Octet

Octet / Reactions

Reformatsky Reaction

Reformatsky Reaction (Addition.) Converts BrCC(=O)OCC to CC(O)CC(=O)OCC using α-Bromo ester, Zn, aldehyde or ketone.

Addition

Reaction details

Name

Reformatsky Reaction

Type

Addition

Starting Material

BrCC(=O)OCC

Product

CC(O)CC(=O)OCC

Reagents

  • α-Bromo ester

  • Zn

  • aldehyde or ketone

Mechanism
  1. Smiles

    BrCC(=O)OCC

    Description

    Ethyl bromoacetate

  2. Smiles

    [Zn]CC(=O)OCC

    Description

    Organozinc forms (like Grignard but less reactive)

  3. Smiles

    CC(O)CC(=O)OCC

    Description

    β-Hydroxy ester after addition to carbonyl

Tips

  1. Like Grignard but for α-bromo esters

  2. Zn less reactive than Mg - ester survives

  3. Product: β-hydroxy ester

  4. Useful when Grignard would attack the ester

Related Reactions

  • grignard-addition

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Reactions

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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

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