Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 23P
Interpretation Introduction

Interpretation:

The product obtained from the reaction of D-ribose with one equivalent of methanol and HCl is to be predicted.

Concept Introduction:

The hydroxyl group of anomeric carbon is protonated by an acid.  The lone pair on the ring helps in eliminating a molecule of water which results in the formation of oxocarbenium ion.  It is planar molecule.  When the alcohol approaches from the top of the plane, the β-glycoside is formed.  When the alcohol approaches from the bottom of plane, the α-glycoside is formed.

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