Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 7, Problem 70P
Interpretation Introduction

(a)

Interpretation: The products formed by the reaction of alkyl bromide A with a single enantiomer of amino ester B are to be predicted.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The racemic mixture contains same amount of compounds that has S and R configuration.

Interpretation Introduction

(b)

Interpretation: The product that is needed to synthesize the quinapril is to be identified.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The racemic mixture contains same amount of compounds that has S and R configuration.

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Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an OH group. 2-methylcyclohexanone
(a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?

Chapter 7 Solutions

Organic Chemistry (6th Edition)

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