Introduction To General, Organic, And Biochemistry
Introduction To General, Organic, And Biochemistry
12th Edition
ISBN: 9781337571357
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 19, Problem 30P
Interpretation Introduction

Interpretation:

The name and structure of the alditol formed by reduction of NaBH4 D-fructose other than the D-sorbitol should be determined.

Concept Introduction:

The sodium borohydride is a reducing agent, so it reduces the functional group present in the carbohydrate and itself get oxidized.

The reduction of aldehyde results in the formation of alcohol because reduction can also be defined as addition of hydrogen atom thus, -CHO group becomes -CH2 OH after addition of two hydrogen atoms on carbonyl carbon of the aldehydic group.

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Are the products of the given reaction correct?  Why or why not?
The question below asks why the products shown are NOT the correct products.  I asked this already, and the person explained why those are the correct products, as opposed to what we would think should be the correct products.  That's the opposite of what the question was asking.  Why are they not the correct products? A reaction mechanism for how we arrive at the correct products is requested ("using key intermediates").  In other words, why is HCl added to the terminal alkene rather than the internal alkene?
My question is whether HI adds to both double bonds, and if it doesn't, why not?

Chapter 19 Solutions

Introduction To General, Organic, And Biochemistry

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