Octet

Octet / Reactions

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

Reaction details

Name

SN2 with Cyanide

Type

Substitution

Subtype

SN2

Starting Material

CCI

Product

CC#N

Reagents

  • NaCN

  • KCN

Conditions

Polar aprotic solvent

Solvent

DMSO or DMF

Mechanism
  1. Smiles

    CCI

    Description

    Iodoethane: I is excellent leaving group

  2. Smiles

    CCI

    Description

    Cyanide (strong nucleophile) attacks from backside

  3. Smiles

    CC#N

    Description

    Propionitrile formed, I⁻ leaves

Stereochemistry

Inversion of configuration

Tips

  1. Cyanide is a great nucleophile for adding one carbon

  2. Product nitrile can be hydrolyzed to carboxylic acid or reduced to amine

  3. Iodide is best leaving group (most polarizable)

Related Reactions

  • sn2-bromide-hydroxide

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

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

E1 Elimination

E1 Elimination (E1 Elimination.) Converts CC(C)(C)Br to CC(C)=C using Weak base or heat. Conditions: Polar protic solvent, heat in Water or alcohol. Stereochemistry: No stereospecificity (unlike E2).

Elimination

Study guides

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Arrow-pushing basicsSN1 vs SN2 decision guideStudy reactions without memorizingAll guides