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The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the

Chapter 7, Problem 7-47

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QUESTION:

The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the trans isomer of 4,4-dimethylpent2-ene is nearly 16 kJ/mol more stable than the cis isomer. Explain this large difference.

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QUESTION:

The energy difference between cis- and trans-but-2-ene is about 4 kJ/mol; however, the trans isomer of 4,4-dimethylpent2-ene is nearly 16 kJ/mol more stable than the cis isomer. Explain this large difference.

ANSWER:

Step 1 of 3

In dimethylpent2-ene, bulky groups are present across the double bond.

In case of cis4,4-dimethylpent2-ene, the bulky groups are present along the same as shown in the figure.

                                             

Due to this, there is a lager steric hindrance. This causes repulsion between the methyl group and tertiary butyl group.

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