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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. \(\mathrm{C}_{6} \mathrm{H}_{12}\) 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. Example: Structural - Hexene and Methylpentene. Geometric - (Z)-hex-2-ene and (E)-hex-2-ene. b. C5H12O can exhibit structural and optical isomerism. Example: Structural - Pentanol and 2-methylbutanol. Optical - R-2-butanol and S-2-butanol. c. C6H4Br2 can exhibit structural isomerism. Example: Structural - ortho-dibromobenzene, meta-dibromobenzene, and para-dibromobenzene.

Step by step solution

01

Isomerism definition

Isomerism occurs when two or more molecules have the same chemical formula but different molecular structures. There are three types of isomerism: structural, geometric, and optical isomerism. Step 2: Identifying possible isomerism in each molecular formula
02

a. C6H12

C6H12 is an alkene with six carbon atoms, and it can exhibit both structural isomerism and geometric isomerism. No optical isomerism can occur in this compound since there are no carbon atoms with four different groups attached to them (chiral centers). Example: Structural - Hexene and Methylpentene (both have different arrangements of carbon atoms). Geometric - (Z)-hex-2-ene (cis-isomer) and (E)-hex-2-ene (trans-isomer) differ only in the position of the substituents.
03

b. C5H12O

C5H12O is an alcohol with five carbon atoms and one hydroxyl group. It can exhibit structural isomerism and optical isomerism, but not geometric isomerism since it does not contain carbon-carbon double bonds. Example: Structural - Pentanol and 2-methylbutanol (different arrangements of carbon and hydroxyl group). Optical - 2-butanol has a chiral center, so it has two enantiomers: R-2-butanol and S-2-butanol (they are mirror images of each other).
04

c. C6H4Br2

C6H4Br2 is a brominated benzene derivative with two bromine atoms. It can exhibit structural isomerism, but not geometric or optical isomerism since it does not contain carbon-carbon double bonds or chiral centers. Example: Structural - ortho-dibromobenzene, meta-dibromobenzene, and para-dibromobenzene (differ in the relative positions of the bromine atoms on the benzene ring).

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Most popular questions from this chapter

All amino acids have at least two functional groups with acidic or basic properties. In alanine, the carboxylic acid group has \(K_{\mathrm{a}}=4.5 \times 10^{-3}\) and the amino group has \(K_{\mathrm{b}}=7.4 \times 10^{-5}\) Three ions of alanine are possible when alanine is dissolved in water. Which of these ions would predominate in a solution with \(\left[\mathrm{H}^{+}\right]=1.0 M ?\) In a solution with \(\left[\mathrm{OH}^{-}\right]=1.0 M ?\)

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