Octet

Octet / Reactions

Acid-Catalyzed Ester Hydrolysis

Acid-Catalyzed Ester Hydrolysis (Carbonyl.) Converts CC(=O)OCC to CC(=O)O.CCO using H₂O, H₂SO₄ or HCl. Conditions: Aqueous acid, reflux.

Carbonyl

Reaction details

Name

Acid-Catalyzed Ester Hydrolysis

Type

Carbonyl

Starting Material

CC(=O)OCC

Product

CC(=O)O.CCO

Reagents

  • H₂O

  • H₂SO₄ or HCl

Conditions

Aqueous acid, reflux

Mechanism
  1. Smiles

    CC(=O)OCC

    Description

    Ethyl acetate (ester)

  2. Smiles

    CC(=O)OCC

    Description

    Protonation of carbonyl O activates for attack

  3. Smiles

    CC(=O)O.CCO

    Description

    Water attacks, alcohol leaves → acetic acid + ethanol

Tips

  1. Reversible! (reverse of Fischer esterification)

  2. Use excess water to drive equilibrium

  3. Acid protonates carbonyl oxygen

  4. AAC2 mechanism

Related Reactions

  • fischer-esterification

  • ester-hydrolysis-base

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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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