Octet

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Cannizzaro Reaction

Cannizzaro Reaction (Oxidation.) Converts c1ccccc1C=O to c1ccccc1CO.c1ccccc1C(=O)[O-] using NaOH (conc.), KOH. Conditions: Strong base, no α-hydrogens.

Oxidation

Reaction details

Name

Cannizzaro Reaction

Type

Oxidation

Starting Material

c1ccccc1C=O

Product

c1ccccc1CO.c1ccccc1C(=O)[O-]

Reagents

  • NaOH (conc.)

  • KOH

Conditions

Strong base, no α-hydrogens

Mechanism
  1. Smiles

    c1ccccc1C=O

    Description

    Benzaldehyde: no α-hydrogens (cannot enolize)

  2. Smiles

    c1ccccc1C=O

    Description

    OH⁻ attacks carbonyl, hydride transfers to another aldehyde

  3. Smiles

    c1ccccc1CO.c1ccccc1C(=O)[O-]

    Description

    One molecule oxidized (acid), one reduced (alcohol)

Tips

  1. Disproportionation: 2 aldehydes → 1 alcohol + 1 carboxylate

  2. Only for aldehydes WITHOUT α-hydrogens

  3. With α-H, aldol reaction occurs instead

  4. Formaldehyde + other aldehyde = crossed Cannizzaro

Related Reactions

  • aldol-addition

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Reactions

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Source collection

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution.) Converts CCBr to CCO using NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion).

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed..

Elimination

Study guides

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