Octet

Octet / Reactions

Malonic Ester Synthesis

Malonic Ester Synthesis (Substitution.) Converts CCOC(=O)CC(=O)OCC to CCC(=O)O using NaOEt, R-X, then H₃O⁺/heat.

Substitution

Reaction details

Name

Malonic Ester Synthesis

Type

Substitution

Starting Material

CCOC(=O)CC(=O)OCC

Product

CCC(=O)O

Reagents

  • NaOEt

  • R-X

  • then H₃O⁺/heat

Mechanism
  1. Smiles

    CCOC(=O)CC(=O)OCC

    Description

    Diethyl malonate: acidic α-H (pKa ~13)

  2. Smiles

    CCOC(=O)C([C-])C(=O)OCC

    Description

    Deprotonation gives stabilized enolate

  3. Smiles

    CCC(=O)O

    Description

    After alkylation, hydrolysis, and decarboxylation → carboxylic acid

Tips

  1. Makes substituted acetic acids

  2. Can alkylate twice for disubstituted

  3. Decarboxylation: β-keto acid loses CO₂

  4. Partner: acetoacetic ester synthesis (makes ketones)

Related Reactions

  • acetoacetic-ester-synthesis

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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

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