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Chapter 5: Q.13 (page 190)

Label each compound as R or S.

a.

b.

c.

d.

Short Answer

Expert verified

a. S isomer.

b. S isomer.

c. R isomer.

d. S isomer.

Step by step solution

01

R and S nomenclature

The R and S nomenclature is assigned to the given molecule as follows:

  • The molecules having high molecular masses are given as the first priority.


The order of the priority of some groups is: H<C<N<O<S<Cl<Br<I

  • The double bonded groups also have the highest priority because it is multiplied by the same group in the place of a bond. For example, C=O is equivalent to CC-OO.
  • The clockwise movement based on the priority gives R configuration, and the anticlockwise movement gives S configuration.

If the lowest priority group is above the plane, then the R is inverted into S and vice versa.

02

Explanation

a. The order of priority is shown as:

Br>Cl>CH3>H

Therefore, the movement is anticlockwise.

Representation of S isomer

b. The order of priority is shown as:

OH>COOH>CH3>H

Therefore, the movement is anticlockwise.

Representation of S isomer

c. The order of priority is shown as:

CH2CH2CH(CH3)CH>CH2CH2CH2CH2>CH3>H

Therefore, the movement is clockwise.

Representation of R isomer

d. The order of priority is shown as:

OH>CH2Cl>CH2CH2Br>CH3

Therefore, the movement is clockwise.

Representation of S isomer

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Most popular questions from this chapter

Draw a meso compound for each of the following molecules.

a.

b.

c.

Consider Newman projections (A鈥揇) 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.

How is each compound related to the simple sugar D-erythrose? Is it an enantiomer,diastereomer, or identical?

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b.

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The shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.

a. Draw the structure of naturally occurring (鈥�)-ephedrine, which has the 1R,2Sconfiguration.

b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.

c. How are ephedrine and pseudoephedrine related?

d. Draw all other stereoisomers of (鈥�)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

e. How is each compound drawn in part (d) related to (鈥�)-ephedrine?

The facts in Section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in 2007 for the treatment of hypertension.
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