Question

Consider the following reactions:

$I.M{e}_{3}C-Cl\stackrel{\stackrel{\ominus }{OH}}{\to }M{e}_{3}C-OHII.F_{3}C-\underset{\underset{Me}{|}}{CH}-Cl\stackrel{\stackrel{\ominus }{OH}}{\to }{F}_{3}C-\underset{\underset{Me}{|}}{CH}-OHIII.M{e}_{3}C-Cl\stackrel{90\%D_{2}O+10\%ether}{\to }M{e}_{3}C-ODIV.M{e}_{3}C-Cl\stackrel{90\%H_{2}O+10\%ether}{\to }M{e}_{3}C-OH$

Which of the following statements are correct?

• A. Reaction (I) is faster than (II).
• B. Reaction (II) is faster than (I).
• C. Reaction (III) is faster than (IV).
• D. Reaction (IV) is faster than (III).

Answer 1

Answer: (B), (D)

Reaction (IV) is faster than (III).

i. In (II), carbocation is destabilised by stronger -I effect of three F atoms, and thus solvolysis of (II) is slower than that of (I).

ii. D -bonds are not as stabilising as H-bonds. So reaction (IV) is faster than (III).