8-36 - Organic Chemistry (Mcmurry)

Question

Isolated from marine algae, prelaureatin is thought to be biosynthesized from laurediol by the following route. Propose a mechanism

Step-by-Step Solution

Answer

Mechanism of the reaction is: 

Reaction Mechanism

Reaction mechanism is a theoretical concept. It is a way of defining a reaction into simpler form. 

Electrophilic aromatic substitution

In the elementary reactions, reaction mechanism can define every step of the formation of product from the reactant in the presence of reagent, catalyst or solvent. For example: Reaction mechanism for electrophilic aromatic substitution reaction is:

                           Electrophilic aromatic substitution

Step-by-Step mechanism of reaction

Step 1: Double bond of the molecule will attack on the electrophile and will form bromonium ion.

Step 2: Lone pairs of oxygen atom will attack on carbon atom that is attached to  and formation of carbocation will take place.

Step 3: Release of proton with the help of base will take place and final product i.e. Prelaureatin will form.

                             Mechanism of the reaction