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Chapter 5: Q.49 (page 207)

Draw the structures of (S,S)-ethambutol, a drug used to treat tuberculosis that is 10 times more potant than any of its other isomers.

ethambutol

Short Answer

Expert verified

Following is the structure of (S,S)-ethambutol:

Step by step solution

01

Definition of stereoisomers

The stereoisomers are also known as spatial isomers. These are the kind of isomers with similar molecular formulas and also the same sequence of bonds.

The stereoisomers differ from each other only in the three-dimensional positionings of their atoms. They are further classified as enantiomers and diastereomers.

02

The structure of (S,S)-ethambutol

It is a drug used for the treatment of tuberculosis.

Structure of (S,S)-ethambutol

It consists of two stereogenic carbon atoms as marked in the structure by *.

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Most popular questions from this chapter

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?

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?

Which compounds are meso compounds?

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b.

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Cellulose is water insoluble, despite its many OH groups. Considering its three-dimensional structure, why do you think this is so?
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