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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

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

Draw all possible constitutional and stereoisomers for a compound of molecular formulaC6H12 having a cyclobutane ring and two methyl groups as substituents. Label each compound as chiral or achiral.

Drawn are four isomeric dimethylcyclopropanes.

a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?

b. Label each compound as chiral or achiral.

c. Which compounds, alone, would be optically active?

d. Which compounds have a plane of symmetry?

e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?

f. Which of the compounds are meso compounds?

g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?

Determine if each compound is identical to or an enantiomer of A.

a.

b.

c.

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
See all solutions

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