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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

Consider Newman projections (A–D) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.

A natural product was isolated in the laboratory, and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of water. What is the specific rotation of this compound?

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

a. 95% A and 5% B

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A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.

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