Transcript Alcohols - Organic Chemistry

Alcohols – Phenols - Ethers
Oxidation and Reduction
Timberlake LesturePLUS 1999
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Classification of Alcohols
Primary (1º)
(3º)
H
CH3-C-OH
H
1 CH3
attached
to C-OH
Secondary (2º )
CH3
Tertiary
CH3
CH3-C-OH
H
2 CH3
attached
to C-OH
CH3-C-OH
CH3
3 CH3
attached
to C-OH
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Learning Check Ox-Red 1
Classify the following as 1º, 2º, or 3º alcohols:
OH
A. CH3CH2CH2OH
C.
B. CH3-CH-CH2CH3
D.
OH
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. CH3CH2CH2OH 1º
C.
OH
B. CH3-CH-CH2CH3 2º
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
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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
OH
[O]
CH3-C-H
aldehyde
O

CH3-C-H
H
Ethanol
(ethyl alcohol)
Ethanal
(acetaldehyde)
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Oxidation of Alcohols
[O]
Secondary alcohol
OH
CH3-C-CH3
2-Propanol
alcohol)
ketone
O
[O]

CH3-C-CH3
2-propanone (isopropyl
(dimethyl ketone,
“acetone”)
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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
[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
2) CO2 + H2O 3) CH3CH2CH
_________
B. [O]
_________
C. O2, heat
_________
Timberlake LesturePLUS 1999
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Solution Ox-Red 3
Select the product for the reaction of CH3CH2CH2OH in
the following conditions:
A. H+, heat
B. [O]
1) CH3CH=CH2
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
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
CH3
C. 3-methylcyclobutanol
OH
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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°
aldehydes
2°
ketones
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