Z7e Chapter 22 Organic Chemistry  pp 50 questions on online HW Stop whining! They’re not too hard (for me)
Z5e 22.1 Alkanes:  Saturated Hydrocarbons   pp <ul><li>Carbon atoms can form 4 bonds </li></ul><ul><li>Nitrogen atom can f...
Tr 114 Methane - Tetrahedral sp 3  Structure
Tr 115 Bonding in Ethene & Ethyne
Isomers <ul><li>Same  molecular  formula </li></ul><ul><li>Same  number and types  of atoms </li></ul><ul><li>Different   ...
Examples of Isomers <ul><li>The formula  C 4 H 10  has two different structures </li></ul><ul><li>  CH 3 </li></ul><ul><li...
Structural  Isomers   pp <ul><li>Compounds that have the same  molecular  formula , but different  molecular  structures ,...
Geometric Isomers   pp <ul><li>There is a  lack of rotation  around a carbon to carbon multiple bond </li></ul><ul><ul><li...
Geometric  Isomers   pp <ul><li>Differ only in the geometry of their substituted groups </li></ul><ul><li>Like other struc...
Geometric  Isomers of 1,2-dichloroethene <ul><li>Cl   Cl H   Cl  C=C   C=C   H   H Cl   H   cis trans </li></ul><ul><li>Ri...
Geometric  Isomers of chloroethene?   pp <ul><li>H   Cl H   H  C=C   C=C   H   H H   Cl   </li></ul><ul><li>Rigid structur...
Non geometric versions of 1,2-dichloroeth”ene”   pp <ul><li>Cl   Cl H   Cl  C--C   C--C   H   H Cl   H   </li></ul><ul><li...
Z5e 22.1 Alkanes:  Saturated Hydrocarbons <ul><li>Contain C and H only </li></ul><ul><li>Contain single bonds  C-C </li></...
Straight-Chain Alkanes <ul><li>Straight-chain alkanes contain any number of carbon atoms, one after the other, in a  chain...
Straight-Chain Alkanes <ul><li>Combined with the -ane ending is a prefix for the number of carbons </li></ul><ul><li>Homol...
Tr 115A Carbon-Atom Chain Prefixes
Tr 117 Some Alkanes
Straight-Chain Alkanes <ul><li>Many alkanes used for fuels: methane, propane, butane, octane </li></ul><ul><li>As the numb...
Tr 117A Straight-Chain Alkyl Groups How are alkyl groups different from their corresponding alkanes? They have one less hy...
Alkanes <ul><li>3-ethylpentane </li></ul><ul><li>2,3,4-trimethylhexane </li></ul><ul><li>Since the electrons are shared eq...
Complete Structural Formulas <ul><li>Shows the bonds between each of the atoms  </li></ul><ul><li>  H   H </li></ul><ul><l...
More Alkanes <ul><li>H  H Condensed Structural Formulas </li></ul><ul><li>H  C  C  H CH 3   CH 3 </li></ul><ul><li>H  H Et...
Naming Straight-Chain Alkanes <ul><li>Names recommended by IUPAC - the International Union of Pure and Applied Chemistry <...
Naming Straight-Chain Alkanes <ul><li>IUPAC names may be long and cumbersome </li></ul><ul><li>Common names may be easier ...
Branched-Chain Alkanes <ul><li>Branched-chain means that  other  elements besides hydrogen may be attached to the carbon <...
Branched-Chain Alkanes <ul><li>A hydrocarbon substituent is called an  alkyl group  or sometimes  radicals </li></ul><ul><...
Alkyl Groups <ul><li>Branches on carbon chains </li></ul><ul><li>H H  C   CH 3 methyl    H   </li></ul><ul><li>  H  H H  C...
Branched-Chain Alkanes   pp <ul><li>Rules for naming - page 1000 </li></ul><ul><li>1. Longest chain is the parent (tricky)...
Branched-Chain Alkanes <ul><li>Draw 2,3,5-trimethyl hexane (on board) </li></ul><ul><li>From the name,  draw  the structur...
IUPAC Names <ul><li>Name # carbons  Structural Formula </li></ul><ul><li>Meth ane 1 CH 4 </li></ul><ul><li>Eth ane 2 CH 3 ...
Cyclic Hydrocarbons <ul><li>The two ends of the carbon chain are  attached  in a  ring  in a  cyclic hydrocarbon </li></ul...
Cycloalkanes <ul><li>Cyclopropane   CH 2 </li></ul><ul><li>  CH 2  CH 2 </li></ul><ul><li>Cyclobutane CH 2  CH 2 </li></ul...
Naming Cycloalkanes with  Side Groups <ul><li>Number of  Naming side groups  </li></ul><ul><li>One Side group name goes in...
Alkane name review <ul><li>Given the alkane name, how can you draw the structural formula? </li></ul>1.  Find the root wor...
Naming Review <ul><li>What is the name of the alkyl group that contains three carbon atoms? </li></ul><ul><li>Name: CH 3 C...
Z5e 22.2 Alkenes & Alkynes <ul><li>Multiple bonds can also exist between the carbon atoms </li></ul><ul><li>Hydrocarbons c...
Tr 118 Structures of Alkenes Name ends in “-ene” Why are these called unsaturated? Less than 4 “things” on some of the car...
Naming Alkenes   pp <ul><li>Find longest parent that has the double bond in it </li></ul><ul><li>New ending: -ene </li></u...
Alkynes <ul><li>Hydrocarbons containing carbon to carbon  triple bonds  called alkynes </li></ul><ul><li>-C  C- </li></ul>...
Z5e 22.3 Aromatic Hydrocarbons <ul><li>Benzene is a six-carbon ring. </li></ul><ul><ul><li>exhibits resonance, due to loca...
Aromatic Compounds and Benzene <ul><li>Aromatic compounds contain benzene. </li></ul><ul><li>Benzene, C 6 H 6  , is repres...
Benzene Structure <ul><li>The structures for benzene can also be written as a single structure where the resonating double...
Tr 119 Resonance Structures of Benzene
Tr 118A Representations of Benzene
Aromatic Hydrocarbons <ul><li>Benzene derivatives possible: </li></ul><ul><ul><li>methylbenzene, 3-phenylhexane, ethylbenz...
Tr 119A Structural Formula for Aspirin
Naming Aromatic Compounds   pp <ul><li>Aromatic compounds are named with  benzene as the parent chain.  One side group is ...
Naming Aromatic Compounds   pp <ul><li>When two groups are attached to benzene, the ring is numbered to give the lower num...
Some Common Names   pp <ul><li>Some substituted benzene rings also use a common name.  Then naming with additional more si...
Review <ul><li>How many carbons are in a molecule of benzene? </li></ul><ul><li>Six </li></ul><ul><li>What is the name of ...
An Interlude: The Petrochemical Industry <ul><li>Fossil fuels provide much of the world’s energy </li></ul><ul><li>Natural...
Natural Gas <ul><li>Natural gas is prized for combustion, because with adequate oxygen, it burns with a hot, clean blue fl...
Petroleum <ul><li>It is separated by distillation into fractions, according to boiling pt. </li></ul><ul><li>Fractions con...
Petroleum <ul><li>The compounds found in petroleum (or crude oil) are more complex than those in natural gas </li></ul><ul...
Petroleum Refinery
Z5e 22.4 Hydrocarbon Derivatives
Functional Group <ul><li>Functional group - a specific arrangement of atoms in an organic compound capable of  characteris...
Z7e 1011 Table 22.4 Common Functional Groups   pp
Alcohols   pp <ul><li>Alcohols - a class of  organic  compounds with an -OH group </li></ul><ul><ul><li>The -OH functional...
Alcohols   pp <ul><li>Common  names: </li></ul><ul><ul><li>similar to halocarbons: Name the alkyl group followed by the wo...
Organic Chemicals <ul><li>Alcohols R- OH </li></ul><ul><li>CH 3 OH methan ol </li></ul><ul><li>(methyl alcohol) </li></ul>...
Properties of Alcohols <ul><li>Much like water, alcohols are capable of hydrogen bonding between molecules (polar). </li><...
Properties of Alcohols <ul><li>Denatured alcohol  - means it has been made poisonous by the addition of other chemicals, o...
Alcohols   pp <ul><li>Arranged into categories according to the number of R groups attached  to the carbon with the hydrox...
Naming Alcohols   pp <ul><li>A carbon compound that contain -OH (hydroxyl) group </li></ul><ul><li>In IUPAC name, the -e i...
Alcohols   pp <ul><li>The hydroxyl is given the lowest position number </li></ul><ul><li>Alcohols containing 2, 3, and 4 o...
More Names of Alcohols   pp <ul><li>IUPAC names for longer chains  number  the chain from the end nearest the -OH group. <...
Name the following alcohols: <ul><li>Name the following alcohols: </li></ul><ul><li>A.  OH   </li></ul><ul><li>CH 3 CHCHCH...
Some Typical Alcohols <ul><li>  OH </li></ul><ul><li>“ rubbing alcohol” CH 3 CHCH 3   </li></ul><ul><li>2-propanol (isopro...
Halogen Substituents <ul><li>Also known as  alkyl halides . </li></ul><ul><li>Halocarbons  - class of organic compounds co...
Chlorofluorocarbons (CFCs and the  Ozone Layer <ul><li>Ozone (O 3 ) layer absorbs most of the sun’s harmful radiation. </l...
Chlorofluorocarbons and the  Ozone Layer <ul><li>In the stratosphere, the CFCs first react with  </li></ul><ul><li>the hig...
Chlorofluorocarbons and the  Ozone Layer <ul><li>To become stable, the Cl   acquires an electron from ozone O 3  and prod...
Ethers   pp <ul><li>Contain an -O- between two carbon groups </li></ul><ul><li>Simple ethers named from -yl names of the a...
Aldehydes and Ketones   pp <ul><li>Review: </li></ul><ul><ul><li>alcohol  has an oxygen bonded to a  carbon group and a hy...
Aldehydes and Ketones   pp <ul><li>The C=O group is called the  “carbonyl group” </li></ul><ul><ul><li>it is the functiona...
Aldehydes and Ketones   pp <ul><li>Ketones  - the carbon of the carbonyl group is joined to two other carbons (meaning it ...
Aldehydes and Ketones <ul><li>In an aldehyde, an H atom is attached to a carbonyl group </li></ul><ul><li>  O carbonyl gro...
Naming Aldehydes and Ketones   pp <ul><li>Al dehydes: identify longest chain containing the carbonyl group, then the  -e  ...
Naming Aldehydes   pp <ul><li>IUPAC:  Replace the -e in the alkane name  -al </li></ul><ul><li>Common:  Add  aldehyde  to ...
Naming Ketones   pp <ul><li>In the  IUPAC  name, the -e in the alkane name is replaced with  -one </li></ul><ul><li>In the...
Aldehydes and Ketones   pp <ul><li>Neither can form intermolecular hydrogen bonds, thus a much  lower  b.p. than correspon...
Common Aldehydes and Ketones <ul><li>Benzaldehyde </li></ul><ul><li>Cinnamaldehyde </li></ul><ul><li>Vanillin </li></ul><u...
Aldehydes and Ketones <ul><li>Propanone  (common: acetone) is a good solvent; miscible with water in all proportions </li>...
Ketones <ul><li>    O O </li></ul><ul><li>      </li></ul><ul><li>Butter flavor CH 3 -C-C-CH 3  butane di one </li></ul>...
More Aldehydes as Flavorings
Review Check <ul><li>Formula for an aldehyde? </li></ul><ul><li>Which would have the highest boiling point?  a) propane  b...
Review Check <ul><li>Formula for a ketone? </li></ul><ul><li>Hydrogen-bonding cannot occur between:  a) water-alcohol  b) ...
Learning Check   <ul><li>Classify each as an aldehyde (1), ketone (2) or neither (3). </li></ul><ul><li>O </li></ul><ul><l...
Carboxylic Acids   pp <ul><li>Also have a  carb onyl group (C=O) like aldehydes and keytones, but is  also  attached to a ...
Carboxyl Group   pp <ul><li>Carboxylic acids contain the carboxyl group on carbon 1. </li></ul><ul><li>O </li></ul><ul><li...
Carboxylic Acids - look for functional group   pp
Naming Rules   pp <ul><li>Identify longest chain </li></ul><ul><li>(IUPAC) Number carboxyl carbon as 1 </li></ul><ul><li>(...
Naming Carboxylic Acids   pp <ul><li>Formula  IUPAC    Common   alkan - oic  acid   prefix –  ic  acid </li></ul><ul><li>H...
Tr 123 Fig 21.5 Carboxylic Acid:  Citric Acid How many carboxyls groups does this have? Three Why is this acidic? It can l...
Esters   pp <ul><li>In an ester, the  H  in the carboxyl group is replaced with an alkyl group </li></ul><ul><li>O </li></...
Esters   pp <ul><li>General formula: RCOOR </li></ul><ul><li>Derivatives of carboxylic acids, where the - OH  from the car...
Esters   pp <ul><li>Although polar, they do  not  form hydrogen bonds (reason: there is no hydrogen bonded to a highly ele...
Naming Esters   pp <ul><li>Naming? It has 2 words: </li></ul><ul><li>1st: Name the  alkyl  attached to the single bonded  ...
Naming Esters   pp <ul><li>Name the  alkyl  from the  alcohol –O- </li></ul><ul><li>Name the  acid  with the  C =O  with  ...
Some Esters and Their Names <ul><li>Flavor/Odor </li></ul><ul><li>Raspberries HCO OCH 2 CH 3 ethyl   methan oate (IUPAC) e...
Learning Check <ul><li>Give the IUPAC and common names of the following compound, which is responsible for the flavor and ...
Solution <ul><li>  O </li></ul><ul><li>     propyl </li></ul><ul><li>CH 3  —   C — O —CH 2 CH 2 CH 3 </li></ul><ul><li>p...
Esters in Plants <ul><li>Esters give flowers and fruits their pleasant fragances and flavors. </li></ul><ul><li>Used as fl...
Common Flavors & Odors of Esters
Amines   pp <ul><li>Organic compounds of nitrogen N </li></ul><ul><li>Classified as primary, secondary, tertiary </li></ul...
Naming Amines   pp <ul><li>IUPAC aminoalkane    Common  alkylamine </li></ul><ul><li>CH 3 CH 2 N H 2    CH 3 —NH —CH 3 </l...
Learning Check <ul><li>Give the common name and classify if primary, secondary or tertiary: </li></ul><ul><li>A.  CH 3 NH ...
DNA & RNA contain amines
Alkaloids <ul><li>Physiologically active  nitrogen -containing compounds </li></ul><ul><li>Obtained from plants </li></ul>...
Nicotine
Caffeine
Z7e 1011 Table 22.5 Common Functional Groups
Organic Reactions <ul><li>4 Types:  Substitution, addition, condensation & elimination. </li></ul><ul><li>Some (but not al...
Substitution Reactions   pp <ul><li>Halogens  on carbon chains are readily displaced by  hydroxide  ions (OH 1- ) to make ...
Substitution Reactions   pp <ul><li>CH 3 - I  + K OH     CH 3 - OH  + K I </li></ul><ul><li>CH 3 CH 2 Br  + Na OH     CH...
Addition Reactions   pp <ul><li>Carbon-carbon single bond is not easy to break </li></ul><ul><li>In double bonded alkenes,...
Fatty Acid Addition Reaction
Saturated  vs.  Unsaturated Fatty Acids
Condensation Reactions   pp <ul><li>Two molecules combine </li></ul><ul><li>Acid + Alcohol    Ester + water </li></ul><ul...
Elimination Reactions   pp <ul><li>A simple molecule like water or ammonia is removed from an organic molecule. </li></ul>
Z7e 22.5 Polymers <ul><li>large molecule formed by joining many smaller molecules together </li></ul><ul><li>Monomer </li>...
Addition Polymers <ul><li>Polymers are giant molecules, not small like the ones studied earlier in this chapter </li></ul>...
Addition Polymers <ul><li>An  addition polymer  forms when  unsaturated  monomers react to form a polymer </li></ul><ul><u...
Addition Polymers
Addition Polymers <ul><li>CH = CH 2 </li></ul><ul><li>| </li></ul><ul><li>R </li></ul>polyethylene R => H polypropylene R ...
Addition Polymers Vulcanization  - cross-linking of polyisoprene molecules that occurs when heated with sulfur. Charles Go...
Condensation Polymer   pp <ul><li>Polymer formed by molecules of  two  different compounds joining to form the large molec...
Condensation to Nylon   pp   Monomers  - hexanediamine & adipic acid Polyamide  - amide (peptide) is in the polymer Nylon ...
Nylon 66 being wound on a stirring rod
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Ch22 z5e organic

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Ch22 z5e organic

  1. 1. Z7e Chapter 22 Organic Chemistry pp 50 questions on online HW Stop whining! They’re not too hard (for me)
  2. 2. Z5e 22.1 Alkanes: Saturated Hydrocarbons pp <ul><li>Carbon atoms can form 4 bonds </li></ul><ul><li>Nitrogen atom can form 3 bonds </li></ul><ul><li>Oxygen atoms can form 2 bonds </li></ul><ul><li>Hydrogen atoms can form 1 bond </li></ul><ul><li>Useful to know when building up structures </li></ul><ul><li>Double and triple bonds count as one “effective” pair. </li></ul>
  3. 3. Tr 114 Methane - Tetrahedral sp 3 Structure
  4. 4. Tr 115 Bonding in Ethene & Ethyne
  5. 5. Isomers <ul><li>Same molecular formula </li></ul><ul><li>Same number and types of atoms </li></ul><ul><li>Different arrangement of atoms </li></ul>
  6. 6. Examples of Isomers <ul><li>The formula C 4 H 10 has two different structures </li></ul><ul><li> CH 3 </li></ul><ul><li>CH 3 CH 2 CH 2 CH 3 CH 3 C HCH 3 </li></ul><ul><li>Butane 2- methyl propane </li></ul><ul><li>When a CH 3 is is used to form a branch, it makes a new isomer of C 4 H 10 . </li></ul>
  7. 7. Structural Isomers pp <ul><li>Compounds that have the same molecular formula , but different molecular structures , are called structural isomers </li></ul><ul><li>Butane and 2-methylpropane in previous slide. </li></ul><ul><li>Also have different properties, such as b.p., m.p., and reactivity </li></ul>
  8. 8. Geometric Isomers pp <ul><li>There is a lack of rotation around a carbon to carbon multiple bond </li></ul><ul><ul><li>has an important structural implication </li></ul></ul><ul><ul><li>Two possible methyl arrangements: </li></ul></ul><ul><ul><ul><li>1. trans configuration - substituted groups on opposite sides of double bond </li></ul></ul></ul><ul><ul><ul><li>2. cis configuration - same side </li></ul></ul></ul>
  9. 9. Geometric Isomers pp <ul><li>Differ only in the geometry of their substituted groups </li></ul><ul><li>Like other structural isomers, have different physical and chemical properties </li></ul>
  10. 10. Geometric Isomers of 1,2-dichloroethene <ul><li>Cl Cl H Cl C=C C=C H H Cl H cis trans </li></ul><ul><li>Rigid structure so these are isomers with different properties. </li></ul>
  11. 11. Geometric Isomers of chloroethene? pp <ul><li>H Cl H H C=C C=C H H H Cl </li></ul><ul><li>Rigid structure BUT both carbons do NOT have two DIFFERENT groups attached to them. </li></ul><ul><li>These are just rotated in space, but are the same. </li></ul>
  12. 12. Non geometric versions of 1,2-dichloroeth”ene” pp <ul><li>Cl Cl H Cl C--C C--C H H Cl H </li></ul><ul><li>Non-rigid structure so these are NOT isomers. (The 3rd hydrogen on each carbon is not shown) </li></ul>
  13. 13. Z5e 22.1 Alkanes: Saturated Hydrocarbons <ul><li>Contain C and H only </li></ul><ul><li>Contain single bonds C-C </li></ul><ul><li>Have 4 bonds to every carbon (C) atom </li></ul><ul><li>Are nonpolar </li></ul>
  14. 14. Straight-Chain Alkanes <ul><li>Straight-chain alkanes contain any number of carbon atoms, one after the other, in a chain - meaning one linked to the next </li></ul><ul><ul><li>C-C-C C-C-C-C etc. </li></ul></ul><ul><li>Names of alk ane s always will always end with - ane </li></ul>
  15. 15. Straight-Chain Alkanes <ul><li>Combined with the -ane ending is a prefix for the number of carbons </li></ul><ul><li>Homologous series - a group of compounds that have a constant increment of change </li></ul><ul><li>In alkanes, it is: -CH 2 - </li></ul>
  16. 16. Tr 115A Carbon-Atom Chain Prefixes
  17. 17. Tr 117 Some Alkanes
  18. 18. Straight-Chain Alkanes <ul><li>Many alkanes used for fuels: methane, propane, butane, octane </li></ul><ul><li>As the number of carbons increases, so does the boiling and melting pt. </li></ul><ul><ul><li>The first 4 are gases; #5-15 are liquids; higher alkanes are solids. </li></ul></ul>
  19. 19. Tr 117A Straight-Chain Alkyl Groups How are alkyl groups different from their corresponding alkanes? They have one less hydrogen so they can bond to another atom. What would a nine-carbon alkyl group be called? Nonyl
  20. 20. Alkanes <ul><li>3-ethylpentane </li></ul><ul><li>2,3,4-trimethylhexane </li></ul><ul><li>Since the electrons are shared equally, the molecule is nonpolar </li></ul><ul><ul><li>thus, not attracted to water </li></ul></ul><ul><ul><li>oil (a hydrocarbon) not soluble in H 2 O </li></ul></ul><ul><ul><li>“ like dissolves like” </li></ul></ul>
  21. 21. Complete Structural Formulas <ul><li>Shows the bonds between each of the atoms </li></ul><ul><li> H H </li></ul><ul><li>   </li></ul><ul><li>H  C  H H C H </li></ul><ul><li>  </li></ul><ul><li>H H </li></ul><ul><li> CH 4 , methane </li></ul>
  22. 22. More Alkanes <ul><li>H H Condensed Structural Formulas </li></ul><ul><li>H C C H CH 3 CH 3 </li></ul><ul><li>H H Ethane </li></ul><ul><li> H H H </li></ul><ul><li> </li></ul><ul><li>H C C C H CH 3 CH 2 CH 3 </li></ul><ul><li> H H H Propane </li></ul>
  23. 23. Naming Straight-Chain Alkanes <ul><li>Names recommended by IUPAC - the International Union of Pure and Applied Chemistry </li></ul><ul><ul><li>end with - ane , the root part of the name indicates the # of carbons </li></ul></ul><ul><li>We sometimes still rely on common names, some of which are well-known </li></ul>
  24. 24. Naming Straight-Chain Alkanes <ul><li>IUPAC names may be long and cumbersome </li></ul><ul><li>Common names may be easier or more familiar, but usually do not describe the chemical structure! </li></ul><ul><ul><li>Methane is natural gas or swamp gas </li></ul></ul>
  25. 25. Branched-Chain Alkanes <ul><li>Branched-chain means that other elements besides hydrogen may be attached to the carbon </li></ul><ul><ul><li>halogens, oxygen, nitrogen, sulfur, etc. </li></ul></ul><ul><ul><li>any atom that takes the place of a hydrogen on a parent hydrocarbon (including another carbon) is called a substituent, or the branched part </li></ul></ul>
  26. 26. Branched-Chain Alkanes <ul><li>A hydrocarbon substituent is called an alkyl group or sometimes radicals </li></ul><ul><ul><li>use the same prefixes to indicate the number of carbons, but the -ane ending is now - yl meth yl , eth yl , prop yl , etc. </li></ul></ul><ul><li>Gives much more variety to the organic compounds </li></ul>
  27. 27. Alkyl Groups <ul><li>Branches on carbon chains </li></ul><ul><li>H H C CH 3 methyl H </li></ul><ul><li> H H H C C CH 2 CH 3 ethyl H H </li></ul>
  28. 28. Branched-Chain Alkanes pp <ul><li>Rules for naming - page 1000 </li></ul><ul><li>1. Longest chain is the parent (tricky). </li></ul><ul><li>2. Number so branches have low # of carbons. </li></ul><ul><li>3. Give position number to branch </li></ul><ul><li>4. Use prefixes if more than one branch </li></ul><ul><li>5. Alphabetize branches </li></ul><ul><li>6. Use proper punctuation ( - , ) </li></ul>
  29. 29. Branched-Chain Alkanes <ul><li>Draw 2,3,5-trimethyl hexane (on board) </li></ul><ul><li>From the name, draw the structure: </li></ul><ul><li>1. Find the parent, with the -ane </li></ul><ul><li>2. Number carbons on parent </li></ul><ul><li>3. Identify substituent groups; attach </li></ul><ul><li>4. Add remaining hydrogens </li></ul>
  30. 30. IUPAC Names <ul><li>Name # carbons Structural Formula </li></ul><ul><li>Meth ane 1 CH 4 </li></ul><ul><li>Eth ane 2 CH 3 CH 3 </li></ul><ul><li>Prop ane 3 CH 3 CH 2 CH 3 </li></ul><ul><li>But ane 4 CH 3 CH 2 CH 2 CH 3 </li></ul><ul><li>Pent ane 5 CH 3 CH 2 CH 2 CH 2 CH 3 </li></ul>
  31. 31. Cyclic Hydrocarbons <ul><li>The two ends of the carbon chain are attached in a ring in a cyclic hydrocarbon </li></ul><ul><ul><li>sample drawings on page 1066 </li></ul></ul><ul><ul><li>named as “cyclo- ____” </li></ul></ul><ul><li>hydrocarbon compounds that do NOT contain benzene rings are known as aliphatic compounds </li></ul>
  32. 32. Cycloalkanes <ul><li>Cyclopropane CH 2 </li></ul><ul><li> CH 2 CH 2 </li></ul><ul><li>Cyclobutane CH 2 CH 2 </li></ul><ul><li>CH 2 CH 2 </li></ul>
  33. 33. Naming Cycloalkanes with Side Groups <ul><li>Number of Naming side groups </li></ul><ul><li>One Side group name goes in front of the cycloalkane name. </li></ul><ul><li>Two Number the ring in the direction that gives the lowest numbers to the side groups. </li></ul>
  34. 34. Alkane name review <ul><li>Given the alkane name, how can you draw the structural formula? </li></ul>1. Find the root word (ending in -ane) in the hydrocarbon name; write the longest hydrocarbon chain to create the parent 2. Number the carbons of this parent chain 3. Identify substituents and attach them 4. Add hydrogens as necessary
  35. 35. Naming Review <ul><li>What is the name of the alkyl group that contains three carbon atoms? </li></ul><ul><li>Name: CH 3 CH 2 C(CH 3 ) 3 </li></ul><ul><li>A structural isomer of pentane is a) 2,2-dimethylpropane or b) benzene </li></ul>propyl 2,2-dimethylbutane a
  36. 36. Z5e 22.2 Alkenes & Alkynes <ul><li>Multiple bonds can also exist between the carbon atoms </li></ul><ul><li>Hydrocarbons containing carbon to carbon double bonds are called alkenes C=C C-C=C </li></ul><ul><li>Called “unsaturated” if they contain double or triple bonds (alkynes) </li></ul>
  37. 37. Tr 118 Structures of Alkenes Name ends in “-ene” Why are these called unsaturated? Less than 4 “things” on some of the carbons. Note the cis and trans isomers.
  38. 38. Naming Alkenes pp <ul><li>Find longest parent that has the double bond in it </li></ul><ul><li>New ending: -ene </li></ul><ul><li>Number the chain, so that the double bond gets the lower number </li></ul><ul><li>Name and number the substituents </li></ul><ul><li>Samples on page 1005 </li></ul>
  39. 39. Alkynes <ul><li>Hydrocarbons containing carbon to carbon triple bonds called alkynes </li></ul><ul><li>-C C- </li></ul><ul><li>Alkynes are not plentiful in nature </li></ul><ul><li>Simplest is ethyne - common name acetylene (fuel for torches) </li></ul>
  40. 40. Z5e 22.3 Aromatic Hydrocarbons <ul><li>Benzene is a six-carbon ring. </li></ul><ul><ul><li>exhibits resonance, due to location of the double and single bonds </li></ul></ul>
  41. 41. Aromatic Compounds and Benzene <ul><li>Aromatic compounds contain benzene. </li></ul><ul><li>Benzene, C 6 H 6 , is represented as a six carbon ring with 3 double bonds. </li></ul><ul><li>Two possible ways to show benzene in this form. </li></ul>
  42. 42. Benzene Structure <ul><li>The structures for benzene can also be written as a single structure where the resonating double bonds are written as a circle within the ring. </li></ul><ul><li>Benzene </li></ul><ul><li>structure </li></ul>
  43. 43. Tr 119 Resonance Structures of Benzene
  44. 44. Tr 118A Representations of Benzene
  45. 45. Aromatic Hydrocarbons <ul><li>Benzene derivatives possible: </li></ul><ul><ul><li>methylbenzene, 3-phenylhexane, ethylbenzene </li></ul></ul><ul><li>Benzene derivatives can have two or more substitutents: </li></ul><ul><ul><li>1,2-dimethylbenzene </li></ul></ul><ul><ul><li>1,3-dimethylbenzene </li></ul></ul><ul><ul><li>1,4-dimethylbenzene </li></ul></ul><ul><li>Can use ortho for 1,2; meta for 1,3; and para for 1,4 </li></ul>
  46. 46. Tr 119A Structural Formula for Aspirin
  47. 47. Naming Aromatic Compounds pp <ul><li>Aromatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene. </li></ul><ul><li> methylbenzene chlorobenzene </li></ul><ul><li>(toluene) </li></ul>
  48. 48. Naming Aromatic Compounds pp <ul><li>When two groups are attached to benzene, the ring is numbered to give the lower numbers to the side groups. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used. </li></ul>
  49. 49. Some Common Names pp <ul><li>Some substituted benzene rings also use a common name. Then naming with additional more side groups uses the ortho-, meta-, para- system. </li></ul>
  50. 50. Review <ul><li>How many carbons are in a molecule of benzene? </li></ul><ul><li>Six </li></ul><ul><li>What is the name of the alkane having 5 carbons? </li></ul><ul><li>Pentane </li></ul><ul><li>What is the substituent in the following compound: CH 3 CH 2 CH 2 CH 2 Cl </li></ul><ul><li>Cl </li></ul>
  51. 51. An Interlude: The Petrochemical Industry <ul><li>Fossil fuels provide much of the world’s energy </li></ul><ul><li>Natural gas and petroleum contain mostly aliphatic (straight-chain) hydrocarbons </li></ul><ul><li>Natural gas is an important source of alkanes of low molecular mass </li></ul>
  52. 52. Natural Gas <ul><li>Natural gas is prized for combustion, because with adequate oxygen, it burns with a hot, clean blue flame: </li></ul><ul><ul><li>CH 4 + 2O 2  CO 2 + 2H 2 O + heat </li></ul></ul><ul><li>Insufficient burning has a yellow flame, due to glowing carbon parts, as well as making carbon monoxide </li></ul>
  53. 53. Petroleum <ul><li>It is separated by distillation into fractions, according to boiling pt. </li></ul><ul><li>Fractions containing higher molar mass can be “cracked” into more useful shorter chain components, such as gasoline and kerosene </li></ul><ul><ul><li>involves catalyst and heat </li></ul></ul><ul><ul><li>starts materials for plastics and paints </li></ul></ul>
  54. 54. Petroleum <ul><li>The compounds found in petroleum (or crude oil) are more complex than those in natural gas </li></ul><ul><li>Usually straight-chain and branched-chain alkanes, with some aromatic compounds also </li></ul><ul><li>Crude oil must be refined (separated) before being used </li></ul>
  55. 55. Petroleum Refinery
  56. 56. Z5e 22.4 Hydrocarbon Derivatives
  57. 57. Functional Group <ul><li>Functional group - a specific arrangement of atoms in an organic compound capable of characteristic chemical reactions . </li></ul><ul><li>The best way to classify organic compounds. </li></ul><ul><li>Replaces an “H” in the corresponding alkane. </li></ul><ul><li>The symbol “R” is used to represent any carbon chains or rings </li></ul>
  58. 58. Z7e 1011 Table 22.4 Common Functional Groups pp
  59. 59. Alcohols pp <ul><li>Alcohols - a class of organic compounds with an -OH group </li></ul><ul><ul><li>The -OH functional group in alcohols is called a “hydroxyl” group; thus R-OH is the formula </li></ul></ul><ul><li>How is this different from the hydroxide ion? </li></ul><ul><li>The hydroxyl group is covalently bonded to the R group. Hydroxides have ionic bonding with their cations. </li></ul>
  60. 60. Alcohols pp <ul><li>Common names: </li></ul><ul><ul><li>similar to halocarbons: Name the alkyl group followed by the word alcohol </li></ul></ul><ul><ul><li>One carbon alcohol = methyl alcohol </li></ul></ul>
  61. 61. Organic Chemicals <ul><li>Alcohols R- OH </li></ul><ul><li>CH 3 OH methan ol </li></ul><ul><li>(methyl alcohol) </li></ul><ul><li>CH 3 CH 2 OH ethan ol </li></ul><ul><li>(ethyl alcohol) </li></ul><ul><li>(CH 3 ) 2 CHOH 2-propan ol </li></ul><ul><li>(isopropyl alcohol) </li></ul>
  62. 62. Properties of Alcohols <ul><li>Much like water, alcohols are capable of hydrogen bonding between molecules (polar). </li></ul><ul><ul><li>this means they will boil at a higher temperature than alkanes and halocarbons with a comparable number of atoms </li></ul></ul>
  63. 63. Properties of Alcohols <ul><li>Denatured alcohol - means it has been made poisonous by the addition of other chemicals, often methyl alcohol (methanol, or wood alcohol). </li></ul><ul><li>As little as 10 mL of methanol has been known to cause permanent blindness, and 30 ml has resulted in death!!! </li></ul>
  64. 64. Alcohols pp <ul><li>Arranged into categories according to the number of R groups attached to the carbon with the hydroxyl </li></ul><ul><ul><li>1 R group: primary alcohol </li></ul></ul><ul><ul><li>2 R groups: sec ondary alcohol </li></ul></ul><ul><ul><li>3 R groups: tert iary alcohol </li></ul></ul><ul><li>Let’s do some examples on the whiteboard (see p. 1077). </li></ul>
  65. 65. Naming Alcohols pp <ul><li>A carbon compound that contain -OH (hydroxyl) group </li></ul><ul><li>In IUPAC name, the -e in alkane name is replaced with -ol. </li></ul><ul><li>Parent is the longest chain containing the carbon with the hydroxly attached. </li></ul><ul><li>CH 4 methan e CH 3 OH methan ol (methyl alcohol) </li></ul><ul><li>CH 3 CH 3 ethan e CH 3 CH 2 OH ethan ol (ethyl alcohol ) </li></ul>
  66. 66. Alcohols pp <ul><li>The hydroxyl is given the lowest position number </li></ul><ul><li>Alcohols containing 2, 3, and 4 of the -OH substituents are named diols, triols, and tetrols respectively </li></ul>
  67. 67. More Names of Alcohols pp <ul><li>IUPAC names for longer chains number the chain from the end nearest the -OH group. </li></ul><ul><li>CH 3 CH 2 CH 2 OH 1-propanol </li></ul><ul><li>OH </li></ul><ul><li>CH 3 CHCH 3 2-propanol </li></ul><ul><li>CH 3 OH </li></ul><ul><li>CH 3 CHCH 2 CH 2 CHCH 3 5-methyl - 2 -hexan ol </li></ul>
  68. 68. Name the following alcohols: <ul><li>Name the following alcohols: </li></ul><ul><li>A. OH </li></ul><ul><li>CH 3 CHCHCH 2 CH 3 </li></ul><ul><li> CH 3 </li></ul><ul><li> OH </li></ul><ul><li>B. </li></ul>3-methyl - 2 -pentan ol cyclobutan ol
  69. 69. Some Typical Alcohols <ul><li> OH </li></ul><ul><li>“ rubbing alcohol” CH 3 CHCH 3 </li></ul><ul><li>2-propanol (isopropyl alcohol) </li></ul><ul><li>antifreeze HO-CH 2 -CH 2 -OH </li></ul><ul><li>1,2-ethane di ol (ethylene glycol) </li></ul><ul><li>OH </li></ul><ul><li>glycerol HO -CH 2 -CH-CH 2 OH (name?) </li></ul>Anti-freeze
  70. 70. Halogen Substituents <ul><li>Also known as alkyl halides . </li></ul><ul><li>Halocarbons - class of organic compounds containing covalently bonded fluorine, chlorine, bromine, or iodine. </li></ul><ul><li>Naming? Name parent as normal, add the halogen as a substituent (or prefix) </li></ul>
  71. 71. Chlorofluorocarbons (CFCs and the Ozone Layer <ul><li>Ozone (O 3 ) layer absorbs most of the sun’s harmful radiation. </li></ul><ul><li>CFCs - chlorofluorocarbons - are depleting that ozone layer. </li></ul><ul><li>CFCs are used as Freons in refrigeration, </li></ul><ul><li>air conditioning, and foam insulation. </li></ul><ul><li>Their use in spray cans is no longer allowed. </li></ul>
  72. 72. Chlorofluorocarbons and the Ozone Layer <ul><li>In the stratosphere, the CFCs first react with </li></ul><ul><li>the high-energy UV radiation from the sun </li></ul><ul><li> UV light </li></ul><ul><li>CF 2 Cl 2 CF 2 Cl  + Cl  </li></ul><ul><li>Freon-12 free radical </li></ul>
  73. 73. Chlorofluorocarbons and the Ozone Layer <ul><li>To become stable, the Cl  acquires an electron from ozone O 3 and produces ClO. Cl  + O 3 ClO + O 2 </li></ul><ul><li>The presence of ClO in the atmosphere is an indicator of the disappearance of ozone. </li></ul><ul><li>Chlorine atoms are eventually regenerated. ClO + O  Cl  + O 2 </li></ul><ul><li>Makes it possible for a single chlorine atom to destroy thousands of ozone molecules. </li></ul>
  74. 74. Ethers pp <ul><li>Contain an -O- between two carbon groups </li></ul><ul><li>Simple ethers named from -yl names of the attached groups and adding ether. </li></ul><ul><li>Naming? The two R groups are alphabetized , and followed by ether </li></ul><ul><li>Two R groups the same? Use the prefix di. </li></ul><ul><li>CH 3 -O- CH 3 di methyl ether </li></ul><ul><li>CH 3 -O- CH 2 CH 3 ethyl methyl ether </li></ul>
  75. 75. Aldehydes and Ketones pp <ul><li>Review: </li></ul><ul><ul><li>alcohol has an oxygen bonded to a carbon group and a hydrogen </li></ul></ul><ul><ul><li>ether has an oxygen bonded to two carbon groups </li></ul></ul><ul><li>An oxygen can also be bonded to a single carbon by a double bond </li></ul>
  76. 76. Aldehydes and Ketones pp <ul><li>The C=O group is called the “carbonyl group” </li></ul><ul><ul><li>it is the functional group in both aldehydes and ketones </li></ul></ul><ul><li>Aldehydes - carbonyl group always joined to at least one hydrogen ( meaning it is always on the end! ) </li></ul><ul><li>R C H O </li></ul>
  77. 77. Aldehydes and Ketones pp <ul><li>Ketones - the carbon of the carbonyl group is joined to two other carbons (meaning it is never on the end) </li></ul><ul><li>R C R O </li></ul><ul><li>See structures on pp. 1080-1081. </li></ul>
  78. 78. Aldehydes and Ketones <ul><li>In an aldehyde, an H atom is attached to a carbonyl group </li></ul><ul><li> O carbonyl group </li></ul><ul><li> </li></ul><ul><li> CH 3 - C- H </li></ul><ul><li>In a ketone, two carbon groups are attached to a carbonyl group </li></ul><ul><li> O carbonyl group </li></ul><ul><li> </li></ul><ul><li> CH 3 - C- CH 3 </li></ul>
  79. 79. Naming Aldehydes and Ketones pp <ul><li>Al dehydes: identify longest chain containing the carbonyl group, then the -e ending replaced by - al </li></ul><ul><li>methan al , ethan al , etc. </li></ul><ul><li>ket one s: longest chain w/carbonyl, then new ending of - one ; number it </li></ul><ul><li>propan one , 2-pentan one , 3-pentan one </li></ul>
  80. 80. Naming Aldehydes pp <ul><li>IUPAC: Replace the -e in the alkane name -al </li></ul><ul><li>Common: Add aldehyde to the prefixes form (1C), acet (2C), propion(3), and butry(4C) </li></ul><ul><li> O O O </li></ul><ul><li>   </li></ul><ul><li>H-C- H CH 3 -C- H CH 3 CH 2 C- H </li></ul><ul><li>methan al ethan al propan al </li></ul><ul><li>(form aldehyde ) (acet aldehyde ) (propion aldehyde ) </li></ul>
  81. 81. Naming Ketones pp <ul><li>In the IUPAC name, the -e in the alkane name is replaced with -one </li></ul><ul><li>In the common name, add the word ketone after naming the alkyl groups attached to the carbonyl group </li></ul><ul><li> O O </li></ul><ul><li>  </li></ul><ul><li>CH 3 -C- CH 3 CH 3 -C- CH 2 -CH 3 </li></ul><ul><li>Propan one 2-Butan one </li></ul><ul><li>( Dimethyl ketone) (Ethyl methyl ketone) </li></ul>
  82. 82. Aldehydes and Ketones pp <ul><li>Neither can form intermolecular hydrogen bonds, thus a much lower b.p. than corresponding alcohols </li></ul><ul><li>Wide variety have been isolated from plants and animals; possible fragrant odor or taste; many common names </li></ul>
  83. 83. Common Aldehydes and Ketones <ul><li>Benzaldehyde </li></ul><ul><li>Cinnamaldehyde </li></ul><ul><li>Vanillin </li></ul><ul><li>Methanal (common: formaldehyde) </li></ul><ul><ul><li>40% in water = formalin, a preservative </li></ul></ul>
  84. 84. Aldehydes and Ketones <ul><li>Propanone (common: acetone) is a good solvent; miscible with water in all proportions </li></ul><ul><li>Why is it a good substance used in nail-polish removers? . . . </li></ul><ul><li>Good solvent for nonpolar substances also. </li></ul>
  85. 85. Ketones <ul><li> O O </li></ul><ul><li>   </li></ul><ul><li>Butter flavor CH 3 -C-C-CH 3 butane di one </li></ul><ul><li> O </li></ul><ul><li>  </li></ul><ul><li>Clove flavor CH 3 -C-CH 2 CH 2 CH 2 CH 2 CH 3 </li></ul><ul><li>2-heptanone </li></ul>
  86. 86. More Aldehydes as Flavorings
  87. 87. Review Check <ul><li>Formula for an aldehyde? </li></ul><ul><li>Which would have the highest boiling point? a) propane b) 1-propanol </li></ul><ul><li>Name: CH 3 CH 2 OCH 2 CH 3 </li></ul><ul><li>Phenols are characterized by: </li></ul>( b ) ( diethyl ether ) ( an -OH group on a benzene ring ) O R - C - H
  88. 88. Review Check <ul><li>Formula for a ketone? </li></ul><ul><li>Hydrogen-bonding cannot occur between: a) water-alcohol b) water-alkane </li></ul><ul><li>O </li></ul><ul><li>Name: CH 3 CCH 2 CH 3 </li></ul>O R - C - R ( b ) ( 2-butanone )
  89. 89. Learning Check <ul><li>Classify each as an aldehyde (1), ketone (2) or neither (3). </li></ul><ul><li>O </li></ul><ul><li>  </li></ul><ul><li>A. CH 3 CH 2 CCH 3 B. CH 3 -O-CH 3 </li></ul><ul><li> CH 3 O </li></ul><ul><li>  </li></ul><ul><li>C. CH 3 -C-CH 2 CH D. </li></ul><ul><li> </li></ul><ul><li> CH 3 </li></ul>2 2 3 1
  90. 90. Carboxylic Acids pp <ul><li>Also have a carb onyl group (C=O) like aldehydes and keytones, but is also attached to a hydr oxyl group (-OH) = “ carboxyl ” group </li></ul><ul><li>general formula: R-COOH </li></ul><ul><ul><li>weak acids (ionize slightly) </li></ul></ul><ul><li>Named by replacing -e with - oic and followed by the word acid </li></ul><ul><li>methan oic acid; ethan oic acid </li></ul>
  91. 91. Carboxyl Group pp <ul><li>Carboxylic acids contain the carboxyl group on carbon 1. </li></ul><ul><li>O </li></ul><ul><li>  </li></ul><ul><li>CH 3 — C —OH = CH 3 — COOH </li></ul><ul><li>carboxyl group </li></ul>
  92. 92. Carboxylic Acids - look for functional group pp
  93. 93. Naming Rules pp <ul><li>Identify longest chain </li></ul><ul><li>(IUPAC) Number carboxyl carbon as 1 </li></ul><ul><li>(Common) Assign  ,  ,  to carbon atoms adjacent to carboxyl carbon </li></ul><ul><li>CH 3 </li></ul><ul><li> | </li></ul><ul><li>CH 3 — CH —CH 2 —COOH </li></ul><ul><li>IUPAC 3-methylbutanoic acid </li></ul><ul><li>Common  -methylbutryic acid </li></ul>
  94. 94. Naming Carboxylic Acids pp <ul><li>Formula IUPAC Common alkan - oic acid prefix – ic acid </li></ul><ul><li>HCOOH methanoic acid formic acid </li></ul><ul><li>CH 3 COOH ethanoic acid acetic acid </li></ul><ul><li>CH 3 CH 2 COOH propanoic acid propionic acid </li></ul><ul><li>CH 3 CH 2 CH 2 COOH butanoic acid butyric acid </li></ul>
  95. 95. Tr 123 Fig 21.5 Carboxylic Acid: Citric Acid How many carboxyls groups does this have? Three Why is this acidic? It can lose a hydrogen ion. How does it affect the taste of citrus fruits? Acids give a sour taste.
  96. 96. Esters pp <ul><li>In an ester, the H in the carboxyl group is replaced with an alkyl group </li></ul><ul><li>O </li></ul><ul><li>  </li></ul><ul><li>CH 3 — C — O —CH 3 = CH 3 — COO —CH 3 </li></ul><ul><li>ester group </li></ul>
  97. 97. Esters pp <ul><li>General formula: RCOOR </li></ul><ul><li>Derivatives of carboxylic acids, where the - OH from the carboxyl group is replaced by an - OR from an alcohol: </li></ul><ul><ul><li>carboxylic acid + alcohol  ester + water </li></ul></ul><ul><li>Usually a trace of mineral acid added as catalyst (acids are dehydrating agents) </li></ul><ul><li>many esters have pleasant, fruity odors- banana, pineapple, perfumes </li></ul><ul><li>Lab 25 is an ester lab. See website for special instructions . </li></ul>
  98. 98. Esters pp <ul><li>Although polar, they do not form hydrogen bonds (reason: there is no hydrogen bonded to a highly electronegative atom) </li></ul><ul><ul><li>thus, much lower b.p. than the hydrogen-bonded carboxylic acids they came from! </li></ul></ul>
  99. 99. Naming Esters pp <ul><li>Naming? It has 2 words: </li></ul><ul><li>1st: Name the alkyl attached to the single bonded oxygen from the alcohol . </li></ul><ul><li>2nd: take the acid name , remove the -oic acid , add -oate . </li></ul><ul><li> O CH 3 CH 2 C O CH 2 CH 3 </li></ul><ul><li>Ethyl propanoate </li></ul>
  100. 100. Naming Esters pp <ul><li>Name the alkyl from the alcohol –O- </li></ul><ul><li>Name the acid with the C =O with –ate </li></ul><ul><li>acid alcohol </li></ul><ul><li> O </li></ul><ul><li>  methyl </li></ul><ul><li>CH 3 — C — O — CH 3 </li></ul><ul><li>Ethan oate methyl eth anoate (IUPAC) </li></ul><ul><li>(acetate) methyl acetate (common) </li></ul>
  101. 101. Some Esters and Their Names <ul><li>Flavor/Odor </li></ul><ul><li>Raspberries HCO OCH 2 CH 3 ethyl methan oate (IUPAC) ethyl formate (common) </li></ul><ul><li>Pineapples CH 3 CH 2 CH 2 CO OCH 2 CH 3 ethyl butan oate (IUPAC) ethyl butyrate (common) </li></ul>
  102. 102. Learning Check <ul><li>Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears . . . </li></ul><ul><li> O </li></ul><ul><li>  </li></ul><ul><li>CH 3 — C — O —CH 2 CH 2 CH 3 </li></ul>
  103. 103. Solution <ul><li> O </li></ul><ul><li>  propyl </li></ul><ul><li>CH 3 — C — O —CH 2 CH 2 CH 3 </li></ul><ul><li>propyl ethan oate (IUPAC) </li></ul><ul><li>propyl acetate (common) </li></ul>
  104. 104. Esters in Plants <ul><li>Esters give flowers and fruits their pleasant fragances and flavors. </li></ul><ul><li>Used as flavoring agents. </li></ul>
  105. 105. Common Flavors & Odors of Esters
  106. 106. Amines pp <ul><li>Organic compounds of nitrogen N </li></ul><ul><li>Classified as primary, secondary, tertiary </li></ul><ul><li> C H 3 C H 3 </li></ul><ul><li>C H 3 — N H 2 C H 3 — N H C H 3 — N — C H 3 1° 2° 3° </li></ul>
  107. 107. Naming Amines pp <ul><li>IUPAC aminoalkane Common alkylamine </li></ul><ul><li>CH 3 CH 2 N H 2 CH 3 —NH —CH 3 </li></ul><ul><li>aminoethane N -methylaminomethane </li></ul><ul><li>(ethylamine) (d imethylamine) </li></ul><ul><li>N H 2 </li></ul><ul><li> | </li></ul><ul><li>CH 3 CHCH 3 </li></ul><ul><li>2-aminopropane </li></ul><ul><li>(isopropylamine) Aniline N -methylaniline </li></ul>
  108. 108. Learning Check <ul><li>Give the common name and classify if primary, secondary or tertiary: </li></ul><ul><li>A. CH 3 NH CH 2 CH 3 . . . </li></ul><ul><li> </li></ul><ul><li> CH 3 | B. CH 3 CH 2 N CH 3 . . . </li></ul>ethyl methyl amine , 2° ethyl dimethyl amine , 3°
  109. 109. DNA & RNA contain amines
  110. 110. Alkaloids <ul><li>Physiologically active nitrogen -containing compounds </li></ul><ul><li>Obtained from plants </li></ul><ul><li>Used as anesthetics, antidepressants, and stimulants </li></ul><ul><li>Many are addictive </li></ul>
  111. 111. Nicotine
  112. 112. Caffeine
  113. 113. Z7e 1011 Table 22.5 Common Functional Groups
  114. 114. Organic Reactions <ul><li>4 Types: Substitution, addition, condensation & elimination. </li></ul><ul><li>Some (but not all) of this can be found on page 1003 & 1007 of Z7e. </li></ul>
  115. 115. Substitution Reactions pp <ul><li>Halogens on carbon chains are readily displaced by hydroxide ions (OH 1- ) to make an alcohol + a salt: </li></ul><ul><ul><li>R- X + OH 1-  R- OH + X 1- </li></ul></ul>
  116. 116. Substitution Reactions pp <ul><li>CH 3 - I + K OH  CH 3 - OH + K I </li></ul><ul><li>CH 3 CH 2 Br + Na OH  CH 3 CH 2 OH + Na Br </li></ul>Iodomethane Methanol Bromoethane Ethanol
  117. 117. Addition Reactions pp <ul><li>Carbon-carbon single bond is not easy to break </li></ul><ul><li>In double bonded alkenes, it is easier to break a bond </li></ul><ul><li>Addition reaction - substance is added at the double or triple bond location, after it is broken </li></ul><ul><li>CH 3 CH=CHCH 3 + H 2  CH3CH 2 CH 2 CH3 </li></ul>
  118. 118. Fatty Acid Addition Reaction
  119. 119. Saturated vs. Unsaturated Fatty Acids
  120. 120. Condensation Reactions pp <ul><li>Two molecules combine </li></ul><ul><li>Acid + Alcohol  Ester + water </li></ul><ul><li>HCO OH + H OCH 3  HCOOCH 3 + H 2 O </li></ul>
  121. 121. Elimination Reactions pp <ul><li>A simple molecule like water or ammonia is removed from an organic molecule. </li></ul>
  122. 122. Z7e 22.5 Polymers <ul><li>large molecule formed by joining many smaller molecules together </li></ul><ul><li>Monomer </li></ul><ul><li>small molecules which are joined together to form a polymer </li></ul>
  123. 123. Addition Polymers <ul><li>Polymers are giant molecules, not small like the ones studied earlier in this chapter </li></ul><ul><li>Examples are plastics </li></ul><ul><li>Polymer - large molecule formed by the covalent bonding of smaller molecules called monomers </li></ul>
  124. 124. Addition Polymers <ul><li>An addition polymer forms when unsaturated monomers react to form a polymer </li></ul><ul><ul><li>ethene will form polyethylene , see next slide. </li></ul></ul><ul><ul><li>polyethylene is easy to clean, chemically resistant - milk bottles, plastic wrap, refrigerator dishes </li></ul></ul>
  125. 125. Addition Polymers
  126. 126. Addition Polymers <ul><li>CH = CH 2 </li></ul><ul><li>| </li></ul><ul><li>R </li></ul>polyethylene R => H polypropylene R => CH 3 polyvinylchloride R => Cl polystyrene R => benzene ring
  127. 127. Addition Polymers Vulcanization - cross-linking of polyisoprene molecules that occurs when heated with sulfur. Charles Goodyear accidentally discovered this and used it to make synthetic rubber for tires, etc.
  128. 128. Condensation Polymer pp <ul><li>Polymer formed by molecules of two different compounds joining to form the large molecule </li></ul><ul><li>One compound usually has an amine functional group </li></ul><ul><li>Other molecule has carboxylic acid functional group </li></ul><ul><li>Split out water molecule to form peptide linkage O H C N </li></ul>
  129. 129. Condensation to Nylon pp Monomers - hexanediamine & adipic acid Polyamide - amide (peptide) is in the polymer Nylon 66 - each monomer has 6 carbon atoms Polyester is another type of condensation polymer
  130. 130. Nylon 66 being wound on a stirring rod

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