Octet

Octet / Reactions

Gabriel Synthesis

Gabriel Synthesis (Substitution.) Converts O=C1c2ccccc2C(=O)N1 to CCN using R-X (1° alkyl halide), then N₂H₄ or NaOH/heat.

Substitution

Reaction details

Name

Gabriel Synthesis

Type

Substitution

Starting Material

O=C1c2ccccc2C(=O)N1

Product

CCN

Reagents

  • R-X (1° alkyl halide)

  • then N₂H₄ or NaOH/heat

Mechanism
  1. Smiles

    O=C1c2ccccc2C(=O)N1

    Description

    Potassium phthalimide (phthalimide + KOH)

  2. Smiles

    O=C1c2ccccc2C(=O)N1CC

    Description

    SN2 with alkyl halide

  3. Smiles

    CCN

    Description

    Hydrazine cleaves to release 1° amine

Tips

  1. Makes pure PRIMARY amines (no over-alkylation)

  2. Only works with 1° (and some 2°) halides (SN2)

  3. Alternative to direct alkylation of ammonia

  4. Hydrazine releases amine, forms phthalhydrazide

Related Reactions

  • sn2-azide

This is one row of the Reaction roadmap sheet - print all 83 reactions on one page.

Reactions

Related Content

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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