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Chapter 5: Q.2 (page 177)

Classify each pair of compounds as constitutional isomers or stereoisomers.

Short Answer

Expert verified

The compounds in options a, b and c are all constitutional isomers and the compounds given in option d are stereoisomers.

Step by step solution

01

Constitutional Isomers

Compounds that have the same molecular formula but exist as different structures (i.e., adopts different structures) are termed as constitutional isomers.

02

Stereoisomers

The structures/compounds that differ only in the three-dimensional (3D) arrangement of atoms are referred to as stereoisomers.

03

Constitutional and Stereoisomers

a. Compounds 1 and 2 (from the left) differ only in the arrangement of groups i.e., they have the same molecular formula and different structural formula.

Therefore, the compounds in a are constitutional isomers.

b. In this case, the compounds differ only by their structure and hence they are constitutional isomers.

c. The two compounds differ in the position of the methyl groups i.e., there is a change in their structural formula.

Therefore, the given compounds are constitutional isomers.

d. The given compounds have the same molecular and structural formula, and they differ only by their arrangement in space i.e., the methyl groups in the given structures adopt different orientations.

Therefore, they are stereoisomers.

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Most popular questions from this chapter

A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.

Locate the stereogenic centers in each compound. A molecule may have zero, one, or more stereogenic centers. Gabapentin [part (d)] is used clinically to treat seizures and certain types of chronic pain. Gabapentin enacarbil [part (e)] is a related compound that is three times more potent.

a.

b.

c.

d.

e.

f.

Pure MSG, a common flavor enhancer, exhibits a specific rotation of +24. (a) Calculate the ee of a solution whose [α]is +10. (b) If the ee of a solution of MSG is 80%, what is [α]for this solution?

MSG

monosodium glutamate

Consider Newman projections (A–D) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.

Locate the stereogenic centers in each Newman projection and label each center as R or S.

a.

b.
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