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Chemistry / Organic Chemistry 2 / Chapter 22 / Problem 22.105

Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein

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Consider the structures of the constitutional isomers,

Chapter 22, Problem 22.105

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QUESTION:

Consider the structures of the constitutional isomers, compound A and compound B. When treated with aqueous acid, compound A undergoes isomerization to give a cis stereoisomer. In contrast, compound B does not undergo isomerization when treated with the same conditions. That is, compound B remains in the trans configuration. Explain the difference in reactivity between compound A and compound B. O Compound A Compound B O

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QUESTION:

Consider the structures of the constitutional isomers, compound A and compound B. When treated with aqueous acid, compound A undergoes isomerization to give a cis stereoisomer. In contrast, compound B does not undergo isomerization when treated with the same conditions. That is, compound B remains in the trans configuration. Explain the difference in reactivity between compound A and compound B. O Compound A Compound B O

ANSWER:

Step 1 of 3

Consider the structures of the two following constitutional isomers.

The reaction of compound A with aqueous acid leads to isomerization, giving a cis stereoisomer. However, when compound B is treated with aqueous acid it stays in the same configuration. Explain this difference in reactivity between compound A and compound B.

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