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

Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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