Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 5, Problem 5.36P
Interpretation Introduction

Interpretation:

Chiral carbon atoms present in nepetalactone has to be labelled. The number of possible stereoisomers for nepetalactone has to be given and to show that nepetalactone is a terpene.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Organic Chemistry, Chapter 5, Problem 5.36P , additional homework tip  1

Organic Chemistry, Chapter 5, Problem 5.36P , additional homework tip  2

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

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