Download Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones

Chapter 12
Alcohols, Phenols, Ethers,
Aldehydes, and Ketones
Oxidation and Reduction
Timberlake LesturePLUS 1999
1
Classification of Alcohols
Primary (1º)
H
Secondary (2º )
CH3
CH3-C-OH
CH3-C-OH
H
H
1 CH3
attached
to C-OH
2 CH3
attached
to
C-OH
Timberlake LesturePLUS 1999
Tertiary (3º)
CH3
CH3-C-OH
CH3
3 CH3
attached
to C-OH 2
Learning Check Ox-Red 1
Classify the following as 1º, 2º, or 3º alcohols:
OH
A. CH3CH2CH2OH
C.
OH
B. CH3-CH-CH2CH3
D.
OH
CH3-C-CH2CH3
CH3
Timberlake LesturePLUS 1999
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Solution Ox-Red 1
Classify the following as 1º, 2º, or 3º alcohols:
OH
A. CH3CH3CH2OH 1º
C.
OH
2º
B. CH3-CH-CH2CH3 2º
D.
OH
3º
CH3-C-CH2CH3
CH3
Timberlake LesturePLUS 1999
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Oxidation
Is a gain of oxygen (O)
or
A loss of hydrogen (H)
Timberlake LesturePLUS 1999
5
Alcohols
1°alcohols are oxidized to
aldehydes and 2° alcohols
are oxidized to ketones
Alcohols
1°
2°
aldehydes ketones
Timberlake LesturePLUS 1999
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Oxidation of Alcohols
[O]
Primary alcohol
OH
[O]
CH3-C-H
aldehyde
O

CH3-C-H
H
Ethanol
(ethyl alcohol)
Ethanal
(acetaldehyde)
Timberlake LesturePLUS 1999
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Oxidation of Alcohols
[O]
Secondary alcohol
OH
[O]
CH3-C-CH3
2-Propanol
(isopropyl alcohol)
ketone
O

CH3-C-CH3
2-propanone
(dimethyl ketone,
“acetone”)
Timberlake LesturePLUS 1999
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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
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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
Timberlake LesturePLUS 1999
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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
A. H+, heat
B.
2) CO2 + H2O 3) CH3CH2CH
_________
[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
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Learning Check Ox-Red 4
Write the structure of the following:
A. 3-pentanol
B. Dimethyl ether
C. 3-methylcyclobutanol
Timberlake LesturePLUS 1999
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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 CH
3
C. 3-methylcyclobutanol
Timberlake LesturePLUS 1999
OH14
Reduction
Is a loss of oxygen (O)
or
gain of hydrogen (H)
Timberlake LesturePLUS 1999
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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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