Consider the relative rates of the two solvolysis reactions in acetic acid solvent shown in Fig. P17.50.

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(a) Suggest a reason that compound A undergoes solvolysis much faster than compound B.

(b) Account for the retention of stereochemistry observed in reaction A with a mechanism. 52=5 +Na+ ACO HOAC H CI A H CI E-~= +Na+ ACO B Figure P17.50 HOAC H OAC H OAc + Na* Cr relative rate 101 =

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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Question Posted: Dec 10, 2023 10:26 AM

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Consider the relative rates of the two solvolysis reactions in acetic acid solvent shown in Fig. P17.50.

Question:

5₁2=5₁ +Na+ ACO™ HOAC H CI H A CI E-~= +Na+ ACO™ B Figure P17.50 HOAC H OAC H OAc +Na+ Cr + Na¹ CI relative rate 10¹1 = relative rate=1 ACO H none formed

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a Solvolysis reactions are faster when the carbocation intermediate is stabilized The only diff...View the full answer

Organic Chemistry

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