Question

Show the structure of A, B, C and D in the following reaction scheme:

Answer 1

Compound A is an optically active alkene. It contains one carbon-carbon double bond and one chiral carbon atom. It is 3-methyl-1-pentene. In presence of sulphuric acid, it adds a molecule of water to form compound D which is 3-methyl-3-pentanol. -OH group is added to a tertiary carbon atom as the tertiary carbocation is most stable. It is optically inactive.
Hydrogenation of compound A in presence of Pt gives compound B (3-methyl pentane) which is optically inactive. A molecule of hydrogen is added across carbon carbon double bond.
Oxymercuration demercuration of compound A gives optically active compound C which is 3-methyl -2-pentanol. A molecule of water is added across carbon carbon double bond.