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Chapter 22: Problem 42

R For which of the following is geometric isomerism possible? (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CCl}_{2}\) (b) \(\mathrm{CH}_{3} \mathrm{ClC}=\mathrm{CCH}_{3} \mathrm{Cl}\) (c) \(\mathrm{CH}_{3} \mathrm{BrC}=\mathrm{CCH}_{3} \mathrm{Cl}\)

Short Answer

Expert verified
a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CCl}_{2}\) b) \(\mathrm{CH}_{3} \mathrm{ClC}=\mathrm{CCH}_{3} \mathrm{Cl}\) c) \(\mathrm{CH}_{3} \mathrm{BrC}=\mathrm{CCH}_{3} \mathrm{Cl}\) Answer: Molecules (b) and (c) exhibit geometric isomerism.

Step by step solution

01

Case (a)

For molecule (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CCl}_{2}\): Each carbon atom of the double bond needs to have two different substituents attached. In this case, the left-side carbon has two methyl groups attached to it, and the right-side carbon has two chlorine atoms attached to it. Since both carbon atoms are connected to the same groups, molecule (a) does not exhibit geometric isomerism.
02

Case (b)

For molecule (b) \(\mathrm{CH}_{3} \mathrm{ClC}=\mathrm{CCH}_{3} \mathrm{Cl}\): The left-side carbon atom in the double bond is attached to a methyl group and a chlorine atom, while the right-side carbon atom is attached to a methyl group and a chlorine atom as well. Both carbon atoms of the double bond are connected to two different groups, so molecule (b) exhibits geometric isomerism.
03

Case (c)

For molecule (c) \(\mathrm{CH}_{3} \mathrm{BrC}=\mathrm{CCH}_{3} \mathrm{Cl}\): The left-side carbon atom in the double bond is attached to a methyl group and a bromine atom, while the right-side carbon atom is attached to a methyl group and a chlorine atom. Both carbon atoms of the double bond are connected to two different groups, so molecule (c) exhibits geometric isomerism. In conclusion, geometric isomerism is possible for molecules (b) and (c).

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Most popular questions from this chapter

Draw the structural isomers of \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{Cl}_{2}\) in which two of the hydrogen atoms of \(\mathrm{C}_{3} \mathrm{H}_{8}\) have been replaced by chlorine atoms.

Draw the structural isomers of the alkene \(\mathrm{C}_{4} \mathrm{H}_{8}\)

Name the products formed when the following reagents add to 1-butene. (a) \(\mathrm{H}_{2}\) (b) \(\mathrm{Br}_{2}\)

When the conjugate acid of aniline, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{ }^{+}\), reacts with the acetate ion, the following reaction takes place: \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{ }^{+}(a q)+\mathrm{CH}_{3} \mathrm{COO}^{-}(a q) \rightleftharpoons \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}(a q)+\mathrm{CH}_{3} \mathrm{COOH}(a q)\) If \(K_{\mathrm{a}}\) for \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{ }^{+}\) is \(1.35 \times 10^{-5}\) and \(K_{\mathrm{a}}\) for \(\mathrm{CH}_{3} \mathrm{COOH}\) is \(1.86 \times 10^{-5}\) what is \(K\) for the reaction?

In each of the following, name the functional group (i.e., ester, aldehyde, ...). (a) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}-\mathrm{OH}\)
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