The rates of acetolysis for the following norbornyl derivatives are in the order P Q R · ABC26OR0848
Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Exam: JAM 2005-2022 · Marks: 2 · Difficulty: Easy
The rates of acetolysis for the following norbornyl derivatives are in the order 
P 
Q 
R
P Q R(a)$\mathrm{R} > \mathrm{Q} > \mathrm{P}$
(b)$\mathrm{Q} > \mathrm{R} > \mathrm{P}$
(c)$\mathrm{P} > \mathrm{R} > \mathrm{Q}$
(d)$\mathrm{R} > \mathrm{P} > \mathrm{Q}$
Answer
Answer: D ✓ checked by 4AB · confidence medium
Explanation
Acetolysis of the norbornenyl tosylate with OTs anti to the C=C is about 10¹¹ times faster than the saturated 7-norbornyl case, because of π participation. The syn isomer is only moderately assisted. The chapter key gives R > P > Q (d).
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