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Aldol Addition

Aldol Addition (Carbonyl.) Converts CC=O to CC(O)CC=O using NaOH (dilute), LDA. Conditions: Low temperature for addition (warm for condensation).

Carbonyl

Reaction details

Name

Aldol Addition

Type

Carbonyl

Starting Material

CC=O

Product

CC(O)CC=O

Reagents
  • NaOH (dilute)

  • LDA

Conditions

Low temperature for addition (warm for condensation)

Mechanism
  1. Smiles

    CC=O

    Description

    Acetaldehyde

  2. Smiles

    CC=O

    Description

    Base removes α-H, forming enolate

  3. Smiles

    CC(O)CC=O

    Description

    Enolate attacks another aldehyde → β-hydroxy aldehyde

Tips
  1. Aldol = aldehyde + alcohol (functional groups in product)

  2. With heat: dehydration gives α,β-unsaturated carbonyl

  3. Crossed aldol needs careful control

Related Reactions
  • aldol-condensation

  • claisen-condensation

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