Chapter 12

Alcohols, Phenols, Ethers,

Aldehydes, and Ketones

Oxidation and Reduction

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 Classification of Alcohols
Primary (1º) Secondary (2º ) Tertiary (3º)

H CH3 CH3

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

H H CH 3

1 CH3 2 CH3 3 CH3

attached attached
Timberlake LesturePLUS 1999
attached 2
to C-OH to C-OH to C-OH
 Learning Check Ox-Red 1

Classify the following as 1º, 2º, or 3º alcohols:

OH

A. CH3CH2CH2OH B. CH3-CH-CH2CH3

OH
C. D. OH

CH3-C-CH2CH3

CH3
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 Solution Ox-Red 1

Classify the following as 1º, 2º, or 3º alcohols:

OH

A. CH3CH3CH2OH 1º B. CH3-CH-CH2CH3 2º
OH
C. 2º D. OH 3º

CH3-C-CH2CH3

CH3
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 Oxidation

Is a gain of oxygen (O)

or

A loss of hydrogen (H)

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 Alcohols

1°alcohols are oxidized to

aldehydes and 2° alcohols are
oxidized to ketones
Alcohols
1° 2°
aldehydes ketones
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 Oxidation of Alcohols
[O]
Primary alcohol aldehyde
OH O
[O] 
CH3-C-H CH3-C-H

H
Ethanol Ethanal
(ethyl alcohol) (acetaldehyde)
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 Oxidation of Alcohols
[O]
Secondary alcohol ketone
OH O
[O] 
CH3-C-CH3 CH3-C-CH3

2-Propanol 2-propanone
(isopropyl alcohol) (dimethyl ketone,
“acetone”)
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 Oxidation of Alcohols
[O]
Tertiary alcohols no reaction
OH [O]

CH3-C-CH3 no product

CH3 no H on the C-OH to oxidize

2-Methyl-2-propanol
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 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 CH3CH CH3COH 2CO2 + H2O
ethyl alcohol acetaldhyde acetic acid

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 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] _________
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C. O , heat _________
 Solution Ox-Red 3
Select the product for the reaction of
CH3CH2CH2OH in the following conditions:

A. H+, heat 1) CH3CH=CH2

O

B. [O] 3) CH3CH2CH

C. O2, heat 2) CO2 + H2O

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 Learning Check Ox-Red 4
Write the structure of the following:
A. 3-pentanol

B. Dimethyl ether

C. 3-methylcyclobutanol

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 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 OH14
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 Reduction

Is a loss of oxygen (O)

or

gain of hydrogen (H)

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 Reduction

Aldehydes are reduced to 1°

alcohols and ketones are
reduced to 2° alcohols
Alcohols
1° 2°
aldehydes ketones
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