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Organic Chemistry | 8th Edition | ISBN: 9780321811394 | Authors: L.g. Wade, Jr.
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Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism Draw

Chapter 0, Problem 3-16

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QUESTION:

Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers. (a) 3-ethyl-1,1-dimethylcyclohexane (b) 1-ethyl-3-methylcycloheptane (c) 1-ethyl-3-methylcyclopentane (d) 1-cyclopropyl-2-methylcyclohexan

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QUESTION:

Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers. (a) 3-ethyl-1,1-dimethylcyclohexane (b) 1-ethyl-3-methylcycloheptane (c) 1-ethyl-3-methylcyclopentane (d) 1-cyclopropyl-2-methylcyclohexan

ANSWER:

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Certain disubstituted cycloalkanes show cis and trans isomerism (geometric isomerism). When two different substituents are present on two different carbon atoms in a disubstituted cycloalkane, cis and trans isomerism is possible. However, if two same substituents are present on two different carbon atoms in a disubstituted cycloalkane, cis and trans isomerism is NOT possible. Also, if two same substituents are present on the same carbon atom in a disubstituted cycloalkane, cis and trans isomerism is NOT possible.

In the cis isomer of disubstituted cycloalkane, two substituents are present on the same side of the plane of the ring. In the trans isomer of disubstituted cycloalkane, two substituents are present on the opposite side of the plane of the ring.

 

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