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Using a planar pentagon representation for the cyclopentane ring, draw structural formulas for the cis and trans isomers of the following. (a) 1,2 -Dimethylcyclopentane (b) 1,3 -Dimethylcyclopentane

Short Answer

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Question: Draw the structural formulas for cis and trans isomers of 1,2-dimethylcyclopentane and 1,3-dimethylcyclopentane. Answer: For cis-1,2-dimethylcyclopentane, the two methyl groups are on the same side of the cyclopentane ring and attached to carbon-1 and carbon-2. In the trans-isomer, the methyl groups are on opposite sides, still attached to carbon-1 and carbon-2. For cis-1,3-dimethylcyclopentane, the methyl groups are on the same side of the cyclopentane ring, attached to carbon-1 and carbon-3. In the trans-isomer, the methyl groups are on opposite sides, attached to carbon-1 and carbon-3.

Step by step solution

01

Draw the basic cyclopentane ring structure

Draw a regular pentagon, which is a 5-sided polygon with equal side lengths, to represent the cyclopentane ring.
02

Identify the position of methyl groups in 1,2-dimethylcyclopentane

Methyl groups are attached to carbon-1 and carbon-2 in the 1,2-dimethylcyclopentane. Label one of the vertices of the pentagon as carbon-1, the adjacent vertex as carbon-2, and continue labeling the remaining vertices up to carbon-5.
03

Draw the cis-isomer for 1,2-dimethylcyclopentane

For cis-1,2-dimethylcyclopentane, the two methyl groups should be on the same side of the cyclopentane ring. Attach a methyl group (CH3) to carbon-1 and carbon-2, directing both towards the same side (either right or left of the ring).
04

Draw the trans-isomer for 1,2-dimethylcyclopentane

For trans-1,2-dimethylcyclopentane, the two methyl groups should be on opposite sides of the cyclopentane ring. Attach a methyl group (CH3) to carbon-1 and carbon-2, directing them towards opposite sides (one right and one left of the ring).
05

Identify the position of methyl groups in 1,3-dimethylcyclopentane

Methyl groups are attached to carbon-1 and carbon-3 in 1,3-dimethylcyclopentane. Label one of the vertices of the pentagon as carbon-1, the next adjacent vertex as carbon-2, the next adjacent as carbon-3, and continue labeling the remaining vertices up to carbon-5.
06

Draw the cis-isomer for 1,3-dimethylcyclopentane

For cis-1,3-dimethylcyclopentane, the two methyl groups should be on the same side of the cyclopentane ring. Attach a methyl group (CH3) to carbon-1 and carbon-3, directing both towards the same side (either right or left of the ring).
07

Draw the trans-isomer for 1,3-dimethylcyclopentane

For trans-1,3-dimethylcyclopentane, the two methyl groups should be on opposite sides of the cyclopentane ring. Attach a methyl group (CH3) to carbon-1 and carbon-3, directing them towards opposite sides (one right and one left of the ring).

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Most popular questions from this chapter

Name and draw structural formulas for all cycloalkanes with molecular formula \(\mathrm{C}_{5} \mathrm{H}_{10}\). Include cis and trans isomers as well as constitutional isomers.

\(1,2,3,4,5,6\)-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans3,6-hexachlorocyclohexane. (a) Draw a structural formula for \(1,2,3,4,5,6\)-hexachlorocyclohexane disregarding, for the moment, the existence of cis, trans isomerism. What is the molecular formula of this compound? (b) Using a planar hexagon representation for the cyclohexane ring, draw a structural formula for lindane. (c) Draw a chair conformation for lindane and label which chlorine atoms are axial and which are equatorial. (d) Draw the alternative chair conformation of lindane and again label which chlorine atoms are axial and which are equatorial. (e) Which of the alternative chair conformations of lindane is more stable? Explain.

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