《国外有机化学》 英文版 Chapter 10 Structure and Synthesis of Alcohols

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 c 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 0.96 1.4A 0.96 A H H 104.5°H S、1089H water water HH methyl alcohol methyl alcohol Hydroxyl(oh) functional group Oxygen is sp hybridized Chapter 10

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

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 CH CH CH3-Ch-CHOH CH3-C-OH CH OH OH CH3--CH-CH2CH3 = 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 o Number the chain, starting from the end closest to the-Oh group Number and name all substituents, = Chapter 10

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 CH OH CH3--CH-CH2OH CH3--CH-CH2CH3 2-methyl-1-propanol 2-butanol CH3 OH CH3-C-OH CH Br CHa 2-methyl-2-propanol 3-bromo-3-methylcyclohexanol > Chapter 10

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

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 ·A| cools Halides Amines => Chapter 10

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 CH CHCH, COOH also known as GHB 4-hydroxybutanoic acid Chapter 10

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: CH OH CH3-CH—CH2OH CH3-CH-CH2 CH3 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 =>