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1 Copyright © 2004 Pearson Education Inc., publishing as Benjamin Cummings.

Structure and Classification of Alcohols

14.3 Naming Alcohols, Phenols, and Thiols14.4 Some Important Alcohols and Phenols

Alcohols

In an alcohol, a

hydroxyl group ( - OH) is attached to a carbon chain.

In a phenol, a

Alcohols are classified as primary, secondary, or

tertiary.Classification is determined by the number of

alkyl groups attached to the carbon bonded to the hydroxyl.Primary (1º) Secondary (2º) Tertiary (3º)1 group 2 groups 3 groups

HCH 3 CH 3 CH 3

C - OH CH

3 - C - OHCH 3 - C - OH H H CH 3

Classification of Alcohols

A. ___CH

3 - CH - CH 2 - CH 3

B. ___ CH

3 - CH 2 - CH 2 - OH

C. ____HO - CH

2 - CH 2 - CH 2 - CH 2 - CH 3

Learning Check

5 Copyright © 2004 Pearson Education Inc., publishing as Benjamin Cummings. Classify each alcohol as 1) primary, 2) secondary, or 3) tertiary. OH A. 2 CH 3 - CH - CH 2 - CH 3 B. 1 CH 3 - CH 2 - CH 2 - OH C. 1

HO - CH

2 - CH 2 - CH 2 - CH 2 - CH 3

Solution

The IUPAC system replaces the -ein the

name of the alkane main chain with-ol. Common names for simple alcohols use the alkyl name followed by alcohol.CH 4 methan eCH 3 OH methan ol (methyl alcohol) CH 3 CH 3 ethane CH 3 CH 2 OH ethanol (ethyl alcohol)

Naming Alcohols

In the IUPAC names for longer chains, the chain

is numbered from the end nearest the -OH group.CH 3 - CH 2 - CH 2

OH1-propanol

OH CH 3 - CH - CH 2 - CH 3

2-butanol

CH 3 OH CH 3 - CH - CH 2 - CH - CH 3

4-methyl-2-pentanol

Naming Alcohols

2-propanol (isopropyl alcohol)

antifreeze HO - CH 2 - CH 2 - OH

1,2-ethanediol (ethylene glycol)

OH glycerol HO - CH 2 - CH - CH 2 - OH

1,2,3-propanetriol

Some Typical Alcohols

Name the following:

A. CH

3 - CH 2 - CH 2 - CH 2 - OH

OH CH

3 B. CH 3 - CH - CH - CH 2 - CH 3 C. OH

Learning Check

A. CH

3 - CH 2 - CH 2 - CH 2 - OH

1-butanol

OH CH

B. CH

3 - CH - CH - CH 2 - CH 3

3-methyl-2-pentanol

C.cyclopentanol

Solution

Write the structure of each of the following:A. 3-pentanolB. ethyl alcoholC. 3-methylcyclohexanol

Learning Check

Write the structure of the following:

A. 3-pentanol

OH CH 3 - CH 2 - CH - CH 2 - CH 3

B. ethyl alcohol

CH 3 - CH 2 - OH

C. 3-methylcyclohexanol

OH CH 3

Solution

Alcohols undergo combustion with O

2 to produce CO 2 and H 2 O. 2CH 3

OH + 3O

2 2CO 2 + 4H 2

O + Heat

Dehydrationremoves H- and -OH from adjacent

carbon atoms by heating with an acid catalyst.

H OH

| | H , heat

H - C - C - H H - C=C - H + H

2 O

H H H H

alcoholalkene

14.5Reactions of Alcohols

Formation of Ethers

Ethers form when dehydration takes place at low

temperature. H CH 3 - OH + HO - CH 3 CH 3 - O - CH 3 + H 2 O

Two Methanol Dimethyl ether

Oxidation and Reduction

In organic chemistry, oxidationis a loss of

hydrogen atoms or a gain of oxygen.

In an oxidation, there is an increase in the

number of C-O bonds.

Reductionis a gain of hydrogen or a loss of

In the oxidation [O] of a primary alcohol, one H

is lost from the -OH and another H from the carbon bonded to the OH.[O]

Primary alcoholAldehyde

OHO |[O]|| CH 3 - C - HCH 3 - C - H + H 2 O H

EthanolEthanal

(ethyl alcohol)(acetaldehyde)

Oxidation of Primary Alcohols

The oxidation of a secondary alcohol removes one H from -OH and another H from the carbon bonded to the -OH.

[O]

Secondary alcoholKetone

OHO|[O]||CH

3 - C - CH 3 CH 3 - C - CH 3 H 2 O|H

2-PropanolPropanone(Isopropyl alcohol)(Dimethylketone; Acetone)

Oxidation of Secondary Alcohols

Tertiary alcohols are resistant to oxidation.

[O]

Tertiary alcoholsno reaction

OH |[O] CH 3 - C - CH 3 no product CH 3 no H on the C-OH to oxidize

2-Methyl-2-propanol

Oxidation of Tertiary Alcohols

3 CH 2 CH 2

OH with the following

reagents: A. H , heat

B. [O]C. O

2 , spark

Learning Check

B. [O]3) CH

3 - CH 2 - C - H

C. O

2 spark2) CO 2 + H 2 O

Solution

people than any other drug.

Is metabolized at a rate of

12-15 mg/dL per hour by a social drinker.

Is metabolized at a rate of 30

mg/dL per hour by an alcoholic.

Ethanol CH

Enzymes in the liver oxidize ethanol.

The aldehyde produced impairs coordination.

A blood alcohol level over 0.4% can be fatal.

O CH 3 CH 2

OH CH

CH 2CO

2 + H 2 O

Ethyl alcohol acetaldehyde

Oxidation of Alcohol in the Body

Effect of Alcohol on the Body

% Ethanol Product50%Whiskey, rum, brandy40%Flavoring extracts15-25% Listerine, Nyquil, Scope12%Wine, Dristan, Cepacol3-9%Beer, Lavoris

Alcohol Contents in Common

Products

14.6Phenols

A phenol is a benzene ring with a hydroxyl group.

For two substituents, assign C-1 to the carbon

attached to the -OH.

Number the ring to give the lowest numbers.

The prefixes

Examples of Phenols

OH OH Cl OH Br

Phenol 3-Chlorophenol

4-Bromophenol

Phenols in Medicine

Many phenols are used as antiseptics and

disinfectants. PhenolResorcinol 4-Hexylresorcinal (antiseptic) (antiseptic)OHOH OH CHquotesdbs_dbs20.pdfusesText_26

[PDF] [PDF] Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

Structure and Classification of Alcohols

14.3 Naming Alcohols, Phenols, and Thiols14.4 Some Important Alcohols and Phenols

Alcohols

In an alcohol, a

In a phenol, a

Alcohols are classified as primary, secondary, or

C - OH CH

Classification of Alcohols

A. ___CH

B. ___ CH

C. ____HO - CH

Learning Check

HO - CH

Solution

The IUPAC system replaces the -ein the

Naming Alcohols

In the IUPAC names for longer chains, the chain

OH1-propanol

2-butanol

4-methyl-2-pentanol

Naming Alcohols

2-propanol (isopropyl alcohol)

1,2-ethanediol (ethylene glycol)

1,2,3-propanetriol

Some Typical Alcohols

Name the following:

A. CH

OH CH

Learning Check

A. CH

1-butanol

OH CH

B. CH

3-methyl-2-pentanol

C.cyclopentanol

Solution

Learning Check

Write the structure of the following:

A. 3-pentanol

B. ethyl alcohol

C. 3-methylcyclohexanol

Solution

Alcohols undergo combustion with O

OH + 3O

O + Heat

Dehydrationremoves H- and -OH from adjacent

H OH

H - C - C - H H - C=C - H + H

H H H H

14.5Reactions of Alcohols

Formation of Ethers

Ethers form when dehydration takes place at low

Two Methanol Dimethyl ether

Oxidation and Reduction

In organic chemistry, oxidationis a loss of

In an oxidation, there is an increase in the

Reductionis a gain of hydrogen or a loss of

In the oxidation [O] of a primary alcohol, one H

Primary alcoholAldehyde

EthanolEthanal

Oxidation of Primary Alcohols

Secondary alcoholKetone

OHO|[O]||CH

2-PropanolPropanone(Isopropyl alcohol)(Dimethylketone; Acetone)

Oxidation of Secondary Alcohols

Tertiary alcohols are resistant to oxidation.

Tertiary alcoholsno reaction

2-Methyl-2-propanol

Oxidation of Tertiary Alcohols

OH with the following

B. [O]C. O

Learning Check

B. [O]3) CH

C. O

Solution

Is metabolized at a rate of

12-15 mg/dL per hour by a social drinker.

Is metabolized at a rate of 30

Ethanol CH