Woodward Reaction

Table of Contents

What is Woodward Reaction?

Woodward Hydroxylation is the synthesis of syn-diols or cis-diols from alkenes. This reaction is named after an American organic chemist, Robert Burns Woodward. When alkene is treated with iodine and silver acetate, it will undergo nucleophilic displacement with acetate in the presence of water. The intermediate product gives the desired diols on hydrolysis.

Woodward reaction of an anion with a double bond may be regarded as close to an SN2 displacement – one of the two bonds of that double bond being displaced, by backside attack with the stereochemistry that is hard in certain cases.

Woodward Reaction 01

The reaction is cis-hydroxylation of an alkene and is known as Woodward cis-hydroxylation, after the name of its discoverer R.B. Woodward.

Recommended Videos

Hydrolysis

Woodward Reaction Mechanism

The Woodward reaction allows the synthesis of syn-diols from alkenes by the addition of iodine followed by nucleophilic displacement with acetate in the presence of water. Hydrolysis of the intermediate ester gives the desired diol.

The steps involved in the mechanism of the Woodward reaction are listed below.

  1. Iodine reacts with alkene forming a cyclic iodonium intermediate.
  2. Further, the cyclic intermediate reacts with acetate ion in an SN2 fashion to form a five-membered ring compound.
  3. The five-membered rings are opened by a Hydrolysis reaction.
  4. Further protonation followed by hydrolysis gives the corresponding diols.

Woodward Reaction 02

Frequently Asked Questions – FAQs

Q1

What is Woodward reaction?

The Woodward reaction allows the synthesis of syn-diols from alkenes by the addition of iodine followed by nucleophilic displacement with acetate in the presence of water. Hydrolysis of the intermediate ester gives the desired diol.
Q2

What is Woodward reagent?

A solution of iodine and silver acetate or silver benzoate (in equimolar amount) in moist acetic acid is known as the Woodward reagent.
Q3

Which reagent is used for Woodward hydroxylation?

Woodward cis-Hydroxylation. The Woodward Reaction allows the synthesis of syn-diols from alkenes by the addition of iodine followed by nucleophilic displacement with acetate in the presence of water.
Q4

What is a hydroxylation reaction?

Hydroxylation is an oxidation reaction in which the carbon-hydrogen (C-H) bond oxidizes into a carbon–hydroxyl (C-OH) bond.
Test Your Knowledge On Woodward Reaction!