Formation of tosylates from alcohols
Description: Treatment of alcohols with p-toluenesulfonyl chloride (TsCl) results in the formation of tosylates, which is an excellent leaving group.
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Why does Cl- in step 3 act as a base, not a nucleophile that attacks C in the C-O bond, because after the pronation step, the O(+)Ts becomes a good leaving group?
Good question! With primary alkyl tosylates, that reaction is plausible, but slow.
However, it turns out that with *allylic* toslyates (e.g. H2C=CHCH2OTs) the reaction is a lot faster and will often result in allylic chlorides. You likely won’t see any examples in your course, but it is something to watch out for in the lab.
Is this reaction possible if Methyl group were not there on the benzene ring?
Yes, except it wouldn’t be tosylate, it benzenesulfonyl.
I thought it was TosCl instead of TsCl???
Either can be used.
Excellent. I was reading Kaplan MCAT review and messed up with this reaction. This page gives clarity of thought that may be needed to do good on MCAT….
it’s excellent……..