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Alcohol, phenol ,and ethers

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Alcohol, phenol ,and ethers Alcohol, phenol ,and ethers Presentation Transcript

  • Topic: Alcohol, Phenol, And Ethers: “Their Structures, Physical Properties and Nomenclature” Mr. Blithe
  • Structure and Physical Properties ALCOHOL An organic compound containing a hydroxyl group attached to an alkyl group. a non-polar (alkane-like) chain. a polar hydroxyl group. Alcohols have the general formula: R-OH, where ―R‖ involves a saturated C-atom (bound to hydrogen's and/or other carbons). For example:
  • Classification of alcohols • Alcohols may be classified as 1o (Primary), 2o (Secondary), or 3o (Tertiary), by considering the number of carbons bound to the hydroxyl-bearing carbon. RCH2OH R2CHOH R3COH •Ethanol is a primary alcohol because there is only one alkyl group attached to the carbon that carries the OH substituent. •The isopropyl alcohol found in rubbing alcohol is a secondary alcohol, •An example of a tertiary alcohol is tert-butyl (or t-butyl) alcohol or 2-methyl-2-propanol.
  • R-O-H has a structure similar to that of water Higher boiling points. Hydrogen Bond in Water Hydrogen Bond in Alcohol
  • Classification of alcohols We already saw that the boiling points of alkanes increase with increasing chain length. The same is true for alcohols. Alcohols with more than one hydroxyl group (polyhydroxyl alcohols) have higher boiling points than monohydroxyl alcohols. Solubility The Lower the molecular weight of alcohols, the higher the solubility in water. The water-solubility of alcohols depends on the length of the alkyl chain in the alcohol. alcohols having chains longer than four carbons are not very water-soluble. 3-4 carbons or less— ARE soluble in water
  • O CH3 O H Methanol CH3 H Alcohols having chains SHORTER than four carbons are very watersoluble…  Methanol is Soluble and Miscible in water…
  • Butanol Alcohols having chains LONGER than Three carbons are not very watersoluble…  Butanol is Soluble but not Miscible in water…
  • Solubilities of ALCOHOL in water Formula Name Solubility in Water (g/100 g) CH3OH methanol infinitely soluble CH3CH2OH ethanol infinitely soluble CH3(CH2)2OH propanol infinitely soluble CH3(CH2)3OH butanol 9 CH3(CH2)4OH pentanol 2.7 CH3(CH2)5OH hexanol 0.6 CH3(CH2)6OH heptanol 0.18 CH3(CH2)7OH octanol 0.054 CH3(CH2)9OH decanol insoluble in water
  • Comparison between the Boiling points and Solubility of ALKANES and ALCOHOLs Molecular Weigh t bp (°C) Solubility in Water Structu ral Formula N ame CH3 OH CH3 CH3 methanol ethane 32 30 65 -89 infinite ins olub le CH3 CH2 OH ethanol propane 78 -42 infinite CH3 CH2 CH3 46 44 CH3 CH2 CH2 OH CH3 CH2 CH2 CH3 1-propanol bu tane 60 58 97 0 infinite ins olub le CH3 CH2 CH2 CH2 OH 1-bu tanol 74 117 8 g/100 g CH3 CH2 CH2 CH2 CH3 pen tane 72 36 ins olub le ins olub le
  • PHENOL  Phenols are compounds in which the hydroxyl group is attached to a benzene ring.  Phenol is the simplest member of a family of compounds in which an OH group is attached directly to a benzene ring. Structure Of Phenol O H Physical properties Pure phenol is a white crystalline solid, smelling of disinfectant. The crystals are often rather wet and discolored. Phenols have the formula Ar-OH Ar must be an aromatic ring (e.g., Benzene)
  • Widely used in healthcare as: Germicides Antiseptics Disinfectants Melting and boiling points high melting and boiling points ...DocumentsMr. BLITHEDocumentsmy filesmy academic files (2013-2014)MY chem reports (organic Chem)ACTUAL REPORTattachment.pptx Hydrogen bonds can form between a lone pair on an oxygen on one molecule and the hydrogen on the -OH group of one of its neighbors. Solubility in water Phenol is moderately soluble in water - about 8 g of phenol will dissolve in 100 g of water. Phenol is somewhat soluble in water because of its ability to form hydrogen bonds with the water.
  • ETHERS Ethers are a class of organic compounds characterized by an oxygen atom connected to two hydrocarbon groups. Ethers do not H-bond with themselves, so have boiling points similar to hydrocarbons Ethers are only slightly soluble in water and are highly flammable Structure of ETHERS  An ether is a characterized by an oxygen bonded to two alkyl or aryl groups, represented here by R and R'. The substituent's can be, but do not need to be, the same.
  • Solubility Ethers can act as a hydrogen-bond acceptor, as shown in the figure on the right. But, they can't act as hydrogen-bond donors. Less likely to be soluble in water than the alcohol with the same molecular weight. The absence of an -OH group in an ether also has important consequences for its chemical properties. Ethers are essentially inert to chemical reactions. They don't react with most oxidizing or reducing agents, and they are stable to most acids and bases, except at high temperatures. However, extremely FLAMMABLE explode if exposed to air for longer periods of time, to form EXPLOSIVE PEROXIDES.
  • Melting and Boiling points Boiling points and melting points are dictated by intermolecular forces. Compared with alkane of similar molar mass, an ether will have a similar boiling point. Compared to an alcohol of the same molar mass, the ether will have a much lower boiling point.
  • Medical use of Ethers Ethers are often used as anesthetics Accumulate in the lipid material of nerve cells interfering with nerve impulse transmission. Today halogenated ethers are used routinely as general anesthetics Less flammable Safer to store and to work with
  • Nomenclature
  • ALCOHOL COMMON NAME Name the C-atoms of a single alkyl group as for alkanes. Add the word ―alcohol‖ following a space after the alkyl name. For example: 1) CH3--OH 2) CH3 CH2--OH methyl alcohol ethyl alcohol
  • IUPAC NAME
  • For example: CH3 CH3CH CH CH3 4 3 2 1 OH Butane Butanol 3-methyl-2-butanol Try this one: 1. CH3-CHCH2OH CH3 2-methyl-1-propanol
  • Alcohols with more than one OH group Polyhydroxyl alcohols possess more than one OH group. Alcohols which possess two OH groups are called ―diols‖ and those with three OH groups are called ―triols‖ Naming this kind of Compound is simple, just follow this: Alkane name + the number of the OH group For example: 1. CH2-CH-CH2 OH OH OH 1,2,3-propanetriol 1,2-Ethanediol 1,2-Propanediol 1,2,3-Propanetriol
  • Naming Alcohols…continuation 1. 2. 3. 4. Name the parent compound. Replace the –e with –ol. Number the ring to minimize number of carbon with the –OH group Identify, name, and number all substituent/s. For example: CH3 Six Carbon ring= Cyclohexane Cyclohexanol number counterclockwise Note: OH OH must be at C-1  methyl on C-3 3-methylcyclohexanol
  • PHENOL Compounds with additional substituent's are named as substituted phenols when there is only one other substituent, Ortho, Meta or Para are used. Mono-substituted phenols are characterized using the prefix ortho (o-), meta (m-) or para (p-) depending on the placement of the substituent from the hydroxyl group. ortho: (1,2-) meta :(1,3-) Cl o-chlorophenol para : (1,4-) Cl m-chlorophenol Cl p-chlorophenol
  • The simplest member of phenol is called phenol itself or hydroxybenzene and the rest are named as its derivatives. Phenol or Hydroxybenzene If there are two or more additional substituent's, each must be numbered, beginning at the OH and going in direction that gives substituent's lowest numbers (or alphabetical if same in both directions).  Functional group suffix = -common - phenol, systematic benzenol  Functional group prefix = hydroxy  di , tri and so forth are used to denote the number of substituent.
  • For example: NOTE: Many have common or trivial names that do not at all suggest the structure… OH OH 1,2-dihydroxybenzene 1,3-dihydroxybenzene NO 2 CH3 3-methylphenol NO 2 NO 2 2,4,6- trinitrophenol
  • ETHERS Common Name For common names: name each alkyl group attached to the oxygen followed by ether. For example: 1. CH3-CH2-O-CH2CH3 Diethyl Ether 2. CH3-CH2-O-CH3 Ethyl methyl Ether Methyl phenyl Ether
  • IUPAC NAME For complex ethers IUPAC names are used Step1: Name as an alkane, with larger alkyl group being the parent chain. Step 2: Find the smaller alkyl group and the O are named together as an alkoxy group (replace -yl with -oxy) e.g., CH3CH2O = ethoxy Step 3: Number chain starting at end nearest alkoxy group Step 4: Use a number to give location of alkoxy group For example: CH3CH2CH2CH2CH2-OCH3 1 Pentane Methyl=Methoxy 1-methoxypentane
  • Try this one: CH 3 1. CH3-CH2-CH2---C---CH2-CH3 O CH 3 3-methoxy-3methylhexane
  • Naming Cyclic Ethers Cyclic ethers are generally named by their common names. A cyclic ether containing two carbons is called ethylene oxide (generally known as epoxides) A cyclic ether containing 4 carbons (with 2 double bonds) is called a furan A cyclic ether containing 5 carbons (with 2 double bonds) is called a pyran A cyclic ether containing 4 carbons and 2 oxygens is called a dioxane
  • TRIVIA… PHENOLS are next-generation anti-oxidant found throughout nature in some of the healthiest foods. PHENOLS are the common health-giving link that ties together foods, such as Red Wine, Green Tea, Dark Chocolate, and SuperBerries. In human health these compounds are thought to be instrumental in combating oxidative stress, a process associated with some neurodegenerative diseases and some cardiovascular diseases.
  • Approximately 600,000 students per year are assaulted by a drinking student. Research suggests that women are more vulnerable than men to many alcohol- induced problems. Some of these include, Organ Damage, Trauma, Legal and interpersonal difficulties. Alcohol affects men and women differently. Women become more impaired than men from drinking the same amount of alcohol. This is because women: • Are generally smaller in size • Have less body water • Have less dehydrogenase. • Have more estrogen Alcohol is a central nervous system depressant. In small amounts it can have a relaxing effect.
  • Thank You for LISTENING!! !