Chap-10A - Chapter 10 Structure and Synthesis of Alcohols...

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Chapter 10 Structure and Synthesis of Alcohols
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Chapter 10 2 10-2 Structure and Classification of Alcohols • Hydroxyl (OH) functional group • Oxygen is sp 3 hybridized.
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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.
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Chapter 10 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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Chapter 10 5 10-3 Nomenclature of Alcohols and Phenols (IUPAC) • 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. • Normally any compound’s name which ends in –ol is an alcohol of some sort
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Chapter 10 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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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) CH 2 CHCH 2 CHCH 3 OH
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Chapter 10 8 Naming Priority (p.420, Table 10-1) • Acids • Esters • Aldehydes • Ketones • Alcohols • Amines • Alkenes • Alkynes • Alkanes • Ethers • Halides
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Chapter 10 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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Chapter 10 10 10-3B 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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Chapter 10 11 10-3C Names of 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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Chapter 10 12 Glycols • 1, 2 diols (vicinal diols) are called glycols. • Common names for glycols use the name of the alkene from which they were made. CH 2 CH 2 OH OH CH 2 CH 2 CH 3 OH OH 1,2-ethanediol ethylene glycol 1,2-propanediol propylene glycol
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Chapter 10 13 10-3D Naming Phenols • -OH group is assumed to be on carbon 1. • For common names of disubstituted phenols,
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This note was uploaded on 04/08/2008 for the course CHE 201 taught by Professor Bong during the Spring '08 term at SUNY Buffalo.

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Chap-10A - Chapter 10 Structure and Synthesis of Alcohols...

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