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Chapter 22: Problem 2

For the following formulas, what types of isomerism could be exhibited? For each formula, give an example that illustrates the specific type of isomerism. The types of isomerism are structural, geometric, and optical. a. \(C_{6} \mathrm{H}_{12}\) b. \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) c. \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Br}_{2}\)

Short Answer

Expert verified
a. C6H12 can exhibit structural and geometric isomerism. Examples: Structural - Hex-1-ene and Hex-2-ene; Geometric - cis-Hex-2-ene and trans-Hex-2-ene. b. C5H12O can exhibit structural and optical isomerism. Examples: Structural - Pentan-1-ol and Pentan-2-ol; Optical - (R)-Pentan-2-ol and (S)-Pentan-2-ol. c. C6H4Br2 can only exhibit structural isomerism. Examples: Structural - Ortho-dibromobenzene, Meta-dibromobenzene, and Para-dibromobenzene. No examples for geometric or optical isomerism.

Step by step solution

01

Probable Isomerism for C6H12 (a)

In case of C6H12, it possible that structural isomerism, and geometric isomerism can be exhibited.
02

Example for each Isomerism of C6H12 (a)

1. Structural Isomerism: Hex-1-ene and Hex-2-ene are examples of structural isomers, as they have the same molecular formula \(C_{6}H_{12}\) but different arrangements of the double bond. 2. Geometric Isomerism: cis-Hex-2-ene and trans-Hex-2-ene are examples of geometric isomers, as they have the same molecular formula (C6H12) and the same arrangement of the double bond but different arrangements of substituents.
03

Probable Isomerism for C5H12O (b)

In case of C5H12O, it's possible that structural isomerism and optical isomerism can be exhibited.
04

Example for each Isomerism of C5H12O (b)

1. Structural Isomerism: Pentan-1-ol and Pentan-2-ol are examples of structural isomers, as they have the same molecular formula \(C_{5}H_{12}O\) but different positions of the hydroxyl group (OH). 2. Optical Isomerism: (R)-Pentan-2-ol and (S)-Pentan-2-ol are examples of optical isomers, as they have the same molecular formula (C5H12O), the same position of the hydroxyl group, and a chiral carbon center but are non-superimposable mirror images.
05

Probable Isomerism for C6H4Br2 (c)

In case of C6H4Br2, only structural isomerism and no other types of isomerism can be exhibited.
06

Example for each Isomerism of C6H4Br2 (c)

1. Structural Isomerism: Ortho-dibromobenzene, Meta-dibromobenzene, and Para-dibromobenzene are examples of structural isomers, as they have the same molecular formula \(C_{6}H_{4}Br_{2}\) but different positions of the bromine atoms on the benzene ring. 2. There are no chiral carbons or double bonds in dibromobenzenes, so there are no examples of geometric or optical isomerism exhibited by this molecular formula.

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