Oxidation of alcohols with copper and heat

Started by apurva, September 29, 2022, 08:59:45 AM

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apurva

Question: Reaction of Primary, Secondary and Tertiary alcohols with heated copper gives what products?

chenbeier

First copper get oxidised to copperoxide.
The hot copperoxide get reduced by the alcohol and:

Primary alcohol will be oxidised to Aldehyde and further to carbonic acid
Secundary alcohol will be oxidised to ketone
Tertiary will not affected.

Primary

R- CH2OH => R-CHO + 2H+ + 2e-
RCHO + H2O => RCOOH + 2 H+ + 2e-

Secondary

RCH2(OH)-R' => R-CO-R' + 2H+ + 2e-

2 Cu + O2 => 2  CuO Oxidation

CuO + 2 H+ + 2 e- => Cu + H2O Reduction during reaction with alcohol

In sum

R- CH2OH  + CuO => R-CHO + H2O + Cu



chenbeier

One mistake

RCH2(OH)-R' => R-CO-R' + 2H+ + 2e-
must be
RCH(OH)-R' => R-CO-R' + 2H+ + 2e-

I couldnt find a modify button

uma

#3
Quote from: chenbeier on September 29, 2022, 11:13:31 AM
First copper get oxidised to copperoxide.
The hot copperoxide get reduced by the alcohol and:

Primary alcohol will be oxidised to Aldehyde and further to carbonic acid
Secundary alcohol will be oxidised to ketone
Tertiary will not affected.

Primary

R- CH2OH => R-CHO + 2H+ + 2e-
RCHO + H2O => RCOOH + 2 H+ + 2e-

Secondary

RCH2(OH)-R' => R-CO-R' + 2H+ + 2e-

2 Cu + O2 => 2  CuO Oxidation

CuO + 2 H+ + 2 e- => Cu + H2O Reduction during reaction with alcohol

In sum

R- CH2OH  + CuO => R-CHO + H2O + Cu
Please check your answer.
Primary to aldehydes but not to carboxylic acids.
Tertiary will give alkene after dehydration.

uma

Quote from: apurva on September 29, 2022, 08:59:45 AM
Question: Reaction of Primary, Secondary and Tertiary alcohols with heated copper gives what products?
Dehydrogenation  or oxidation of alcohols using heated copper metal
When the vapours of a primary or a secondary alcohol are passed over heated copper at 573 K, dehydrogenation takes place and an aldehyde or a ketone is formed while tertiary alcohols under-go dehydration.
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