From Mcmurry's organic chemistry 9th edition chapter 18, problem 3p --> (c) why do we use isop...
From Mcmurry's organic chemistry 9th edition chapter 18, problem 3p --> (c) why do we use isopropanol with benzyl bromide instead of isopropyl bromide and benzyl alcohol?
Homework Answers
reaction of benzyl bromide with isopropanol will give benzyl isopropyl ether whereas reaction of isopropyl bromide and benzyl alcohol will not lead to benzyl isopropyl ether
explanation:
reaction of benzyl bromide with isopropanol will undergo by SN1 mechanism
in first step benzyl carbocation is generated, the carbocation is stabilized by resonance
in second step isopropanol attack the benzyl carbocation to form benzyl isopropyl ether as product
whereas when we treat isopropyl bromide with benzyl alcohol reaction should undergo by SN2 mechanism, for SN2 mechanism we need strong nucleophilie but benzyl alcohol is poor nucleophilie therefore reaction of isopropyl bromide with benzyl alcohol is not suitable method
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