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 =>
