Octet

Octet / Reactions

Mitsunobu Reaction

Mitsunobu Reaction (Substitution.) Converts CC(C)O to CC(C)N3 using DEAD or DIAD, PPh₃, Nucleophile (pKa < 15). Stereochemistry: Inversion of configuration (like SN2).

Substitution

Reaction details

Name

Mitsunobu Reaction

Type

Substitution

Starting Material

CC(C)O

Product

CC(C)N3

Reagents

  • DEAD or DIAD

  • PPh₃

  • Nucleophile (pKa < 15)

Mechanism
  1. Smiles

    CC(C)O

    Description

    Secondary alcohol

  2. Smiles

    CC(C)O

    Description

    PPh₃ + DEAD activate alcohol

  3. Smiles

    CC(C)N3

    Description

    Nucleophile displaces with INVERSION

Stereochemistry

Inversion of configuration (like SN2)

Tips

  1. Converts alcohol to other groups with INVERSION

  2. Nucleophiles: azides, phthalimide, carboxylic acids, phenols

  3. pKa of nucleophile must be < 15

  4. Great for stereochemistry manipulation

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

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

Related study guides

Free, in-depth guides that put this material in context.

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