Wade10 - Structure of Alcohols Hydroxyl (OH) functional...

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1 Structure of Alcohols Hydroxyl (OH) functional group Oxygen is sp 3 hybridized . =>
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2 Classification Primary: carbon with –OH is bonded to one other carbon. Secondary: carbon with –OH is bonded to two other carbons. Tertiary: carbon with –OH is bonded to three other carbons. Aromatic (phenol): -OH is bonded to a benzene ring. =>
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3
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4 Classify these: CH 3 CH CH 3 CH 2 OH CH 3 C CH 3 CH 3 OH OH CH 3 CH OH CH 2 CH 3 =>
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5 IUPAC Nomenclature Find the longest carbon chain containing the carbon with the -OH group. Drop the -e from the alkane name, add - ol. Number the chain, starting from the end closest to the -OH group. Number and name all substituents. =>
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6 Name these: CH 3 CH CH 3 CH 2 OH CH 3 C CH 3 CH 3 OH CH 3 CH OH CH 2 CH 3 2-methyl-1-propanol 2-methyl-2-propanol 2-butanol OH Br CH 3 3-bromo-3-methylcyclohexanol =>
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7 Unsaturated Alcohols Hydroxyl group takes precedence. Assign that carbon the lowest number. Use alkene or alkyne name. 4-penten-2-ol (old) pent-4-ene-2-ol (1997 revision of IUPAC rules) => CH 2 CHCH 2 CHCH 3 OH
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8 Naming Priority Acids Esters Aldehydes Ketones Alcohols Amines Alkenes Alkynes Alkanes Ethers Halides =>
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9 Hydroxy Substituent When -OH is part of a higher priority class of compound, it is named as hydroxy. Example: CH 2 CH 2 CH 2 COOH OH 4-hydroxybutanoic acid also known as GHB =>
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10 Common Names Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. Examples: CH 3 CH CH 3 CH 2 OH CH 3 CH OH CH 2 CH 3 isobutyl alcohol sec -butyl alcohol =>
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11 Naming Diols Two numbers are needed to locate the two -OH groups. Use -diol as suffix instead of -ol. HO OH 1,6-hexanediol =>
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12 Physical Properties Unusually high boiling points due to hydrogen bonding between molecules. Small alcohols are miscible in water, but solubility decreases as the size of the alkyl group increases. =>
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13 Boiling Points =>
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14 Solubility in Water Solubility decreases as the size of the alkyl group increases . =>
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15
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16 Methanol “Wood alcohol” Industrial production from synthesis gas Common industrial solvent Fuel at Indianapolis 500 Fire can be extinguished with water High octane rating Low emissions But, lower energy content Invisible flame =>
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17 Ethanol Fermentation of sugar and starches in grains 12-15% alcohol, then yeast cells die. Distillation produces “hard” liquors
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Wade10 - Structure of Alcohols Hydroxyl (OH) functional...

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