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Magazine Chapter 5: Q.62 (page 209)
How is compound A related to compounds B鈥揈? Choose from enantiomers, diastereomers, constitutional isomers, or identical molecules.
Short Answer
Compound A and Compound B are diastereomers.
Compound A and Compound C are identical molecules.
Compound A and Compound D are enantiomers.
Compound A and Compound E are constitutional isomers.
Step by step solution
Enantiomers and Diastereomers
The R, S configuration is different for enantiomers, but one stereocenter will have a similar configuration in the diastereomer.An example of an enantiomer is lactic acid, and that of a diastereomer is tartaric acid.
Constitutional isomers
An isomer pair that possesses a matching molecular formula but has different connectivity are constitutional isomers.An example of a constitutional isomer is butane and isobutane.
Relation of compound A with compounds B, C, D, and E
Relation of compound A with compound B
Compounds A (trans, R) and B (cis, R) have different geometry around the double bond and the same configuration around the stereogenic center. Hence, compounds A and B are diastereomers.
Relation of compound A with compound C
Compounds A(trans, R) and C(trans, R) have the same geometry around the double bond and the same configuration around the stereogenic center. Hence,compounds A and C are identical.
Relation of compound A with compound D
Compounds A (trans, R) and D (trans, S) have the same geometry around the double bond and different configurations around the stereogenic center. Hence,compounds A and D are enantiomers.
Relation of compound A with compound E
Compounds A (trans, R) and E have the same molecular formula but varying connectivity. Hence,compounds A and E are constitutional isomers.
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