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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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Draw both enantiomers for each biologically active compound.

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Draw in a plane of symmetry for each molecule.

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A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.

贬颁鈮-颁鈮-颁贬=颁=颁贬-颁贬=颁贬-颁贬=颁贬-颁贬2CO2H

Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.

  1. Locate the stereogenic centers in both drugs.
  2. Label each stereogenic center in mefloquine as R or S.
  3. What is the maximum number of stereoisomers possible for artemisinin?
  4. How are the N atoms in mefloquine hybridized?
  5. Can two molecules of artemisinin intermolecularly hydrogen bond to each other?
  6. What product is formed when mefloquine is treated with HCl?

Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A鈥揇) in Figure 5.8 are identical to E and F?
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