Q36 P Naproxen, a nonsteroidal anti-in... [FREE SOLUTION]

Chapter 4: Q36 P (page 143)

Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation result in a mixture with a 97% enantiomeric excess.
a. Does naproxen have the R or the S configuration?
b. What percent of each enantiomer is obtained from the commercial preparation?

Short Answer

Expert verified

Cannot be determined
Commercial preparation forms 98.5% (+) naproxen and 1.5% (-) naproxen.

Step by step solution

Definition of specific rotation-

The observed rotation can be used to calculate the specific rotation at a given temperature and wavelength using the formula-

[饾灙] = $\frac{伪}{l 脳 c}$

where, [饾灙] is the specific rotation,

T is the temperature in degrees Celsius,

l is the wavelength of the incident light (when the sodium D-line is used, l is indicated as D),

蓱 is the observed rotation,

l is the length of the sample tube in decimetres, and

c is the sample concentration in grams per 100 millilitres.

Given quantities-

specific rotation of Naproxen = +66

enantiomeric excess on commercial preparation = 97%

Step 3:

97% of commercial preparation is (+)-naproxen: 3% of racemic mixture.

Calculation of specific rotation of naproxen-

Enantiomeric excess = $\frac{a b s e r v e d s p e c i f i c r o t a t i o n}{s p e c i f i c r o t a t i o n o f p u r e (+) e n a n t i o m e r}$ 脳 100%

97% = $\frac{x}{66}$ 脳 100

X = +64.02

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Short Answer

Step by step solution

Definition of specific rotation-

Given quantities-

Step 3:

Calculation of specific rotation of naproxen-

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