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Strecker Synthesis

Strecker Synthesis (Addition.) Converts CC=O to CC(N)C(=O)O using NH₃, HCN, then H₃O⁺.

Addition

Reaction details

Name

Strecker Synthesis

Type

Addition

Starting Material

CC=O

Product

CC(N)C(=O)O

Reagents
  • NH₃

  • HCN

  • then H₃O⁺

Mechanism
  1. Smiles

    CC=O

    Description

    Aldehyde

  2. Smiles

    CC=N

    Description

    Imine forms with ammonia

  3. Smiles

    CC(N)C#N

    Description

    Cyanide adds to give α-aminonitrile

  4. Smiles

    CC(N)C(=O)O

    Description

    Hydrolysis of nitrile gives α-amino acid

Tips
  1. Classic amino acid synthesis

  2. Aldehyde → α-Amino acid

  3. Racemic product (non-stereoselective)

  4. One of oldest named reactions (1850)

Related Reactions
  • gabriel-synthesis

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