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Chapter 5: Q.15 (page 190)

a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.

b. Label each stereogenic centre as R or S.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Stereogenic center

The stereogenic center is the center where four different groups are attached.

02

R and S nomenclature

The R and S nomenclature is obtained by giving the ranking according to the priority.

The clockwise rotation is known as R configuration, and anticlockwise rotation is assigned as S configuration.

03

Skeletal structure of Lisinopril

The skeletal structure of Lisinopril is shown as:

04

Explanation

a. In the given compound, there are three stereogenic centers.

Stereogenic centers

b. The order of priority of the groups at chiral centers are shown as:

NH>COOH>R>H

Therefore, all the movements in lisinopril are anticlockwise. Therefore, all the stereogenic centers are S.

Configurations of Stereogenic centres

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Most popular questions from this chapter

Locate the tetrahedral stereogenic center(s) in each compound. A molecule may have one or more stereogenic centers.

a.

b.

c.

d.

e.

f.

What is the ee for each of the following mixtures of enantiomers A and B?

a. 95% A and 5% B

b. 85% A and 15% B

Label each compound as R or S.

a.

b.

c.

d.

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

A molecule is achiral if it has a plane of symmetry in any conformation. Each of the following conformations does not have a plane of symmetry, but rotation around a carbon–carbon bond forms a conformation that does have a plane of symmetry. Draw this conformation for each molecule.

a.

b.
See all solutions

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