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Aldehydes and Ketones

The carbonyl functional group is a carbon double bonded to an oxygen atom. It is present in aldehydes, ketones, carboxylic acids, and amides.

Redox behaviour

Redox behaviour

  • Aldehydes can be oxidised to carboxylic acids or reduced to primary alcohols.
  • Ketones cannot be oxidised but can be reduced to a secondary alcohol.
Identifying aldehydes and ketones

Identifying aldehydes and ketones

  • There are three tests: Benedict’s solution, Fehling’s solution, or Tollen’s reagent.
    • Benedict’s and Fehling’s solution will turn from blue to brick red in the presence of an aldehyde, but do nothing with a ketone.
    • Tollen’s reagent will coat the test-tube in a silver mirror in the presence of an aldehyde, but stay clear with a ketone.

Carbonyls and Reduction

Carbonyls can be reduced to alcohols.

Hydride reduction

Hydride reduction

  • The mechanism for the reduction of an aldehyde by a hydride ion is shown.
    • Note how the H is acting as a nucleophile as it attacks the carbonyl.
  • The mechanism is called a nucleophilic addition reaction.
    • It is used here to reduce aldehydes and ketones to primary and secondary alcohols.
Sodium borohydride

Sodium borohydride

  • We get the H from NaBH4 - sodium borohydride.
    • It is called a hydride source.

Key points

  • You can’t have a free hydride ion - it’s too reactive.
    • The reactive ion is actually the B-H bond, but you can draw it as a H- ion in mechanisms.
  • NaBH4 will only reduce carbonyls once because the alcohol is less reactive. The reasons for that are complex!
Jump to other topics
1

Physical Chemistry

1.1

Atoms, Molecules & Stoichiometry

1.2

Atomic Structure

1.3

Chemical Bonding

1.4

States of Matter

1.5

Chemical Energetics

1.6

Electrochemistry

1.7

Equilibria

1.8

Partition Coefficient

1.9

Reaction Kinetics

2

Inorganic Chemistry

3

Organic Chemistry & Analysis

3.1

Introduction to Organic Chemistry

3.2

Hydrocarbons

3.3

Halogen Derivatives

3.4

Hydroxy Compounds

3.5

Carbonyl Compounds

3.6

Carboxylic Acids & Derivatives

3.7

Nitrogen Compounds

3.8

Polymerisation

3.9

Analytical Techniques

3.10

Organic Synthesis

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