Octet

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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

Reaction details

Name

SN1 Solvolysis

Type

Substitution

Subtype

SN1

Starting Material

CC(C)(C)Br

Product

CC(C)(C)O

Reagents

  • H₂O

Conditions

Polar protic solvent, heat

Solvent

Water or aqueous ethanol

Mechanism
  1. Smiles

    CC(C)(C)Br

    Description

    Tertiary bromide: bulky, SN2 impossible

  2. Smiles

    CC(C)(C)Br

    Description

    Rate-determining step: C-Br bond breaks, Br⁻ leaves

  3. Smiles

    C[C+](C)C

    Description

    Carbocation intermediate forms (planar, sp²)

  4. Smiles

    CC(C)(C)O

    Description

    Water attacks planar carbocation from either face

Stereochemistry

Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)

Tips

  1. Rate = k[substrate] - unimolecular (nucleophile not in rate law)

  2. Works best with 3° substrates, OK with 2°, fails with 1°

  3. Carbocation stability: 3° > 2° > 1° > methyl

  4. Watch for carbocation rearrangements!

  5. Chiral substrates give racemic products (or partial racemization)

Related Reactions

  • sn2-bromide-hydroxide

  • e1-elimination

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

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

Related study guides

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