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Chapter 18: Q57P (page 971)

Both NaBH4 and NaBD4 are commercially available, and D2O is common and inexpensive. Show how you would synthesize the following labelled compounds, starting with propanone.

Short Answer

Expert verified

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

Step by step solution

01

Introduction

Sodium borohydride (NaBH4) or sodium borodeuteride (NaBD4) is used as a reducing agent which reduces aldehyde or ketone to its corresponding alcohol.

02

Reduction of ketone with NaBH4 or NaBD4  in presence of H2O or  D2O

Ketones on treatment with NaBD4 followed by hydrolysis with H20 yields a product in which the carbonyl group is reduced to hydroxyl group . Also, ketones on treatment with NaBD4 followed by hydrolysis with D20 yields a product in which the carbonyl group is reduced to hydroxyl group where D atom is present in place of H atom.

03

Synthesis of the given compounds from propanone (a ketone)

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Most popular questions from this chapter

Predict the products formed when cyclopentanecarbaldehyde reacts with the following reagents.

(a) PhMgBr, then H3O+

(b) Tollens reagent

(c) semicarbazide and weak acid

(d) excess ethanol and acid

(e) propane-1-3-diol, H+

(f) zinc amalgam and dilute hydrochloric acid

Draw the structures of the following derivatives.

(a) the 2,4-dinitrophenylhydrazone of acetone

(b) the semicarbazone of cyclopentanone

(c) cyclcobuanone oxime

(d) the ethylene acetal of hexan-2-one

(e) acetaldehyde diethyl acetal

(f) the ethyl hemiacetal of acetaldehyde

(g) the (Z) isomer of the ethyl imine of propiophenone

(h) the hemiacetal form of 6-hydroxyhexanal

PROBLEM 18-10

Predict the products of the following reactions:

Propose mechanisms for

(a) the acid-catalyzed hydration of chloral to form chloral hydrate.

(b) the base-catalyzed hydration of acetone to form acetone hydrate

Show how you would synthesize the following derivatives from appropriate carbonyl compounds
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