Chapter 13 Alcohols Phenols and Thiols 13 1

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Chapter 13 Alcohols, Phenols, and Thiols 13. 1 Alcohols, Phenols, and Thiols General, Organic,

Chapter 13 Alcohols, Phenols, and Thiols 13. 1 Alcohols, Phenols, and Thiols General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 1

Alcohols and Phenols An alcohol contains § a hydroxyl group (—OH) attached to a

Alcohols and Phenols An alcohol contains § a hydroxyl group (—OH) attached to a carbon chain A phenol contains § a hydroxyl group (—OH) attached to a benzene ring General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 2

Classification of Alcohols are classified § by the number of alkyl groups attached to

Classification of Alcohols are classified § by the number of alkyl groups attached to the carbon bonded to the hydroxyl § as primary (1°), secondary (2°), or tertiary(3) General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 3

Learning Check Classify each alcohol as P) primary, S) secondary, or T) tertiary. A.

Learning Check Classify each alcohol as P) primary, S) secondary, or T) tertiary. A. B. CH 3—CH 2—OH C. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 4

Solution A. (S) secondary B. CH 3—CH 2—OH (P) primary C. (T) tertiary General,

Solution A. (S) secondary B. CH 3—CH 2—OH (P) primary C. (T) tertiary General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 5

Guide to Naming Alcohols General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education,

Guide to Naming Alcohols General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 6

Naming Alcohols The names of alcohols § in IUPAC system replace -e of alkane

Naming Alcohols The names of alcohols § in IUPAC system replace -e of alkane name with -ol § that are common names use the name of the alkyl group followed by alcohol Formula IUPAC CH 4 Methane CH 3─OH Methanol CH 3─CH 3 Ethane CH 3─CH 2─OH Ethanol General, Organic, and Biological Chemistry Common Name Methyl alcohol Ethyl alcohol Copyright © 2010 Pearson Education, Inc. 7

More Names of Alcohols In IUPAC names for longer carbon chains, the chain is

More Names of Alcohols In IUPAC names for longer carbon chains, the chain is numbered from the end nearer the –OH group. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 8

Some Typical Alcohols “Rubbing alcohol”: 2 -Propanol (isopropyl alcohol) Antifreeze: 1, 2 -Ethanediol (ethylene

Some Typical Alcohols “Rubbing alcohol”: 2 -Propanol (isopropyl alcohol) Antifreeze: 1, 2 -Ethanediol (ethylene glycol) Glycerol: 1, 2, 3 -Propanetriol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 9

Learning Check Give the IUPAC name for each of the following: A. CH 3—CH

Learning Check Give the IUPAC name for each of the following: A. CH 3—CH 2—CH 2—OH B. C. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 10

Solution A. CH 3—CH 2—CH 2—OH 1 -butanol STEP 1 Name the longest chain

Solution A. CH 3—CH 2—CH 2—OH 1 -butanol STEP 1 Name the longest chain attached to OH: butanol STEP 2 Number the chain from the end closer to OH: CH 3—CH 2—CH 2—OH 4 3 STEP 3 Name alcohol: General, Organic, and Biological Chemistry 2 1 1 -butanol Copyright © 2010 Pearson Education, Inc. 11

Solution (continued) B. 3 -methyl-2 -pentanol STEP 1 Name the longest chain attached to

Solution (continued) B. 3 -methyl-2 -pentanol STEP 1 Name the longest chain attached to OH: pentanol STEP 2 Number the chain from the end closer to OH: 1 2 3 4 5 STEP 3 Name alcohol and any substituents: 3 -methyl-2 -pentanol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 12

Solution (continued) C. cyclopentanol STEP 1 Name the longest chain attached to OH: cyclopentanol

Solution (continued) C. cyclopentanol STEP 1 Name the longest chain attached to OH: cyclopentanol STEP 2 Number the chain from the end closer to OH: (not necessary with one substituent) STEP 3 No substituents other than alcohol STEP 4 Name a cyclic alcohol as cycloalkanol: cyclopentanol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 13

Learning Check Draw the condensed structural formula of the following: A. 3 -Pentanol B.

Learning Check Draw the condensed structural formula of the following: A. 3 -Pentanol B. Propyl alcohol C. 3 -Methylcyclohexanol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 14

Solution Draw the condensed structural formula of the following: A. 3 -Pentanol: B. Propyl

Solution Draw the condensed structural formula of the following: A. 3 -Pentanol: B. Propyl alcohol: CH 3 —CH 2 —OH C. 3 -Methylcyclohexanol: General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 15

Phenols in Medicine Phenol § is the IUPAC name for benzene with a hydroxyl

Phenols in Medicine Phenol § is the IUPAC name for benzene with a hydroxyl group § is used in antiseptics and disinfectants Phenol Resorcinol General, Organic, and Biological Chemistry 4 -Hexylresoricinol Copyright © 2010 Pearson Education, Inc. 16

Naming Phenols To name a phenol with two substituents, § assign C-1 to the

Naming Phenols To name a phenol with two substituents, § assign C-1 to the carbon attached to the –OH § number the ring to give the lowest numbers § use prefixes o, m, and p for common names Phenol 3 -chlorophenol (m-chlorophenol) General, Organic, and Biological Chemistry 4 -bromophenol (p-bromophenol) Copyright © 2010 Pearson Education, Inc. 17

Derivatives of Phenol § Compounds of phenol are the active ingredients in the essential

Derivatives of Phenol § Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 18

Learning Check Draw the condensed structural formula of the following: A. 3 -Pentanol B.

Learning Check Draw the condensed structural formula of the following: A. 3 -Pentanol B. Ethyl alcohol C. p-Methylphenol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 19

Solution Draw the condensed structural formula of the following: A. 3 -Pentanol: B. Ethyl

Solution Draw the condensed structural formula of the following: A. 3 -Pentanol: B. Ethyl alcohol: CH 3—CH 2—OH C. p-Methylphenol: General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 20

Thiols § are organic compounds that contain a –SH group § are named in

Thiols § are organic compounds that contain a –SH group § are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 21

Naming Thiols § In thiols with long carbon chains, the chain is numbered to

Naming Thiols § In thiols with long carbon chains, the chain is numbered to locate the SH group. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 22

Sources of Thiols § often have strong odors § are used to detect gas

Sources of Thiols § often have strong odors § are used to detect gas leaks § are found in onions, oysters, and garlic General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 23

Learning Check Draw the condensed structural formula of each of the following compounds: A.

Learning Check Draw the condensed structural formula of each of the following compounds: A. 2 -Butanethiol B. 2 -Methyl-1 -butanol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 24

Solution Draw the condensed structural formula of each of the following compounds: A. 2

Solution Draw the condensed structural formula of each of the following compounds: A. 2 -Butanethiol: B. 2 -Methyl-1 -butanol: General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 25

Learning Check Name each of the following compounds: General, Organic, and Biological Chemistry Copyright

Learning Check Name each of the following compounds: General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 26

Solution Name each of the following compounds: 2 -Butanol 3 -Methyl-1 -pentanol 1 -Propanethiol

Solution Name each of the following compounds: 2 -Butanol 3 -Methyl-1 -pentanol 1 -Propanethiol General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 27

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