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Chapter 5: Question 5.33 (page 281)

(+)-Tartaric acid has a specific rotation of +12.0掳. Calculate the specific rotation of a mixture of 68% (+)@tartaric acid and 32% (-)@tartaric acid.

Short Answer

Expert verified

Answer:

Specific rotation = 4.3

Step by step solution

01

Introduction

The optical purity of a mixture is defined as the ratio of its rotation to the rotation of a pure enantiomer. The enantiomeric excess (e.e.) is a more common method for expressing the relative amounts of enantiomers in a mixture. To compute the enantiomeric excess of a mixture, we calculate the excess of the predominant enantiomer as a percentage of the entire mixture.

02

Optical Rotation

o.p. = e.e. = |d-l|x 100%

|d+l|

(Where, o.p = optical purity, e.e=enantiomeric excess,d=68% and l=32%)

03

Enantiomeric excess

e.e = 68-32 x 100 = 36%

68+32

04

Optical rotation of mixture

Therefore,

Optical rotation of this mixture = 36% x (+12.0掳)

= 4.3

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Most popular questions from this chapter

  1. Make a model of each compound, draw it in its most symmetric conformation, and determine whether it is capable of showing optical activity.
  1. 1-bromo-1-chloroethane
  2. 1-bromo-2-chloroethane
  3. 1,2-dichloropropane
  4. Cis-1,3-dibromocyclohexane
  5. Trans-1,3-dibromocyclohexane
  6. Trans-1,4-dibromocyclohexane.

2.Star (*) each asymmetric carbon atom in part (1), label each as (R) or (S) and compare your result from part (1) with the prediction you would make based on the asymmetric carbons.

Question: For each pair, give the relationship between the two compounds. Making models will be helpful.

(a) (2R,3S)-2,3-dibromohexane and (2S,3R)-2,3-dibromohexane

(b) (2R,3S)-2,3-dibromohexane (2R,3R)-2,3-dibromohexane

(c)

(d)

(e)

(f)

(g)

(h)

(i)

The following structures are optically active compounds. Star (*) the asymmetric carbon atoms in these structures.

Question: For each of the compounds described by the following names,

1. draw a three-dimensional representation

2. star (*) each chiral center

3. draw any planes of symmetry.

4. draw any enantiomer.

5. draw any diastereomers.

6. label each structure you have drawn as chiral or achiral

(a) (S)-2-chlorobutane

(b)(R)-1,1,2-trimethylcyclohexane

(c) (2R,3S)-2,3-dibromohexane

(d) (1R,2R)-1,2-dibromocyclohexane

(e) meso-hexane-3,4-diol,CH3CH2CH(OH)CH(OH)CH2 CH3

(f) 卤-hexane-3,4-diol

Convert the following Fischer projections to perspective formulas.
See all solutions

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