. The benefits of development are not shared equitably and the gap between rich and poor is widening. Injustice, poverty, ignorance, and violent conflict are widespread and the cause of great suffering. An unprecedented rise in human population has overburdened ecological and social systems. The foundations of global security are threatened. These trends are perilous—but not inevitable. The Challenges Ahead The choice is ours: form a global partnership to care for Earth and one another or risk the destruction of ourselves and the diversity of life. Fundamental changes are needed in our values, institutions, and ways of living. We must realize that when basic needs have been met, human development is primarily about being more, not having more. We have the knowledge and technology to provide for all and to reduce our impacts on the environment. The emergence of a global civil society is creating new opportunities to build a democratic and humane world. Our environmental, economic, political, social, and spiritual challenges are interconnected, and together we can forge inclusive solutions. Universal Responsibility To realize these aspirations, we must decide to live with a sense of universal responsibility, identifying ourselves with the whole Earth community as well as our local communities. We are at once citizens of different nations and of one world in which the local and global are linked. Everyone shares responsibility for the present and future well-being of the human family and the larger living world. The spirit of human solidarity and kinship with all life is strengthened when we live with reverence for the mystery of being, gratitude for the gift of life, and humility regarding the human place in nature.We urgently need a shared vision of basic values to provide an ethical foundation for the emerging worldcommunity. Therefore, together in hope we affirm the following interdependent principles for a sustainable way oflife as a common standard by which the conduct of all individuals, organizations, businesses, governments, andtransnational institutions is to be guided and assessed.
  5. 5. T H E E A RT H C H AR T ERP R I N C I P L E SI. RESPEC T AND CARE F OR THE COMMU NITY O F LIFE1. Respect Earth and life in all its diversity.a. Recognize that all beings are interdependent and every form of life has value regardless of its worth to humanbeings.b. Affirm faith in the inherent dignity of all human beings and in the intellectual, artistic, ethical, and spiritualpotential of humanity.2. Care for the community of life with understanding, compassion, and love.a. Accept that with the right to own, manage, and use natural resources comes the duty to prevent environmentalharm and to protect the rights of people.b. Affirm that with increased freedom, knowledge, and power comes increased responsibility to promote thecommon good.3. Build democratic societies that are just, participatory, sustainable, and peaceful.a. Ensure that communities at all levels guarantee human rights and fundamental freedoms and provide everyonean opportunity to realize his or her full potential.b. Promote social and economic justice, enabling all to achieve a secure and meaningful livelihood that isecologically responsible.4. Secure Earths bounty and beauty for present and future generations.a. Recognize that the freedom of action of each generation is qualified by the needs of future generations.b. Transmit to future generations values, traditions, and institutions that support the long-term flourishing ofEarths human and ecological communities. In order to fulfill these four broad commitments, it is necessary to:I I . E C O L O GI C A L I N T E GR I T Y5. Protect and restore the integrity of Earths ecological systems, with special concern forbiological diversity and the natural processes that sustain life.a. Adopt at all levels sustainable development plans and regulations that make environmental conservation andrehabilitation integral to all development initiatives.b. Establish and safeguard viable nature and biosphere reserves, including wild lands and marine areas, to protectEarths life support systems, maintain biodiversity, and preserve our natural heritage.c. Promote the recovery of endangered species and ecosystems.d. Control and eradicate non-native or genetically modified organisms harmful to native species and theenvironment, and prevent introduction of such harmful organisms.e. Manage the use of renewable resources such as water, soil, forest products, and marine life in ways that do notexceed rates of regeneration and that protect the health of ecosystems.f. Manage the extraction and use of non-renewable resources such as minerals and fossil fuels in ways thatminimize depletion and cause no serious environmental damage.6. Prevent harm as the best method of environmental protection and, when knowledge is limited,apply a precautionary approach.a. Take action to avoid the possibility of serious or irreversible environmental harm even when scientific knowledgeis incomplete or inconclusive.b. Place the burden of proof on those who argue that a proposed activity will not cause significant harm, and makethe responsible parties liable for environmental harm.c. Ensure that decision making addresses the cumulative, long-term, indirect, long distance, and globalconsequences of human activities.d. Prevent pollution of any part of the environment and allow no build-up of radioactive, toxic, or other hazardoussubstances.e. Avoid military activities damaging to the environment.7. Adopt patterns of production, consumption, and reproduction that safeguard Earthsregenerative capacities, human rights, and community well-being.a. Reduce, reuse, and recycle the materials used in production and consumption systems, and ensure that residualwaste can be assimilated by ecological systems.b. Act with restraint and efficiency when using energy, and rely increasingly on renewable energy sources such assolar and wind.c. Promote the development, adoption, and equitable transfer of environmentally sound technologies. -2-
  6. 6. T H E E A RT H C H AR T ERd. Internalize the full environmental and social costs of goods and services in the selling price, and enableconsumers to identify products that meet the highest social and environmental standards.e. Ensure universal access to health care that fosters reproductive health and responsible reproduction.f. Adopt lifestyles that emphasize the quality of life and material sufficiency in a finite world.8. Advance the study of ecological sustainability and promote the open exchange and wideapplication of the knowledge acquired.a. Support international scientific and technical cooperation on sustainability, with special attention to the needs ofdeveloping nations.b. Recognize and preserve the traditional knowledge and spiritual wisdom in all cultures that contribute toenvironmental protection and human well-being.c. Ensure that information of vital importance to human health and environmental protection, including geneticinformation, remains available in the public domain.III . SOCI AL AND ECONO MIC JU STICE9. Eradicate poverty as an ethical, social, and environmental imperative.a. Guarantee the right to potable water, clean air, food security, uncontaminated soil, shelter, and safe sanitation,allocating the national and international resources required.b. Empower every human being with the education and resources to secure a sustainable livelihood, and providesocial security and safety nets for those who are unable to support themselves.c. Recognize the ignored, protect the vulnerable, serve those who suffer, and enable them to develop theircapacities and to pursue their aspirations.10. Ensure that economic activities and institutions at all levels promote human development inan equitable and sustainable manner.a. Promote the equitable distribution of wealth within nations and among nations.b. Enhance the intellectual, financial, technical, and social resources of developing nations, and relieve them ofonerous international debt.c. Ensure that all trade supports sustainable resource use, environmental protection, and progressive laborstandards.d. Require multinational corporations and international financial organizations to act transparently in the publicgood, and hold them accountable for the consequences of their activities.11. Affirm gender equality and equity as prerequisites to sustainable development and ensureuniversal access to education, health care, and economic opportunity.a. Secure the human rights of women and girls and end all violence against them.b. Promote the active participation of women in all aspects of economic, political, civil, social, and cultural life asfull and equal partners, decision makers, leaders, and beneficiaries.c. Strengthen families and ensure the safety and loving nurture of all family members.12. Uphold the right of all, without discrimination, to a natural and social environmentsupportive of human dignity, bodily health, and spiritual well-being, with special attention to therights of indigenous peoples and minorities.a. Eliminate discrimination in all its forms, such as that based on race, color, sex, sexual orientation, religion,language, and national, ethnic or social origin.b. Affirm the right of indigenous peoples to their spirituality, knowledge, lands and resources and to their relatedpractice of sustainable livelihoods.c. Honor and support the young people of our communities, enabling them to fulfill their essential role in creatingsustainable societies.d. Protect and restore outstanding places of cultural and spiritual significance.I V . D E M O C R A C Y, N O N V I O L E N C E , A N D P E A C E13. Strengthen democratic institutions at all levels, and provide transparency and accountabilityin governance, inclusive participation in decision making, and access to justice.a. Uphold the right of everyone to receive clear and timely information on environmental matters and alldevelopment plans and activities which are likely to affect them or in which they have an interest.b. Support local, regional and global civil society, and promote the meaningful participation of all interestedindividuals and organizations in decision making.c. Protect the rights to freedom of opinion, expression, peaceful assembly, association, and dissent.d. Institute effective and efficient access to administrative and independent judicial procedures, including remedies -3-
  7. 7. T H E E A RT H C H AR T ERand redress for environmental harm and the threat of such harm.e. Eliminate corruption in all public and private institutions.f. Strengthen local communities, enabling them to care for their environments, and assign environmentalresponsibilities to the levels of government where they can be carried out most effectively.14. Integrate into formal education and life-long learning the knowledge, values, and skillsneeded for a sustainable way of life.a. Provide all, especially children and youth, with educational opportunities that empower them to contributeactively to sustainable development.b. Promote the contribution of the arts and humanities as well as the sciences in sustainability education.c. Enhance the role of the mass media in raising awareness of ecological and social challenges.d. Recognize the importance of moral and spiritual education for sustainable living.15. Treat all living beings with respect and consideration.a. Prevent cruelty to animals kept in human societies and protect them from suffering.b. Protect wild animals from methods of hunting, trapping, and fishing that cause extreme, prolonged, or avoidablesuffering.c. Avoid or eliminate to the full extent possible the taking or destruction of non-targeted species.16. Promote a culture of tolerance, nonviolence, and peace.a. Encourage and support mutual understanding, solidarity, and cooperation among all peoples and within andamong nations.b. Implement comprehensive strategies to prevent violent conflict and use collaborative problem solving to manageand resolve environmental conflicts and other disputes.c. Demilitarize national security systems to the level of a non-provocative defense posture, and convert militaryresources to peaceful purposes, including ecological restoration.d. Eliminate nuclear, biological, and toxic weapons and other weapons of mass destruction.e. Ensure that the use of orbital and outer space supports environmental protection and peace.f. Recognize that peace is the wholeness created by right relationships with oneself, other persons, other cultures,other life, Earth, and the larger whole of which all are a part.T H E W A Y F O R W A R DAs never before in history, common destiny beckons us to seek a new beginning. Such renewal is the promise ofthese Earth Charter principles. To fulfill this promise, we must commit ourselves to adopt and promote the valuesand objectives of the Charter.This requires a change of mind and heart. It requires a new sense of global interdependence and universalresponsibility. We must imaginatively develop and apply the vision of a sustainable way of life locally, nationally,regionally, and globally. Our cultural diversity is a precious heritage and different cultures will find their owndistinctive ways to realize the vision. We must deepen and expand the global dialogue that generated the EarthCharter, for we have much to learn from the ongoing collaborative search for truth and wisdom.Life often involves tensions between important values. This can mean difficult choices. However, we must findways to harmonize diversity with unity, the exercise of freedom with the common good, short-term objectives withlong-term goals. Every individual, family, organization, and community has a vital role to play. The arts, sciences,religions, educational institutions, media, businesses, nongovernmental organizations, and governments are allcalled to offer creative leadership. The partnership of government, civil society, and business is essential foreffective governance.In order to build a sustainable global community, the nations of the world must renew their commitment to theUnited Nations, fulfill their obligations under existing international agreements, and support the implementation ofEarth Charter principles with an international legally binding instrument on environment and development.Let ours be a time remembered for the awakening of a new reverence for life, the firm resolve to achievesustainability, the quickening of the struggle for justice and peace, and the joyful celebration of life.O R I G I N O F T H E E A R T H C H A R T E RThe Earth Charter was created by the independent Earth Charter Commission, which was convened as a follow-up to the 1992 Earth Summit in orderto produce a global consensus statement of values and principles for a sustainable future. The document was developed over nearly a decade through anextensive process of international consultation, to which over five thousand people contributed. The Charter has been formally endorsed by thousands oforganizations, including UNESCO and the IUCN (World Conservation Union). For more information, please visit www.EarthCharter.org. -4-
  8. 8. TOPIC EXPLANATION 2. CARBON2.1 Chemical and physical properties of carbonCarbon is a non-metal element, its symbol is C and it is the first member of the fourth group in the periodic table. Its basic inorganiccompounds are: CO and CO2 when this last reacts with strong base aqueous solutions it forms carbonic acid salts, also known ascarbonates.Chemical properties: Property Value Definition Atomic number Z=6 Number of protons or electrons in an atom. Oxidation states 2, 4 Electrons that can be combined to form a bond. 2 2 2 Electronic configuration 1s 2s 2p Distribution of the atom’s electrons. Atomic mass 12.01 uma The atom’s mass. Electro negativity 2.55 Ability of an atom to attract electrons toward itself in a covalent bond. -12 Atomic radius 77 x 10 m Measure of the size of its atoms. Ionic radius 16 pm Measure of the size of an ion in a crystal structure. Electron affinity 1.26 eV Amount of energy required to form an anion. Ionization energy 11.26 eV Amount of energy required to form a cation.Physical properties:Carbon can be present in different physical forms, phenomena called allotropy. You can find it in a crystal form (diamond and graphite)or amorphous, which means without a form (soft coal and anthracite, among others); its physical characteristics depends of the form itis presented. State Characteristics Form 3 Diamond The hardest of the natural minerals; its density is 3.5 g/cm . Each atom is found in the center of a tetrahedron united to four carbons which forms its vertexes. Graphite It has a laminar structure, in which each carbon atom is united to another, forming on a hexagonal system with three cyclical structures; its plates are separated to form a dry lubricant, which allows them to slide one over the other. Soft coal Great calorific potential. Amorphous Anthracite It burns with a short and blue flame. Amorphous2.2 Orbital HybridizationThe orbital is the region or space in an atom where the electron is located. There are different forms and types. Its type indicates theamount of energy an electron has, and the atom arrangement can determine its chemical behavior. The orbital are clouds that resemblethe movement of electrons, its density depends on the probability of electrons existing in that zone. The carbon atom has six electrons;it has the first orbital complete 1s, and has two electrons in orbital 2s, and the remaining two electrons, one is found in 2px and theother in 2py. 4
  9. 9. Orbital Description Image This orbital, named 1s, has the lowest energy level. Its shape is a sphere, its highest density is 1s located in the outskirts and the probability of finding an electron in this area is of 95%. This orbital is bigger in size than 1s It is a sphere 2s in which the center is the origin of the X, Y and Z coordinates. This orbital consist of two ellipsoids where the atom’s nucleus is located. We find this orbital 2p oriented on the X, Y or Z axis, as you can see them in the following drawings.Hybridization is the concept of mixing atomic orbitals in order to produce a new orbital with different functions.There are different hybrids that are formed in different orbital, with the aim of forming a better chemical bond. In the case of organicchemistry, Carbon always uses its fourth valence; in order to achieve this, hybridization exists in the 2s and 2p orbitals, by which the fourelectrons that originally where found there are now rearranged in 1s, 2px, 2py and 2pz orbitals, forming the SP3 hybrid. When theelectrons don’t reach to pair on the Pz orbital, the SP2 hybrid is formed, and finally if the S and Px orbital are involved, the SP hybrid isformed. Involved Orbitals Hybrid Figure Form S y Px SP 2 S, Px y Py SP 3 S, Px, Py y Pz SP2.3 Sigma (s) and Pi (p) BondA chemical bond is the union between two atoms of the same or different element. You can classify them by its ionic bond, which isformed from a complete transfer of electrons from one atom to the other, or by covalent bonds, which is when atoms share theirelectrons. The last one is the one most frequently present in organic compounds.One way of explaining these bonds is by the configuration of the atomic orbital described above (s,p), but they can also be explained byvisualizing the molecule as a hole, using molecular orbitals which are named sigma (s) and pi (p). The sigma (s) bond is a covalent bondin which the electronic density between its two nucleuses is high, and it is symmetric around the axis that connects these two nucleuses.The pi (p) bond is also a covalent bond, but its electronic density is concentrated in two regions, above and underneath the axis thatconnects the two nucleuses. Bond Electronic density Form In Hydrocarbons Sigma (s) Symmetric around the axis. Simple bonds. Pi (p) Asymmetric in two regions, above and underneath the axis. Double or triple bonds. 3In hydrocarbon bonds, when four simple SP bonds are formed around the carbon the sigma bond is formed, but when the carbon has a 2double bond with another carbon the SP hybrid is formed, setting free the 2pz; in this two carbons the pi () bond is formed. Finally thetriple hybrid bond is the SP setting free for the pi () bond the Py and Pz.When carbon bonds with another carbon, it has the characteristic of forming chains which can be from two until big numbers. This canbe classified as: 5
  10. 10. Parent chain Principal hydrocarbon chain formed by the chain containing the maximum number of carbons. Linear chain or side- Occurs where an open line of carbons is formed. chain Branched chain When one or more carbons of the parent chain are bond with smaller chains called radicals. Closed chains When the last carbon is united with the first carbon, closing the chain.The carbons in these chains can be classified according to whom they are united. Primary carbon bond has one carbon neighbor,secondary carbon bond has two carbon neighbors, tertiary carbon bond has three carbon neighbors, and quaternary carbon bond hasfour carbon neighbors. TOPIC EXPLANATION 3. HYDROCARBONS3.1 AlkanesAlkanes are hydrocarbons with open chain, in which the links between carbon and carbon are single bonds. Its general formula is CnH2n+2and they can be in straight-chain or can have branches. When a compound has the same number of carbons and hydrogens but thestructure of its chain is different this compound is called structural isomer.If we have 8 C, and based on the alkane general formula, we must have 18H, how many ways can you arrange these elements withoutforgetting that each carbon must have 4 bonds and each hydrogen only one? The ways in which you arrange these structures areisomers of this compound, always considering every possible combination. Formula Name Molecular formula Condensed formula Structural formula Ethane C2 H6 CH3-CH3When a compound has branches, it is necessary to take into consideration which is the longest continuous chain formed by carbons, theparent chain, and then we have to number the carbon atoms starting from the nearest branch. After doing this, you name the numbersof carbon atoms where the side-chain is located; if there is more than one side-chain of the same type, use the prefix –di (2), -tri (3), -tetra (4),etc., before it. You have to take into consideration that you name them in alphabetical order, and at the end you will add theparent-chain suffix –ane. Below is a table listing the most common radicals and an example of nomenclature of alkanes: Alkane Formula Radical Methane Just one Carbon Methyl Ethane An H is lost, doesn’t matter in which C. Ethyl If the H is lost in one end of the chain. Propyl Propane If the H is lost in the second C. Isopropyl When it is bond in the fourth carbon. Butyl When it is connected to the second Sec-butyl Butane carbon. Comes from the butane isomer. Isobutyl 6
  11. 11. When it is connected to the third carbon. Tert-butylExample: Compound Explanation Name 5,6-diethyl-2-methyloctane3.2 AlkenesAlkenes are hydrocarbons that have double bonds between carbons (C=C). Its general formula is CnH2n.To determine its nomenclature, like alkanes, you have to search for the parent chain, the longest carbon chain that contains the doublebond. Number the carbons starting where the nearest double bond is located. Name the radicals in alphabetical order, putting beforethem the carbon number in which they are located, then the number where the double bond is located and finally write the name of theparent chain with the suffix –ene. If there is more than one double bond, you add the prefix di-, tri-, etc., before the name. If thedouble bond is located in different carbons, you have a position isomerism. Example: Chain Explanation Name 3,4-diethyl-7 methyl-1,6-octadiene.3.3 AlkynesAlkynes are hydrocarbons that have a triple bond between carbons (C≡C),when they have only one triple bond its general formula is CnH2n-2.Like alkanes and alkenes, to set the nomenclature of alkynes you searchfor the parent chain, which contains the triple bond. You number thecarbons starting where the triple bond is nearest. You have to name theradicals in alphabetical order, putting before them the number of thecarbon in which they are located, then the number where the triple bondis located and finally write the name of the parent chain with the suffix –yne. If there is more than one triple bond, add the prefix di-, tri-, etc.,before the name. An example can be:3.4 Cyclic HydrocarbonsThese hydrocarbons are named cyclic, because its carbons are united forming a closed figure. You name them with the cyclic prefix tothe name to which it corresponds: alkane if it has a single bond, alkene if it has a double bond or alkyne if there is a triple bond.In many occasions a geometric figure is used to indicate them. The smallest is the cyclopropane, forming a triangle and beyond you go innaming them. 7
  12. 12. 3.5 Importance in lifeEvery hydrocarbon reacts with oxygen, producing carbon dioxide (CO2) and water (H2O), being its main use in daily life as fuel.The vegetal organic matter, when fermented in anaerobic conditions, forms methane, and during many years it was burned withoutusing it. Nowadays it is known for its potential energy; other alkanes that share this characteristic of being an energy source are thepropane and butane, which are used in stoves at homes and industries.The mixture of hydrocarbons with between five or ten carbons produces the famous octanes, which we call gasoline. But this is not itsonly use, some alkanes, like cyclohexane, are used in the production of nylon, and the hexane is necessary for oil extractions such as soy,peanut or cotton.The alkenes are the raw materials for plastics such as the polyethylene, Teflon, polyvinyl chloride which has many uses in our daily life.The alkynes are materials for the preparation of agricultural products, pharmaceutics, and are also used as fuels, because they producea hot flame which is required in welding processes.Now you can imagine a life without gasoline, a stove without gas. Imagine if all the plastic materials or nylons were missing...Do you consider that hydrocarbons are important for your daily life? TOPIC EXPLANATION 4. AROMATIC HYDROCARBONS4.1 BenzeneThe Benzene is a liquid with a characteristic odor; it is the basic compound of the aromatic family. Its molecular formula is C6H6, andevery carbon has three covalent bonds, one double bond, and two single bonds. Its structure can produce resonance giving the benzenegreat stability. You can represent the compound with a regular hexagon with alternate double bonds, or in a simple way you canrepresent it as a hexagonal with an interior circle.4.2 NomenclatureSome compounds are formed by the union of several benzene rings, Naphthalene is among the most important and its structure isformed by two fused benzene rings. Benzo(alpha)pyrene is another important structure formed by 5 rings, which consists of benzenerings fused to a pyrene molecule.Those which are benzene derivatives have daily use common names, but you can also name them according to IUPAC. If you have asubstituting group in which the carbon is the same compound, it will be named by using the word benzene first. When there are twosubstituting groups you may end up with three different isomers; Ortho Meta Para If they are in two contiguous carbons, for When two carbons are apart, for When there is a substitution in the example number 1 and 2, you can use the example in the carbon 1 and 3, you can carbon 1 and 4, to name it you use the prefix ortho-, that can be abbreviated by o- use the prefix meta-, abbreviated by m- prefix para-, that can be abbreviated before the word benzene. before the word benzene. by p-, before the word benzene.Methylbenzene is also known as toluene, and many other compounds are named based on it. For example you can consider the methylcarbon as one, and use the prefixes orto-, meta- and para- when you have a substitute.Those compounds that have three or more substitutes will be numbered in a direction that allows them to have the smallest numbers intotal carbons. If the principal structure is a toluene, the methyl will always be one, and in the name the number of carbons is written, 8
  13. 13. the groups are named in alphabetical order and finally the main structure: benzene or toluene. If you have more than two equal groupsin your ring, you will use the prefixes di-, tri-, etc., to name these groups. Toluene O-nitrotoluene 2-methyl-3-nitrotolueno4.3 Physical propertiesThe aromatic compounds receive this name because the majority of them have a peculiar or characteristic odor. Many of thesecompounds are toxic and carcinogen, reason why they are considered big pollutants, and also have the facility to introduce themselvesinto biological membranes and mess with them, causing severe health problems.Among them, they have similar characteristics, but their differences can allow them to be used in many ways. Some of them areinsoluble to water, and some are mayor solutes in organic solvents; in most of the cases they have lower density than water and theirboiling points grow as their molecular weight grows, sometimes from increments of 20° to 30° for each carbon atom.Examples: 3 Benzene Colorless liquid with sweet smell. Soluble in organic solvents and dissolves in fats. Its density is 0.89 gr/cm , its fusion point is 5.5°C and its boiling point is 80°C. Naphthalene Is a white crystalline solid; can produce the characteristic smell of mothballs. Styrene Is a colorless or yellowish oily liquid. Has a sweet smell but in high concentrations can be an intense odor. Ethyl benzene Is a colorless liquid, bitter smell and flammable.4.4 Importance in life  Benzene: Benzene is used in motor fuels, industrial solvents, oils, paints and in the photographic industry. It is also used as a chemical catalyst in the production of detergent and explosives.  The explosion of this product and its vapors can produce irritation in the eyes, skin and can affect your respiratory system. If the liquid reaches the lungs, it can cause pulmonary edema and hemorrhage. If it reaches the skin it may cause dermatitis, dry or scarified.  Long exposures to benzene can cause depression in the nervous system. It can also produce dizziness, nausea, vomits, headaches; it can induce coma, and even death. It has been proven that chronic exposure to benzene may decrease red blood cells producing anemia, leukemia, and other blood ills.  Naphthalene: Naphthalene is used as a chemical intermediary or base for the synthesis of compounds used in the production of dyes; it is also used in the production of hydro-naphthalene, synthetic resin, mothballs, and celluloid. Naphthalene is also used as an insect repellent.  Ethyl Benzene: The ethyl benzene can be polymerized in order to form plastic, in the form of polystyrene. It is used in the production of resins, polyesters and insulating material, as well in cellulose acetate, styrene, synthetic oilskin, as a solvent, and gasoline component for planes and cars. As a liquid or vapor it is an irritant to the eyes, nose, throat, and skin. As a liquid if exposed to the skin it can produce dermatitis, drying or flaking your skin. Acute exposure to this benzene can produce mucus irritation in the respiratory system, mouth and nose; it can produce narcosis, cramps and respiratory palsy, and even death. The effects of a short term contact in a laboratory, can help you to react and avoid serious dangers, but may diminish your manual abilities.  Toluene: Toluene can be found in the production of benzene, and is used as substratum for phenol compounds, benzyl and its derivatives, saccharine; it is a great solvent able to dissolve paints, used as thinner or as an octane booster in gasoline fuels.  It can cause irritation in the eyes, skin and lungs. In a long term exposure the liquid can remove the skin lipids and produce dermatitis. In high levels, it may cause headaches, nausea or sleepiness.  Toluene can also produce depression to the nervous system. Its symptoms will be headaches, dizziness and fatigue, lack of coordination, sleepiness, prostration, and even coma.  Xylene: Commercial xylene is a mixture of three isomers (orto, meta and para xylene), it can also contain ethyl benzene, as well as small quantities of toluene. The meta-xylene is a clear, colorless, and flammable liquid.  It is used as a solvent in the paint industry, for cleaning liquids and fuel for planes. It can be used in the perfume industry, as an insect repellent, epoxy resins, in pharmaceutical and leather products. Xylene vapor can cause irritation in the eyes, nose and throat. Contact with the skin can produce dryness and dermatitis. Long term exposure can produce depression in the nervous system and minor reversible effects in liver and kidneys. In high concentrations can produce dizziness, sleepiness, unconsciousness. At higher concentrations may cause pulmonary edema, anorexia, vomit and abdominal pain. 9
  14. 14.  Trinitrotoluene: The 2,4,6-trinitrotoluene is a solid chemical compound with a yellow-colored surface. The main entries in the organism are via lungs or skin. At high temperatures the toxicity of this compound increases, creating instant absorption in the skin. TNT is used in bombs and other explosives. Dinitrotoluene: 2,4-dinitrotoluene and 2,6-dinitrotoluene are a pale yellow to orange crystalline solid. Both substances represent two of the six ways to name Dinitrotoluene (DNT), substance which is not naturally produced in the environment. It is used to make flexible polyurethane foams, used in furniture and mattress industries. You can make explosives, smokeless gunpowder, air bags in automobiles and dyes. A death rate higher to normal has been observed in workers that had been exposed to 2,4-dinitrotoluene, due to heart sickness, nevertheless these workers were also exposed to other chemical compounds. Dinitrotoluene can also affect the nervous system and cause irregularities in the blood cells. Benzo(alpha)pyrene: Compound which is known for many combustions, it is highly carcinogenic and mutagenic. It is used to measure air pollution, and is found in cigarette smoke. The list of aromatic hydrocarbons can continue, but what is important is that you to understand the variability of these compounds; its benefits and dangers, and the importance to investigate the products that we consume daily. 10
  15. 15. Module 2. TOPIC EXPLANATION 5. ALCOHOLS5.1 Alcohol NomenclatureAlcohols are hydrocarbons in which one or more hydrogen atoms have been replaced by an -OH group, and the carbon which containsthe –OH group can be named primary, secondary or tertiary. So, we can find saturated alcohols, unsaturated alcohols, aromatic andcyclic alcohols. Observe the following hydrocarbons and the possible alcohol that can be formed from them:You can realize that one or several hydrogen atoms can be substituted by an OH, even if it is a saturated or unsaturated compound. Thecarbon that contains the OH group can be primary and it forms a primary alcohol, if the carbon is secondary it forms a secondaryalcohol, if it is tertiary it forms a tertiary alcohol, if it is quaternary it forms a quaternary alcohol. They can be united to other carbons bya single, double or triple bond, but only one to the –OH group. They are bonded to the oxygen atom, giving them the possibility to bondto the hydrogen atom of the hydroxyl group (-OH). NOMENCLATURE OF ALCOHOLSFor single bonds: Example:Look for the parent chain, the longest chaincontaining carbons, where the –OH group islocated. Number them starting where the nearesthydroxyl group is located. Order the alkene groupsin alphabetical order, before the name rememberto put the number of the carbon where the groupis located, use the prefixes di-, tri-, etc.,corresponding to the equal number of groupsfound.As you can see, this is the same method usedwhen naming hydrocarbons, writing the numberwhere the hydroxyl group is located to name theparent chain, ending it with the suffix -ol. Thesuffixes –diol (two -OH groups), –triol (three -OHgroups), -tetraol (four -OH groups), etc., are used ifthere are multiple –OH groups in the parent chain. Example:For double or triple bonds:Look for the parent chain, containing the double and/or triplebonds, and the carbons containing the –OH groups. Numberthem starting where the nearest hydroxyl group is located.Order alphabetically the groups, and remember to writebefore the name the number of the carbon where the groupis located. Finally, write the name of the parent chain withthe suffix -ene, -yne, plus the suffix –ol, -diol, -triol, accordingto how many OH groups are found. 11
  16. 16. For cyclic hydrocarbons Example:You just need to add the suffix –ol. For compounds with abenzene ring, they are classified in a special way, namingthem phenols. The –OH group is assumed to be in carbonnumber 1, and you add the prefix phenol-. The benzene ring isa group called phenyl.5.2 PropertiesUnlike hydrocarbons, alcohols contain an –OH group, which makes alcohol’s molecule very polar, making it easy to have hydrogenbonds. This allows them to have physical properties that distinguish them from hydrocarbons.Its boiling point increases in relation with the carbons contained, but it decreases when the branching number increases.Being liquids associated, as water, they are bigger than its homogeny. For example methanol is 64.5°C and for 1,3 - Propanediol is 215°C.The solubility has the tendency to form hydrogen bonds. The smaller the alcohol, the better its solubility in water, because the –OHgroup occupies a higher percentage in the molecule. When this percentage lowers, its solubility decreases as well. Its density increaseswith the number of carbons, decreases with branching and it increases with close chains.Note: in the recommended bibliography you can find properties of other specific alcohols.5.3 ImportanceThe importance of alcohols isequal to the hydrocarbonsstudied before; in the table youcan see the uses of the mostcommon alcohols.This is the reason why ethanol isthe more studied and promotedalcohol in those countries whichdepend in exporting petroleum,who are searching for alternativeways to improve their situationand be competitive in theethanol market.A lot of countries may be opposed to ethanol production, because it is inefficient in terms of energy consumption, for example toproduce ethanol from corn, you need more energy for the production process than the ethanol produced. In our country, farmingdoesn’t produce the demands of corn needed for the Mexicans, and we are afraid that instead of giving food to people, corn will begiven to energy producers, which can be more rentable but would cause a shortage in food with consequences as the increase the priceof the tortilla, a basic element of our daily alimentation, creating a crisis among the population.Biodiesel is considered another alternative to fuel production. It has similar properties as diesel but it is obtained from a chemicalprocess combining ethanol, methanol and animal or vegetable fat. One of the advantages of biodiesel is that it can be used in dieselmotors, it is 100% biodegradable, non toxic and has no sulfur or benzene radicals as a residue.There are many other interesting fuel alternatives in the market; look for them, know its advantages and disadvantages. It is necessaryto recognize the necessity to seek for an alternative process or source of energy. It is necessary as well to examine the effects of itsresidues and intermediate products, in order to avoid the need to resolve in the future the negative issues of the new sources of energy.The importance of ethyl alcohol or ethanol increases day by day. When we analyze it, we can see that its production and use as abeverage is increasing exponentially, as well as its consequences in human health.When you drink a cup of alcohol (wine, beer or its equivalent in alcohol percentage) the organism takes one hour to digest it. If youconsume more than one cup in an hour, the concentration of alcohol in the blood increases, causing several effects in the organism.First you can experience a sense of freedom and confidence, later your motor coordination and reflexes decrease, your vocabulary isunclear with pronunciation mistakes, you lose your capacity of concentration, your mood changes from joy to sadness, your judgmentcapacity is altered as well as your perception of things, seeing or hearing things that do not exist; if the consumption is continuous in along term it can cause illnesses that can lead to death. 12
  17. 17. TOPIC EXPLANATION 6. ALDEHYDES Aldehydes are compounds containing oxygen molecules in their formula. The carbon is always primary and uses two of its bonds to unite to oxygen, remember it is not an –OH group as in alcohols. We can synthesize it by expressing its formula with an HO, which indicates that it contains the C=O group, this terminal is named carbonyl group.The structure of the carbonyl group makes the carbon to be united to three atoms by a sigma bond, due to interpolation in the sp2orbital, and they are found in 120 (as studied in Module 1). The carbon’s orbital p overlaps the oxygen to form the pi bond, by whichthe carbon and the oxygen atoms are united by a double bond and the surrounding molecule of the carbonyl is plain.6.1 NomenclatureThe carbon chains united to a carbonyl group can be any hydrocarbon that is converted in a group by losing one of its hydrogens, reasonwhy we can find in aldehydes groups that we studied in Module 1.To name them correctly look for the parent chain, the longest carbon chain which contains the carbonyl group. The chain is numbered insuch way that the aldehyde carbon is in the first position. Then locate the other alkane groups; remember to use the correspondingprefix if you have repeated groups. Sort the names in alphabetical order and finally name the parent chain using the –al suffix.If you have compounds with a ring take the ring as the base andthe carbon where the carbonyl group is located will be namedwith its corresponding prefix: alpha, orto or para.6.2 PropertiesThe carboxyl group in aldehydes is always found in the first carbon, by which this carbon is also united to a hydrogen atom. The carbonchain can give the aldehyde specific characteristics that can make it oxidize more rapidly and to react to addition. These reactions aresimpler when they are from these groups, rather than other compounds containing aldehydes which we will study later on.The polarized carbonyl group converts aldehydes in polar substances, which have a higher boiling point that its non polar homologous.Solubility in water of aldehydes depends on the longitude of the chain: if it has up to 5 carbon atoms it has a stable solubility, and withmore than 5 atoms solubility decreases exponentially. 13
  18. 18. The carbonyl group is strongly active, and takes part in many reactions. A common reaction in aldehydes is when the bond betweencarbon and oxygen breaks and a hydrogen atom is bonded to form an alcohol. To synthesize an aldehyde, the reaction of primaryalcohols is needed as shown in the following reaction:As other organic compounds that we have been studying, aldehydes can be easily found around us. Look at these examples:  It is found in aromatic compounds with some common odors that we like, such as vanilla with vanillin, cinnamon with the Cinnamaldehyde and cumin with the cuminaldehye. All of them have an aldehyde functional group.  Aldehydes are commonly present in contamination; it is one of the principal eye irritants found in smog.  In our body vitamin A is converted to cis-retinal, a substance needed so that our eye can respond to light, making them able to see. This process not only occurs in humans, but also in living organisms with visual systems.  The formaldehyde or methanal, is an aqueous solution that is used to preserve textiles in decomposition. TOPIC EXPLANATION 7. KETONES Ketones are derivatives of hydrocarbons, their structure contains two carbon atoms or hydrocarbon groups (rings or carbon structures), united to a carbonyl group (C=O). You have to be aware that this carbon is not a primary carbon. We can find them in the following forms: - Two alkane groups. - One ring and an alkane group. - Two rings.7.1 NomenclatureThere are two ways for naming ketones correctly:  IUPAC, where you always search for the parent chain, which contains the carbonyl group, and express the number of carbons contained, naming the parent alkane with the suffix –one.  Breaking the compound with the carbonyl group, and naming the parent alkane of each side, followed by the word ketone. 14
  19. 19. 7.2 PropertiesKetones contain the carbonyl group in the secondary carbons, reason why the carbon is not united to a hydrogen atom, but to anothergroup. Oxidation reactions for ketones will be more difficult than those with aldehydes, and they are less reactive in additions.The carbon of the carbonyl group can maintain its characteristics by forming bonds. The oxygen, carbonyl carbon and the two atomsunited to them are found in a 120 degree angle between them, for what it is a plane structure in this part of the molecule. This groupcan facilitate characteristics to these compounds.Inferior ketones are highly soluble in water and in organic compounds. As you can see, aldehydes and ketones have similar behavior;both have the same radical, just in a different carbon. Ketones have the same polar characteristic making their solubility, fusion andmelting points similar to aldehydes, with a little difference between compounds with the same number of carbons and similarstructures.7.3 ImportanceKetones are regularly used as solvents. The acetone is miscible in water and can dissolve many organic substances. The functional groupin ketones is found in cortisone, progesterone, and antibiotics such as tetracycline and erythromycin.Aldehydes and ketones can be found in sugars such as glucose and fructose. The propanone is used as raw material in the production ofvarnishes, lacquers, chloroform, etc., and it is usually known commercially as nail-polish remover.Some ketones, among them the acetone, are the final product of a rapid metabolism or excessive fatty acids. They are present in urine.When levels exceed normal, they can be a sign of metabolic abnormalities, including non controlled diabetes, anorexia, lowcarbohydrate or high protein diets, frequent vomiting for a long period of time, etc., allowing the identification of these diseases byurine analysis. 15
  20. 20. Module 3. Carboxylic acids, esters, ethers, amines, amides TOPIC EXPLANATION 8. CARBOXYLIC ACIDS8.1 NomenclatureThe carboxylic acids are alkyl or aromatic groups united to a carboxyl group. The carboxyl group is a carbon atom united with a doublebond to an oxygen and a simple bond to an -OH group. R–C=O Ar - C = O I R- COOH I Ar - COOH OH OHTo name them, look for the parent chain, the longest chain containing the carboxyl group. The carbon where it is located will be carbonnumber one. Look for branches or radical groups and determine the number in which they are found. Order them alphabetically, puttingbefore the number of the carbon where they are located and using the prefixes di-, tri-, etc., if necessary.Finally, name the longest chain with the –oic acid suffix.Examples: CH3 – CH2 – CH2 – COOH Butanoic acid CH3 – CH = CH - CH2 – 3-pentenoic acid COOH CH3 | 3-methyl-butanoic acid CH3 – CH – CH2 – COOH COOH – CH2– 2-phenylethanoic acidThese compounds are known since long ago, and its common names are still used. In the following list you will find some names thatmay sound familiar to you. H – COOH Formic acid CH3 – COOH Acetic acid CH3 – CH2 - COOH Propionic acid CH3 – (CH2)2 - COOH Butyric acid CH3 – (CH2)3 - COOH Valeric acid CH3 – (CH2)4 - COOH Caproic acid CH3 – (CH2)6 - COOH Caprylic acid CH3 – (CH2)8 - COOH Capric acid CH3 – (CH2)10 - COOH Lauric acid CH3 – (CH2)12 - COOH Myristic acid CH3 – (CH2)14 - COOH Palmitic acid CH3 – (CH2)7 –CH = CH - (CH2)7 - COOH Oleic acidIf you have a branched compound use the IUPAC nomenclature, but note that it does not consider the carbon in the carboxyl group, andthat instead of assigning numbers to the carbons, the Greek alphabet letters are used to name them, starting from the carbon united tothe carboxyl group.Examples: C – C – C – C –COOH     Example: CH3 – CH2 – CH – COOH -methyl butyric acid | CH3By now you can realize that there are three ways of naming the carboxylic acids, though it does not happen only in the acids, but inevery organic compound. The reason why we are explaining this situation in this module is because now you have learned how to nameorganic compounds following the IUPAC nomenclature correctly. 16
  21. 21. 8.2 PropertiesAs alcohols, aldehydes and ketones studied in the previous module, for the acid radical of carboxylic acids, the first four are soluble inwater, the fifth is partially soluble and the rest are insoluble in water. Their boiling point is higher than the compounds studied before.For example, the formic acid has a boiling point of 100.5°C.The compounds with more than eight carbons are commonly found as solid acids, unless they have a double bond; their fusion pointbegins in 8°C with the formic acid.The acetic acid is the most important of the carboxylic acids, and it is obtained from an oxidation reaction of acetaldehyde and air.Acetaldehyde is obtained from acetylene or from ethanol dehydration.8.3 ImportanceThe carboxylic acids are responsible of the sourness in fruits such as lemons, limes and pineapples, because of their content of citricacids. The odor of spoiled butter contains butyric acid and lactic acid can be found in the sour milk.Some medicines such as penicillin or aspirins contain carboxylic groups. The formic acid is the active irritant of a bee or ant bite. Theacetic acid is the vinegar used commonly and it has an important role in the formation and splitting of sugars in the metabolism.Lately some effects of the methanoic and ethanoic acid contained in the historic heritage metallic structures have been studied. TOPIC EXPLANATION 9. FUNCTIONAL GROUPS9.1 EstersEsters are compounds derived from carboxylic acids; they can be formed by replacing the –OHgroup for an O-R group or an O-Ar group. The following reactions explain their production:They can have products in any possible combination and can be For naming esters, first you have to divide the structure in twoexpressed generally by: parts, the parent alcohol and the carboxylic acid. Name first the alkyl or alcohol group and then the acid followed by the suffix - R–C=O oate. | R- COO- R O–R Example: R–C=O | R- COO- Ar O – Ar Ar – C = O Ethyl | Ar- COO- R CH3 – CH2 - COO – CH2 – CH3 propanoate O – R Ar – C = O | Ar- COO- Ar O – Ar9.2 EthersEthers are organic compounds formed by two alkyl or aryl groups connected to an oxygen atom, its general formula can be expressedas: R-O-R or Ar-O-R or Ar- O- Ar 17
  22. 22. Ether is symmetric when to each side of the oxygen you have the same alkyl or aryl group. This type of ether is produced by thedehydration of alcohols, a reaction that requires high temperatures and can be catalyzed by using sulfuric acid.In a lab, you can use the Williamson ether synthesis, where an alkyl halide reacts with an alkoxide ion (it can be sodium alkoxide orsodium fenoxide) to produce an ether. The alkyl halide is an alkane which contains a halogen or other element (X).For naming an ether, name the two substituent followed by the word ether. According to IUPAC, the shorter of the two chains becomesthe first part of the name with the –ane suffix changed to –oxy, and the longer alkane chain becomes the suffix of the name of the ether.If you have repeated chains you use the prefix -di. CH3 –O – CH3 dimethyl ether or methoxymethane CH3 – CH2 – O – CH3 ethyl methyl ether or methoxyethaneDifferent form the alcohols, ethers cannot form hydrogen bonds among each other, resulting in having lower boiling points thanalcohols.9.3 AminesThe amines are alkyl or aryl derivatives of ammonia (NH3), where one, two or three atoms of hydrogen can be replaced by a substituentsuch as alkyl or aryl groups. They are called primary, secondary or tertiary according to the number of hydrogen atoms replaced. Primary R – NH2 Ar – NH2 R–NH Ar – NH Ar – NH Secondary | | | R R Ar R–N -R Ar – N - R Ar – N – R Ar – N - Ar Tertiary | | | | R R Ar ArAmines are prepared, by reacting halides with amines or ammonia; asshown in the following reaction (Note: R can stand for an aryl or alkyl NH3 + (RX) → RNH2 + (RX) → R2NH + (RX) → R3Ngroup):The primary amines are named using the suffix –amine to the alkyl group where they are located. In the secondary or tertiary amines inwhich the alkyl groups are the same, you use the prefix di- or tri- to name the alkyl. When the secondary or tertiary amines are notsymmetric they are named using the prefix N- indicating the hydrogen substitutes. The bigger alkyl group is chosen as the base of theamine, and the substitutes in the nitrogen are indicated using the prefix N.Examples: CH3 CH3 – CH2 – NH2 : ethylamine I CH3 – N-CH-CH2 -CH3 N,N-dimethylbutan-2-amine CH3 – NH– CH3 : dimethylamine I CH3Amines are polar compounds as ammonia, which can form hydrogen bonds.  By forming hydrogen bonds in their molecules, Amines’ boiling point is higher than those non polar compounds of the same molecular weight, but they have lower boiling points than alcohols and carboxylic acids.  Amines containing less than six carbons are soluble with water; for bigger amines water solubility decreases. 18
  23. 23. 9.4 AmidesAmides are derivatives of carboxylic acids, where the –OH group is replaced by a NH2. R–C=O Ar – C = O | | NH2 NH2They are obtained from ammonia and carboxylic acids, or by ammonia substitution with an ester.For naming an amide, take the base of the carboxylic acid, changing the suffix –ic acid for the common name or the –oic acid for theIUPAC name, for the suffix –amide. CH3 – CO – NH2 : EthanamideAmides have high boiling points, similar to those in the aldehydes and ketones with similar molecular weights. TOPIC EXPLANATION 10. CHEMICAL REACTIONS I10.1 PolymerizationPolymerization is the process of uniting a large amount of small molecules in order to form abigger molecule named macromolecule. They can be natural as the polysaccharides and proteins,which we will study later on, or synthetic which are classified in: Elastomers Those polymers which have elasticity similar to rubber. Fibers Threads with great resistance. They can be molded in many forms and we find them in many Plastics objects with different forms and uses.All of the macromolecules are formed by smaller molecules; many of them are identical, or at least chemically similar. There are twogeneral methods for producing them:1. Chain-growth polymerization: is a series of reactions, each of which consume a reactive particle (it can be an anion, a cation or a freeradical) generating a similar molecule. An example is the polymerization of Ethylene: Rad + CH2 = CH2 → RadCH2 = CH2 → (CH2 =CH2) radCH2CH2CH2CH22. Step-growth polymerization: occurs when each reaction is independent from the other, but a macromolecule is formed, because thecompounds united have several groups that can react between them. From one reaction to the other there is a possibility to unite withmore molecules, forming a macromolecule.One alcohol with two –OH groups and an acid with two carboxyl groups can be united by one end, setting free the other groups to beunited again.Example:Other way to classify the polymerization is by addition, which in most cases occurs by a chain reaction; and by condensation, in whichthe process mainly occurs in steps or stages. Some synthetic polymers are polyvinyl chloride (PVC) and polyethylene; natural polymers are cotton, rubber and wood. Plastics aresynthetic resins and some of them are thermosetting, which mean that they can be softened and remodeled with heat; others arecalled thermoplastics which can be reprocessed. 19
  24. 24. Although plastics are a big source of contamination, it is important to know that this isdue to a lack of a recycling culture; industries need our help with the recollection ofmaterials to avoid the production of more garbage or waste. An easy way to do this isto know the classification system of plastics; they have a symbol of three arrowsforming a triangle with a number and letter written at its base:  PET polyethylene terephthalate  HDPE high-density polyethylene  PVC polyvinyl chloride  LDPE low-density polyethylene  PP polypropylene  PS polystyreneObserve the following table: PLASTIC MONOMER USES APPEARANCE Opaque, white as wax, it tears LDPE Ethylene Films, coatings, vases, toys, bags, food wraps. easily. Jugs for milk and vinegar, laundry detergent Low wax, it tears easily, can be HDPE Ethylene bottles (chorine, whitener, softener), dark and opaque. margarine containers. Rigid, it does not tears up easily, PP Propylene Fibers, films, jugs, lab equipment. dark color, white and soft. Credit cards, floor tiles, bright jugs, pipes. PVC Vinyl Chloride Hard sometimes with color. PVC Vinyl Chloride Same as the above. Soft as the natural skin. (polychlorinated) Adipic acid + Hard surface, creamy color, thick, Nylon Fibers, threads, clothing, surgical material. hexamethylenediamine fibers can be clear or transparent. Jugs, packing material, mugs, glasses, egg Hard and shinny, brittle, thunders PS Styrene packing. when broken. PET Soda bottles. Hard and firm.10.2 SaponificationWhen an acid and hydrogen react they produce an acid salt, as shown in the following reaction: + R – COOH + NaOH → R- COO- Na + H2OSaponification is a reaction between a long chain fatty acid and a base, which allows the production of a salt and glycerin. The saltformed is amphipathic, a molecule containing both polar and non polar portions in its structure; the first is hydrophile, soluble in water,and the other is hydrophobe but soluble in non polar solvents; this allows each end to have its own solubility behavior. Soap is anexample of this process; it allows cleaning by being soluble in water and dragging those compounds that are not. Soap has been beingproduced since a long time ago, as shown in the following reaction:Soap is a form of emulsion that contains micelle molecules, where each extreme of the molecule looks to be close to its similar andaway from the one different to it; for what the non polar are projected outside and the polar gather together in the center, as shown inthe graphic.Commercial soaps are different because they can vary in the contents of fatty acids used, or because an alcohol is added to make themcrystal clear, as well as perfume or any other ingredient. 20
  25. 25. Module 4. Petroleum, biomolecules and combustion and fermentation reactions TOPIC EXPLANATION 11. COMBUSTION11.1 CombustionCombustion is a chemical phenomenon very common to us; how many times have they put you as an example to burn paper in order toexplain that in every chemical phenomenon there is a reaction, where its compounds bond in different ways, producing newcompounds.The general reaction of a complete combustion is the following: Fuel + O2 → CO2 + H2O + EnergyWhen fuel reacts with oxygen (comburent), and with the aid of an ignition or spark, the reaction produces carbon dioxide, water andenergy. This energy is used in different forms and transformed in other types of energy.Fuels are compounds that have the capacity to burn, and arerepresented mainly by hydrocarbons, studied in the first module. Fuel Calorific valueMany of them are used in the industry and at homes. Domestic gas is (J/g)a mixture of propane and butane gases, and it is used at homes to Methane 55.6cook or in heating devices. In other means, natural gas is a mixture of Ethane 52methane, ethane, propane and butane. Gasoline is a fuel used in cars. Propane 50 Cyclopropane 49When reacting, each of these fuels produce different types of energy. Butane 49.6In the following table you can see some of the most frequent fuels Cyclobutane 48.9used and its calorific value in J/gr. Hexane 45.9 Acetylene 100As you see, the first fuels in the table are hydrocarbons that only Wood 20contain carbon (C) and hydrogen (H) in their molecule. In relation Wood charcoal 35with the other compounds, they contain other elements considered Bituminous coal 30as impurities. The oxygen comburent is generally provided from air, Gasoline 34which is composed in 21% by oxygen. In open air combustions, Kerosene 37oxygen will never be the limiting reagent, but in some cases it will be Natural Gas 50necessary to include, besides a spark, an injection of the comburent,for example in internal combustion motors.In other occasions the combustion is incomplete, as we cansee in the following reactions: Fuel + O2 → CO + H2O Fuel + O2 → C + H2OThis happens when the comburent is limited and producescarbon monoxide, a highly toxic gas, that is responsible ofmany deaths in a fire or when people use heaters in closedspaces. This incomplete reaction is also present in cigarsand the filter in them avoids complete combustion, whatmakes smokers to inhale carbon monoxide. You should beaware that high levels of carbon monoxide can be very Image obtained from: Encyclopedia Britannica, Inc. Used for educational purposes only.dangerous.Combustion is also present in living organisms. From this reaction energy is produced: the fuel is the food, after the food is digested, andall its nutrients travel to a cell where they react with the oxygen we breath, which produce a reaction generating energy so we can makeall our daily activities. 21
  26. 26. A well balanced diet will give you the opportunity to maintain a healthy body; when thefood intake is poor, we lose the possibility of giving the 100% of ourselves. If the dietcontains bigger quantities than those we need, our organism will store them as fat. Toavoid this undesired “storage”, it is important that we maintain an adequate dietaccording to our activities and we should strengthen our body with exercise.Food is often measured by the amount of calories that can generate when consumed;this is because calories are another way to measure energy… energy for our body.A good diet, in conjunction with the correct air intake when doing our daily activities,will allow our organism to be more efficient and healthy.11.2 FermentationThe way in which some anaerobic organisms produce energy is through thefermentation process. These organisms can oxidize organic compounds producingenergy; in this condition, oxidation is partial and the energy production is lower than theone generated in a combustion reaction.When you think about fermentation, generally you think about alcoholic fermentation.The production of alcoholic beverages is based on this reaction, and, like combustion, itis an oxidation reaction but its main difference is that there is no oxygen present.In the following reaction, you can see that the reactive, which is sugar, with the aid ofmicroorganisms, it can be transformed to ethanol, by the fermentation process. C6 H12 O6 → 2CH3 CH2 OH + 2CO2 + 57KcalAlcoholic beverages can be classified in wines, beers, ciders and pulque. Is the result of the complete fermentation of must or fresh grape juice in the presence of the skin of the fruit carrier ofWine the yeast. Is prepared with the juice of mature apples, adding sugar or not, depending if it is necessary, so that finally you do notCider pass the 8% of alcoholic strength needed. Is poor in alcohol content; its ingredients are: malt or barley grains, hops, starches and water, although other grainBeer cereals can be used. Caramel, sucrose and glucose may be added.Pulque Is the fermentation of cane syrup, which is extracted from the maguey or Mexican agave.Alcoholic fermentation is not the only way of fermentation. There are other types in which different microorganisms are used, and inwhich you may obtain other products. In the following table some products from these fermentations are shown: FERMENTATION PRODUCTS ORGANISMS TYPE Alcoholic Ethanol + CO2 Yeast (Saccharomyces) Lactic acid Lactic acid Lactic acid bacterias (Streptococcus, lactobacillus, etc.) Mixed acid Lactic acid, Acetic acid, Ethanol, CO2, H2 Enteric bacteria (Escherichia, Salmonella) Butanediol Butanediol, Lactic Acid, Acetic Acid, Ethanol, CO2, H2 Enteric bacteria (Aerobacter, Serratia) Butyric acid Butyric Acid, Acetic Acid, CO2, H2 Some clostridiums (Clostridium butyricum) Acetone-Butanol Acetone, Butanol, Ethanol Some clostridiums (Clostridium acetobutylicum) Propanoic acids Propanoic acids PropionibacteriumYou can also obtain fermentation in animals or even in humans. For example, when a person exercises and does not breath properly, itprovokes the muscles to form lactic acid; this person is indeed generating the needed energy, but when times passes the molecules willcrystallize and cause the well known muscular pain. 22
  27. 27. 11.3 EsterificationThe esterification is, as we studied before, the formation of esters. This reaction is considered important when analyzing the importanceof ethyl acetate, which is one of the most common monomers used in the production of plastics. This known reaction combines acarboxylic acid with an alcohol to form an ester; it is used as well with the petroleum acids, where the esterification reaction is producedby cellulose or glucose, which we will study in the next topic.Esterification from: Carboxylic acids and alcohol R – COOH + R – OH → R C OOR’ + H2O Acid anhydride R- CO-Cl + R-OH → R C OOR’ + HCl11.4 UsesIn the following table, the main uses are described according to the reaction analyzed: Reaction Uses Combustion Energy generation for air, sea and land transport means. The reaction between the fuels used in these vehicles and oxygen generates the energy which makes them move. Energy generation to form vapor, used in the thermoelectric plants to generate electric energy. In homes to cook, in barbecues to cook outside, and in fire camps. Fermentation In the production of:  Alcoholic beverages such as wines, beer, liquors, etc.  Lactic ferments such as yogurt and others.  Acetic acid fabrication. Esterification Formation of the raw materials for plastics. TOPIC EXPLANATION 12. PETROLEUMPetroleum is a mixture obtained from the subsoil of the earth and it is distributed around the world.For many years Mexico has based its economy in the extraction of this oily, dark colored substance,which is the result of the decomposition process of vegetal and animal organisms that were trappeddeep into the earth. Today, petroleum is found in soil and sea, and each time it is found in deeperplaces. Why is petroleum so valuable in this moment? Because from petroleum we can obtainsubstances which are the base of the energy used in this period of time.Actually, locating an oil field is neither easy nor risky. It is a scientific task with a well plannedstructure, based on the use of technology and instrumentation, and specialized personal.These people might have to be translated to solitary and inhospitable spots where they trace theirpaths and put communication systems to dispose the adequate transportation means for theirtransfer. Petroleum is searched following two techniques: superficial exploration and deepexploration, they both enable the existence of an oil field, which leads to make a big capitalinvestment in order to drill a petroleum field hole.In the superficial exploration vertical photography is used, which allows to find the differentvegetation and characteristics of the land, it is investigated and you can deduct a possibility of oilformation in the land. After these studies a deep exploration is made, which consist in taking samplesin different depths; they are analyzed in a laboratory or their radioactivity is checked in order tocomplete the deductive process which can conclude in the presence of petroleum.The perforation starts when the trepan, which is hollow, is screwed to a sound bar and it is impulse by a rotor table which contains aperforation column; when it is necessary the bars are increased, and when a depth of 100 or 150meters is reached a possibility ofcollapse exists, so it is put into a tube and then cement is applied, which is crucial to fasten the tube and continue until reaching the oilbank.Petroleum extraction can be given by the fluid pressure that forces its exit naturally. If this does not occur, you may use othertechniques for extraction, such as the usage of pumps, or water or gas injection. 23