Bw Copy Oxidation

Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Oxidation and Reduction

Timberlake LesturePLUS 1999

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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 Timberlake LesturePLUS 1999 to C-OH

Tertiary (3º) CH3 CH3-C-OH CH 3 3 CH3 attached 2 to C-OH

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

B. CH3-CH-CH2CH3 2º

OH C.

2º

D.

OH

3º

CH3-C-CH2CH3 Timberlake LesturePLUS 1999

CH3

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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 Timberlake LesturePLUS 1999

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

aldehyde [O]

O  CH3-C-H

H Ethanol (ethyl alcohol)

Ethanal (acetaldehyde)

Timberlake LesturePLUS 1999

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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

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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 ethyl alcohol

CH3CH

CH3COH

2CO2 + H2O

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

2) CO2 + H2O 3) CH3CH2CH

A. H+, heat

_________

B.

_________

[O]

C. O , 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]

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 CH3

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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