(b) Complete the following reaction and
write the mechanism :
.
C(CH3)3
F3CCOOOH
→ ?
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Answer:
The alkaline hydrolysis of tertiary butyl bromide gives tert butanol.
(CH
3
)
3
CBr+OH
(aq)
−
→(CH
3
)
3
COH+Br
(aq)
−
The reaction proceeds through SN
1
mechanism. Tert butyl bromide dissociates to give stable tertiary carbocation. This is rate determining step.
(CH
3
)
3
CBr→(CH
3
)
3
C
+
+Br
(aq)
−
The carbocation then combines with hydroxide ion to form tert butanol. This is fast step.
(CH
3
)
3
C
+
+OH
(aq)
−
→(CH
3
)
3
COH
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