Organic Chemistry,5th Edition L.G.Wade,Jr. Chapter 10 Structure and Synthesis of Alcohols Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2003，Prentice Hall
Chapter 10 Structure and Synthesis of Alcohols Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2003, Prentice Hall Organic Chemistry, 5th Edition L. G. Wade, Jr
Structure of Alcohols 0.96A .4 0.96A H 104.50 H 108.9° H water water HH methyl alcohol methyl alcohol 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. =>
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. => 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. =>
Classify these: CH3 CH3 CH3一CH-CHOH CH3-C-OH OH OH CH3-CH-CH2CH3 二> Chapter 10
Chapter 10 4 Classify these: CH3 CH CH3 CH2OH CH3 C CH3 CH3 OH OH CH3 CH OH CH2CH3 =>
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.= 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. =>
Name these: CH3 OH CH3一CH-CHOH CH3-CH-CH2CH3 2-methyl-1-propanol 2-butanol CH3 OH CH3-C-OH CH3 Br CH3 2-methyl-2-propanol 3-bromo-3-methylcyclohexanol => 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-methyl-2-propanol 2-butanol OH Br CH3 3-bromo-3-methylcyclohexanol =>
Unsaturated Alcohols Hydroxyl group takes precedence.Assign that carbon the lowest number. Use alkene or alkyne name. OH CH2-CHCH2CHCH3 4-penten-2-ol (old) pent-4-ene-2-ol (1997 revision of IUPAC rules) => Chapter 10 7
Chapter 10 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) => CH2 CHCH2 CHCH3 OH
Naming Priority ·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 =>
Hydroxy Substituent When-OH is part of a higher priority class of compound,it is named as hydroxy. ·Example: OH CH2CHCHCOOH 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 =>
Common Names Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. 。Examples: CH3 OH CH3一CH-CH2OH CH3-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 =>