Are the following pairs identical, enantiomers, diastereomers, or constitutional

Question

Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers? a. A solution is prepared by dissolving 400 mg of testosterone, a male sex hormone, in 10.0 mL of ethanol and placing it in a sample tube 10.0 cm in length. The observed rotation of this sample at 25 degree C using the D line of sodium is +4.360 degree. Calculate the specific rotation of testosterone. b. One commercial synthesis of naproxen (the active ingredient in Aleve and a score of other over-the-counter and prescription nonsteroidal anti-inflammatory drug preparations) gives the enantiomer shown in 97% enantiomeric excess. i. Assign an R or S configuration to this enantiomer of naproxen. ii. What are the percentages of R and S enantiomers in the mixture?

Explanation / Answer

4. (a) the pair are Diastereomers

Stereoisomers are divided into two parts (i).Diastereomers: they are pairs of isomers that have opposite configurations at one or more of the chiral centers and not mirror images of each other, (ii). Enantiomers are the mirror images of each other.

(b) and (c) these pairs are Constitutional isomers

Constitutional isomers have same molecular formula but different molecular structures due to different type of arrangement of atoms in their molecules. They differ in the order in which the atoms are connected with each other thus they contain different functional groups and or bonding patterns like branching.

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