Chapter 16, Problem 16.62P

(a)

Interpretation Introduction

Interpretation:

The given reaction is

Both compounds has to be showed as terpenes.

Concept Introduction:

Terpene:

The compounds which contains two or more isoprene units in their structure are said to be terpenes.

Isoprene (2-methyl-1,3-butadiene) unit is a molecule with five carbon atoms with double bonds.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the conversion of (S)-Citronellal to Isopulegol has to be proposed.

(c)

Interpretation Introduction

Interpretation:

In Isopulegol, the number of stereocenters present has to be given and the number of stereoisomers possible for a molecule with this number of stereocenters has to be given.

Concept Introduction:

A carbon which is bonded to four different groups is said to be chiral carbon.  A chiral carbon in a molecule is said to be chiral center.  All chiral centers are stereocenters.

(d)

Interpretation Introduction

Interpretation:

Isopulegol is formed as a single stereoisomer.  The fact that only single stereoisomer is formed has to be accounted.