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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

Rank the following groups in order of decreasing priority?

a.-COOH,-H,-NH2,-OH

b.-CH2CH3,-CH3,-H,-CH(CH3)2

c.-H,-CH3,-Cl,-CH2Cl

d.-CH=CH2,CH3,颁鈮贬,-贬

Give the IUPAC name for each compound, including the R,S designation for each stereogenic center.

a.

b.

c.

Label the stereogenic centers in paclitaxel, the chapter-opening anticancer drug, as R or S.

Label each compound as chiral or achiral.

a.

b.

c.

d.

Draw the structures for each compound.

  1. (R)-3-methylhexane
  2. (4R,5S)-4,5-diethyloctane
  3. (3R,5S,6R)-5-ethyl-3,6-dimethylnonane
  4. (3S,6S)-6-isopropyl-3-methyldecane
See all solutions

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