Oxidation

Overview

Full oxidation of a primary alcohol gives a carboxylic acid.

Transformation

Alcohols → Carboxylic acids

Equation

R-CH2OH + 2[O] -> R-CO2H + H2O

Reagents

acidified K2Cr2O7

Environment

heat under reflux

Reaction class

oxidation

Mechanism

oxidation

Evidence level

textbook core

Scope and limitations

Scope

Primary alcohols can be fully oxidised to carboxylic acids under reflux.

Limitations

This route records complete oxidation of primary alcohols; controlled aldehyde isolation is represented separately.

Related reactions

• Chlorination: Alcohols → Chloroalkanes

  Alcohols can be converted into chloroalkanes to create a better leaving group for downstream substitution.

• Chlorination with thionyl chloride: Alcohols → Chloroalkanes

  Thionyl chloride converts alcohols into chloroalkanes with sulfur dioxide and hydrogen chloride as by-products.

• Bromination: Alcohols → Bromoalkanes

  Bromide and acid conditions convert alcohols into bromoalkanes.

• Iodination: Alcohols → Iodoalkanes

  Iodine and red phosphorus conditions convert alcohols into iodoalkanes.

• Hydrolysis: Chloroalkanes → Alcohols

  The C-Cl bond can be displaced by hydroxide to form an alcohol.

• Hydrolysis: Bromoalkanes → Alcohols

  The C-Br bond can be displaced by hydroxide to form an alcohol.

• Hydrolysis: Iodoalkanes → Alcohols

  The C-I bond can be displaced by hydroxide to form an alcohol.

• Oxidation: Alcohols → Aldehydes

  Controlled oxidation of a primary alcohol gives an aldehyde.

• Oxidation: Alcohols → Ketones

  Oxidation of a secondary alcohol gives a ketone.

• Complete oxidation: Primary alcohols → Carboxylic acids

  Full oxidation of a primary alcohol gives a carboxylic acid.

• Reduction: Carboxylic acids → Primary alcohols

  Reduction of a carboxylic acid gives a primary alcohol.

• Oxidation: Aldehydes → Carboxylic acids

  Oxidation of an aldehyde gives a carboxylic acid.

• Hydrolysis: Nitriles → Carboxylic acids

  Nitriles can be hydrolysed to carboxylic acids, splitting the old aggregate nitrile-to-amide route into a single functional-group conversion.

• Activation for amide formation: Carboxylic acids → Amide chemistry

  Carboxylic acids or activated acid derivatives connect to amide-bond formation.

• Hydration: Alkenes → Alcohols

  Catalytic hydration converts alkenes into alcohols.

• Dehydration: Alcohols → Alkenes

  Dehydration converts alcohols into alkenes.

References

1. Pearson Edexcel Level 3 Advanced GCE in Chemistry specificationPearson Education Limited · Pearson qualifications · 2024

   Supports the textbook-core organic reaction routes used for displayed route and mechanism content.