Explain SN1 mechanism of hydrolysis of tert–butyl chloride.
Answers
Explanation:
An example of a reaction taking place with an S
N
1
reaction mechanism is the hydrolysis of tert-butyl bromide with water forming tert-butanol-
tert-butyl bromide
(CH
3
)
3
C−Br
+2H
2
O⟶
tert-butanol
(CH
3
)
3
C−OH
+Br
−
+H
3
O
+
The above S
N
1
reaction takes place in three steps-
Formation of a tert-butyl carbocation by separation of a leaving group (Br
−
) from the carbon atom (this step is slow and reversible)-
(CH
3
)
3
C−Br⟶(CH
3
)
3
C
+
+Br
−
The carbocation reacts with the nucleophile. The intermediate is an oxonium ion (this reaction step is fast).
(CH
3
)
3
C
+
+H−O−H⟶(CH
3
)
3
C−H−
O
⊕
−H
Deprotonation will take place and alcohol will form along with hydronium ion (this reaction step is fast).
(CH
3
)
3
C−H−
O
⊕
−H+H−O−H⟶(CH
3
)
3
C−OH+H
3
O
+
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