Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 27.SE, Problem 29AP
Interpretation Introduction

a)

Organic Chemistry, Chapter 27.SE, Problem 29AP , additional homework tip  1

Interpretation:

At what positions the terpenoid guaiol will be labeled if isopentyl diphosphate and dimethylallyl diphosphate from which they are synthesized are isotopically labeled at the diphosphate bearing carbon atom (C1).

Concept introduction:

In the formation of terpenes every fourth carbon of one dimethylallyl phosphate (formed by the isomerization of isopentyl diphosphate) combines with the first carbon of the isopentyl phosphate molecule. Hence if the diphosphate bearing carbon is labeled, every fourth carbon in a terpene will be a labeled carbon.

To give:

The positions at which the terpenoid guaiol will be labeled if isopentyl diphosphate and dimethylallyl diphosphate from which it is synthesized are isotopically labeled at the diphosphate bearing carbon atom (C1).

Interpretation Introduction

b)

Organic Chemistry, Chapter 27.SE, Problem 29AP , additional homework tip  2

Interpretation:

At what positions the terpenoid sabinene will be labeled if isopentyl diphosphate and dimethylallyl diphosphate from which they are synthesized are isotopically labeled at the diphosphate bearing carbon atom (C1).

Concept introduction:

In the formation of terpenes every fourth carbon of one dimethylallyl phosphate (formed by the isomerization of isopentyl diphosphate) combines with the first carbon of the isopentyl phosphate molecule. Hence if the diphosphate bearing carbon is labeled, every fourth carbon in a terpene will be a labeled carbon.

To give:

The positions at which the terpenoid sabinene will be labeled if isopentyl diphosphate and dimethylallyl diphosphate from which it is synthesized are isotopically labeled at the diphosphate bearing carbon atom (C1).

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Chapter 27 Solutions

Organic Chemistry

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