Oxidation of Alcohols

In this video we want to discuss the oxidation of alcohols.

Interestingly the extent of oxidation of primary, secondary and tertiary alcohols are different to form different products.

1. Oxidation of Primary Alcohol

The overview of the oxidation of primary alcohols and reduction of aldehydes and carboxylic acids to form primary alcohols is as shown.

oxidation of alcohols oxidation of primary alcohols overview

There are 5 reactions in total.

a. Controlled oxidation of primary alcohol to aldehyde via K2Cr2O7 in dilute H2SO4, reflux with immediate distillation

oxidation of alcohols oxidation of primary alcohol to aldehyde

b. Oxidation of aldehyde to carboxylic acid via KMnO4 or K2Cr2O7 in dilute H2SO4, heat or reflux.

oxidation of alcohols oxidation of aldehyde to acid

c. Oxidation of primary alcohol to carboxylic acid via KMnO4 or K2Cr2O7 in dilute H2SO4, heat or reflux.

oxidation of alcohols oxidation of primary alcohol to acid

d. Reduction of aldehyde to primary alcohol via NaBH4(aq) at room temperature, or LiAlH4 in dry ether followed by water at room temperature, or H2(g) in Pt catalyst, heat.

oxidation of alcohols reduction of aldehyde to primary alcohol

e. Reduction of carboxylic acid to primary alcohol via LiAlH4 in dry ether followed by water at room temperature.

oxidation of alcohols reduction of acid to primary alcohol

2. Oxidation of Secondary Alcohol

Secondary alcohol can be oxidised to ketone via KMnO4 or K2Cr2O7 in dilute H2SO4, heat or reflux.

Conversely ketone can be reduced to secondary alcohol via NaBH4(aq) at room temperature, or LiAlH4 in dry ether followed by water at room temperature, or H2(g) in Pt catalyst, heat.

oxidation of alcohols oxidation of secondary alcohol to ketone

3. Oxidation of Tertiary Alcohol

Tertiary alcohols are resistant to oxidation as the alcohol carbon has no hydrogen to lose, hence cannot be oxidised.

oxidation of alcohols oxidation of tertiary alcohols

For the detailed discussion of oxidation of primary alcohols, secondary alcohols and tertiary alcohols, and the reduction of carbonyl compounds and carboxylic acids to form alcohols, check out this video!

It's also important to know how to determine the oxidation state of carbon in organic compounds.

Topic: Alcohols, Organic Chemistry, A Level Chemistry, Singapore

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