/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q85E When glucose (Problem 19-52) is ... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 19: Q85E (page 648)

When glucose (Problem 19-52) is treated with NaBH4 , reaction occurs to yield sorbitol, a polyalcohol commonly used as a food additive. Show how this reduction occurs.

Short Answer

Expert verified

Reduction followed as:

Step by step solution

01

Reduction with sodium borohydride

Sodium borohydride NaBH4 is the mild reducing agent which is used to reduce the aldehyde and ketone carbonyl group to the alcohol. It reduces aldehyde to primary alcohol and ketone to secondary alcohol it do not reduce the higher carbonyl like carboxylic acid and ether so, it is a mild reagent.

02

Reduction of glucose with sodium borohydride

As glucose contain the aldehyde group and sodium borohydride is the basic reducing agent so it abstracts the proton of the aldehyde followed by hydrolysis convert the carbonyl into the hydroxyl group as the primary alcohol is formed in sorbitol as shown below:

Reduction of Glucose

03

Reduction of glucose

Reduction of glucose to form sorbitol is followed by hydrolysis by converting the open aldehyde to alcohol group.

Compound Formation

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

The Wharton reaction converts an epoxy ketone to an allylic alcohol by reaction with hydrazine. Propose a mechanism. (Hint: Review the Wolff鈥揔ishner reaction in Section 19-9.)

Predict the product(s) and provide the mechanism for each reactionbelow. What does each mechanism have in common?

How might you use mass spectrometry to distinguish between the following pairs of isomers?

(a) 3-Methyl-2-hexanone and 4-methyl-2-hexanone

(b) 3-Heptanone and 4-heptanone

(c) 2-Methylpentanal and 3-methylpentanal

Choose the structure that best fits the IR spectrum shown.

Compound A, C8H10O2, has an intense IR absorption at 1750cm-1 and gives the 13C NMR spectrum shown. Propose a structure for A.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.