Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393663549
Author: KARTY, Joel
Publisher: W. W. Norton and Company
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Chapter 11, Problem 11.48P
Interpretation Introduction

Interpretation:

The mechanism for the biosynthesis of α-pinene from geranyl pyrophosphate is to be drawn.

Concept introduction:

Many natural products like essential oils and steroids are terpenes or terpenoids. These contain a carbon backbone made up of isoprene units linked by the terminal carbons. An isoprene unit has the same carbon backbone as 2-methylbutane. The synthesis of many termpenes starts with an isoprene unit attached to a pyrophosphate ion. Addition of another isoprene unit gives the ten carbon geranyl pyrophosphate. This can react in a number of ways to produce different termpenes.

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a. What is the eluent used in the column chromatography here (a “silica plug filtration” is essentially a very short column)? b. The spectroscopy of compound 5b is described in the second half of this excerpt, including 1H-NMR and 13C-NMR (which you will learn about in CHEM 2412L), MS (which you will learn about later in CHEM 2411L) and IR. One of the IR signals is at 3530 cm-1. What functional group does this indicate might be present in compound 5b?
Steps and explanations. Also provide, if possible, ways to adress this kind of problems in general.
a. The first three lines of this procedure describe the reaction used to make compound 5b. In the fourth line, hexane and sodium bicarbonate are added. What organic lab technique is being used here?  b. What is the purpose of the Na2SO4?  c. What equipment would you use to “concentrate [a solution] under reduced pressure”?

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Organic Chemistry: Principles And Mechanisms

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