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deleted 20 characters in body; edited title

edited Dec 2, 2016 at 20:14

How to determine the most reactive hydroxy group of α-ᴅ-glucopyranose?

So here's the problem:

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I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

asked Jun 17, 2015 at 19:37

justbehappy

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