Octet

Octet / Reactions

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

Reaction details

Name

SN2 with Tosylate Leaving Group

Type

Substitution

Subtype

SN2

Starting Material

CCOS(=O)(=O)c1ccc(C)cc1

Product

CCN=[N+]=[N-]

Reagents

  • NaN₃

Conditions

Polar aprotic solvent

Mechanism
  1. Smiles

    CCOS(=O)(=O)c1ccc(C)cc1

    Description

    Ethyl tosylate: OTs is excellent leaving group

  2. Smiles

    CCN=[N+]=[N-]

    Description

    Azide attacks from backside, tosylate leaves

Tips

  1. Tosylates made from alcohols: ROH + TsCl → ROTs

  2. Converts poor leaving group (OH) to great one (OTs)

  3. OTs leaving group ability similar to Br⁻

  4. Azide can be reduced to amine (LiAlH₄ or H₂/Pd)

Related Reactions

  • sn2-bromide-hydroxide

  • 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 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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