1. Oxidation and Reduction
Chapter 14 Alcohols, Phenols, Ethers (and begin Aldehydes, and Ketones)
Oxidation and Reduction
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2. Classification of Alcohols
Primary (1º) Secondary (2º ) Tertiary (3º)
H CH CH3
CH3-C-OH CH3-C-OH CH3-C-OH
H H CH3
1 CH CH3 3 CH3
attached attached attached
to C-OH to C-OH to C-OH
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3. Learning Check Ox-Red 1
Classify the following as 1º, 2º, or 3º alcohols: OH
A. CH3CH2CH2OH B. CH3-CH-CH2CH3
C D OH
CH3-C-CH2CH3
CH3
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4. Solution Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH
A. CH3CH2CH2OH 1º B. CH3-CH-CH2CH3 2º
C º D OH º
CH3-C-CH2CH3
CH3
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5. Oxidation (OIL or LEO) Is a gain of oxygen (O) or
A loss of hydrogen (H)
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6. Alcohols Alcohols aldehydes ketones
1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones
Alcohols
1° °
aldehydes ketones
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7. 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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8. Oxidation of Alcohols [O] Secondary alcohol ketone OH O [O] 
CH3-C-CH CH3-C-CH3
2-Propanol 2-propanone (isopropyl alcohol) (dimethyl ketone, “acetone”)
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9. Oxidation of Alcohols [O] Tertiary alcohols no reaction OH [O]
CH3-C-CH3 no product
CH no H on the C-OH to oxidize
2-Methyl-2-propanol
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10. 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 CO2 + H2O
ethyl alcohol acetaldhyde acetic acid
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11. Learning Check Ox-Red 3
Select the product for the reaction of CH3CH2CH2OH in the following conditions:
O 
1) CH3CH=CH ) CO2 + H2O 3) CH3CH2CH
A. [O] _________
B. O2, heat _________
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12. Solution Ox-Red 3
Select the product for the reaction of CH3CH2CH2OH in the following conditions: O 
A. [O] 3) CH3CH2CH
B. O2, heat 2) CO2 + H2O
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13. Learning Check Ox-Red 4 Write the structure of the following:
A. 3-pentanol
B. Dimethyl ether
C. 3-methylcyclobutanol
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14. Solution Ox-Red 4 Write the structure of the following: OH |
A. 3-pentanol CH3CH2CHCH2CH3
B. Dimethyl ether CH3-O-CH3
C. 3-methylcyclobutanol
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15. Reduction
Is a loss of oxygen (O) or
gain of hydrogen (H)
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16. Reduction
Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols
Alcohols
1° 2°
aldehydes ketones
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