1.4A 0.96A Organic Chemistry,6th Edition H L.G.Wade,Jr. 108.9° H H H Chapter 10 Structure and Synthesis of Alcohols Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2006，Prentice Hall
Chapter 10 Structure and Synthesis of Alcohols Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2006, Prentice Hall Organic Chemistry, 6th Edition L. G. Wade, Jr
14 0.96A Structure of Alcohols 108.9° H H 0.96A 1.4 0.96A H 104.50 H 108.9° H water H water H methyl alcohol methyl alcohol Copyright 2005 Pearson Prentice Hall,Inc. Hydroxyl (-OH)functional group Oxygen is sp3 hybridized. => Chapter 10 2
Chapter 10 2 Structure of Alcohols • Hydroxyl (-OH) functional group • Oxygen is sp3 hybridized. =>
1.4A 0.96A Classification 108.9° H HH 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. => Chapter 10 3
Chapter 10 3 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. =>
1.4 0.96A Classify these: 108.9° H H CH3 CH3 CH3-CH-CH2OH CH3- C-OH CH OH OH CH3-CH-CH2CH; => Chapter 10 4
Chapter 10 4 Classify these: CH3 CH CH3 CH2OH CH3 C CH3 CH3 OH OH CH3 CH OH CH2CH3 =>
1.4 0.96A H IUPAC Nomenclature 108.9° H H H 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.= Chapter 10 5
Chapter 10 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. =>
1.4 0.96A H Name these: 108.9° H CH3 OH CH3-CH-CH2OH CH3-CH-CH2CH3 2-methyl-1-propanol 2-butanol 2-methylpropan-1-ol butan-2-ol OH CH3 CH3一C-OH CH3 Br CH3 2-methyl-2-propanol 3-bromo-3-methylcyclohexanol 2-methylpropan-2-ol 3-bromo-3-methylcyclohexan-1-ol => Chapter 10 6
Chapter 10 6 Name these: CH3 CH CH3 CH2OH CH3 C CH3 CH3 OH CH3 CH OH CH2CH3 2-methyl-1-propanol 2-methylpropan-1-ol 2-methyl-2-propanol 2-methylpropan-2-ol 2-butanol butan-2-ol OH Br CH3 3-bromo-3-methylcyclohexanol 3-bromo-3-methylcyclohexan-1-ol =>
1.4A 0.96A H Unsaturated Alcohols 108.9° H H Hydroxyl group takes precedence.Assign that carbon the lowest number. Use alkene or alkyne name. OH CH2-CHCH-CHCH3 4-penten-2-ol pent-4-ene-2-ol => Chapter 10
Chapter 10 7 Unsaturated Alcohols • Hydroxyl group takes precedence. Assign that carbon the lowest number. • Use alkene or alkyne name. 4-penten-2-ol pent-4-ene-2-ol => CH2 CHCH2 CHCH3 OH
1.4A 0.96A Naming Priority 108.9° H H ·Acids ·Alkenes ·Esters ·Alkynes ·Aldehydes ·Alkanes ·Ketones ·Ethers ·Alcohols ·Halides ·Amines > Chapter 10 8
Chapter 10 8 Naming Priority • Acids • Esters • Aldehydes • Ketones • Alcohols • Amines • Alkenes • Alkynes • Alkanes • Ethers • Halides =>
1.4A 0.96A Hydroxy Substituent 108.9° H H H When-OH is part of a higher priority class of compound,it is named as hydroxy. 。Example: OH CHCHCHCOOH also known as GHB 4-hydroxybutanoic acid => Chapter 10 9
Chapter 10 9 Hydroxy Substituent • When -OH is part of a higher priority class of compound, it is named as hydroxy. • Example: CH2 CH2 CH2 COOH OH 4-hydroxybutanoic acid also known as GHB =>
1.4A 0.96A Common Names 108.9° H H Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. 。Examples: CH3 OH CH3一CH-CH2OH CH3一CH-CH2CH3 isobutyl alcohol sec-butyl alcohol => Chapter 10 10
Chapter 10 10 Common Names • Alcohol can be named as alkyl alcohol. • Useful only for small alkyl groups. • Examples: CH3 CH CH3 CH2OH CH3 CH OH CH2CH3 isobutyl alcohol sec-butyl alcohol =>