Preparing Esters - ethyl 2-butenoate preparation from ethanol

Derive ethyl 2-butenoate from ethanol using following reagents

PCC , dil.NaOH , H2O2 , PCl3


PROBLEM

ethanol to ethyl 2-butenoate conversion

Little tips to do the problem


Ethanol and PCC reaction

Alcohol reacts with PCC to give aldehydes. Therefore ethanol reacts with PCC to give ethanal.

Aldehydes and hydrogen peroxide reaction

Aldehydes are oxidized to carboxylic acid by hydrogen peroxide reaction. Hydrogen peroxide is a mild oxidizing agent. Alkenes are not oxidized by hydrogen peroxide.

  • ethyl but-2-enoate compound is an ester. Ester can be produced by adding ethanol to relevant acid chlorides.
  • Acid chlorides can be formed by carboxylic acids.
  • carbon chain can be extended by aldol reaction. ( aldehydes and NaOH/KOH reaction ). In this reaction number of carbon atoms are doubled

SOLUTION

ethanol to ethyl 2-butenoate conversion




Lewis structures

P2O5 lewis structure OH- lewis structure Ammonium ion (NH4+) lewis structure H2CO3 lewis structure