Chapter 12

Alcohols, Phenols, Ethers,

Aldehydes, and Ketones
Oxidation and Reduction

Timberlake LesturePLUS 1999

Classification of Alcohols
Primary (1)
H

Secondary (2 ) Tertiary (3)

CH3

CH3

CH3-C-OH CH3-C-OH CH3-C-OH

H
1 CH3
attached
to C-OH

H
2 CH3
attached
to C-OH

3 CH3
attached
to C-OH

Timberlake LesturePLUS 1999

CH 3

Learning Check Ox-Red 1

Classify the following as 1, 2, or 3 alcohols:
OH
A. CH3CH2CH2OH
C.

D.

B. CH3-CH-CH2CH3

OHOH

CH3-C-CH2CH3
CH3

Timberlake LesturePLUS 1999

Solution Ox-Red 1
Classify the following as 1, 2, or 3 alcohols:
OH
A. CH3CH3CH2OH 1
C.

D.
OH

OH

B. CH3-CH-CH2CH3 2
3

CH3-C-CH2CH3
CH3

Timberlake LesturePLUS 1999

Oxidation

Is a gain of oxygen (O)

or

A loss of hydrogen (H)

Timberlake LesturePLUS 1999

Alcohols
1alcohols are oxidized to
aldehydes and 2 alcohols
are oxidized to ketones
Alcohols
1
2
aldehydes ketones
Timberlake LesturePLUS 1999

Oxidation of Alcohols
[O]
Primary alcohol
OH
CH3-C-H

aldehyde
[O]

CH3-C-H

H
Ethanol
(ethyl alcohol)

Ethanal
(acetaldehyde)

Timberlake LesturePLUS 1999

Oxidation of Alcohols
[O]
Secondary alcohol
OH
CH3-C-CH3
2-Propanol
(isopropyl alcohol)

[O]

ketone
O

CH3-C-CH3
2-propanone
(dimethyl ketone,
acetone)

Timberlake LesturePLUS 1999

Oxidation of Alcohols
[O]
Tertiary alcohols
OH

no reaction
[O]

CH3-C-CH3
CH3

no product
no H on the C-OH to oxidize

2-Methyl-2-propanol
Timberlake LesturePLUS 1999

Oxidation of Ethanol in the

Body
Enzymes in the liver oxidize ethanol
Aldehyde product impairs coordination
Blood alcohol over 0.4% can be fatal.
O
O

CH3CH2OH
ethyl alcohol

CH3CH

CH3COH

2CO2 + H2O

acetaldhyde acetic acid

Timberlake LesturePLUS 1999

10

Learning Check Ox-Red 3

Select the product for the reaction of
CH3CH2CH2OH in the following conditions:
O

1) CH3CH=CH2

2) CO2 + H2O 3) CH3CH2CH

A. H+, heat

_________

B.

_________

[O]

C. O2, heat

_________

Timberlake LesturePLUS 1999

11

Solution Ox-Red 3
Select the product for the reaction of
CH3CH2CH2OH in the following conditions:
A. H+, heat

B.

[O]

C. O2, heat

1) CH3CH=CH2
O

3) CH3CH2CH
2) CO2 + H2O
Timberlake LesturePLUS 1999

12

Learning Check Ox-Red 4

Write the structure of the following:
A. 3-pentanol
B. Dimethyl ether
C. 3-methylcyclobutanol

Timberlake LesturePLUS 1999

13

Solution Ox-Red 4
Write the structure of the following:
OH
|
A. 3-pentanol

CH3CH2CHCH2CH3

B. Dimethyl ether

CH3-O-CH3 CH3

C. 3-methylcyclobutanol
Timberlake LesturePLUS 1999

OH14

Reduction

Is a loss of oxygen (O)

or

gain of hydrogen (H)

Timberlake LesturePLUS 1999

15

Reduction
Aldehydes are reduced to 1
alcohols and ketones are
reduced to 2 alcohols
Alcohols
1
aldehydes

2
ketones

Timberlake LesturePLUS 1999

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