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5-Chloro-1,3-cyclopentadiene (below) undergoes SN1 solvolysis in the presence of silver

Chapter 14, Problem 14.27

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QUESTION:

5-Chloro-1,3-cyclopentadiene (below) undergoes SN1 solvolysis in the presence of silver ion extremely slowly even though the chlorine is doubly allylic and allylic halides normally ionize readily (Section 15.15). Provide an explanation for this behavior.

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QUESTION:

5-Chloro-1,3-cyclopentadiene (below) undergoes SN1 solvolysis in the presence of silver ion extremely slowly even though the chlorine is doubly allylic and allylic halides normally ionize readily (Section 15.15). Provide an explanation for this behavior.

ANSWER:


The presence of the increased steric hindrance caused by the two double bonds on either side of the chl

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