Question

Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

(d)

Short answer

Answer

The product of the reaction is:

Step-by-step solution

Oxymercuration / Demercuration of alkenes

It is an example of electrophilic addition reaction. In this reaction, an alkene is converted into neutral alcohol.

HgOAC2, H2O 2. NABH4 Reagent

When alkene is treated with the reagent ($Hg{\left(OAC\right)}_2,H_{2}O2.NAB{H}_4$) the product will be alcohol and this reaction is known as oxymercuration- demercuration reaction. Through this reaction, we can easily do the addition of water without the use of any acidic conditions. In this reaction, in the presence of reagent mercury (II) acetate cyclic mercurinium ion will form and this is known as oxymercuration reaction.After that reagent will do reduction and this reaction is known as the demercuration reaction. Collectively this is known as oxymercuration- demercuration reaction.

Product of reaction

Mercury(II) acetate has an empty d- orbitals therefore, it will act as an electrophile and as alkene contains a double bond that will act as a nucleophile therefore, will form cyclic mercurinium ion and Hg-OAC will release then in the presence of water hydroxide ion will attach on most substituted carbon. After that in the presence of reagent$NaB{H}_4$ reduction will take place and carbon– mercury bond will reduce. This reaction will follow Markovnikov’s rule. Hence, the product of the reaction is: