ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Chapter 16, Problem 29P
Interpretation Introduction

Interpretation:

The reaction sequence for each of the given conversion required two synthetic steps with suitable reagents is to be suggested.

Concept introduction:

The ketone on reduction with sodium borohydride gives secondary alcohols.

The alcohol on dehydration in presence of acid catalyst eliminates water molecule and forms double bond.

The primary alcohols on oxidation with good oxidizing agent forms carboxylic acid.

The tertiary alcohol does not undergo oxidation to form carbonyl compound.

Vicinal diols on treatment with periodic acid (HIO4) undergoes cleavage of carbon-carbon bond of vicinal diol and results in two carbonyl compounds.

The dihydroxylation is the addition of two hydroxyl groups to the double bond of alkene to form a 1,2 diol. The both hydroxyl groups add to double bond from same side of double bond.

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A J то گای ه +0 Also calculate the amount of starting materials chlorobenzaldehyde and p-chloroacetophenone required to prepare 400 mg of the given chalcone product 1, 3-bis(4-chlorophenyl)prop-2-en-1-one molar mass ok 1,3-bis(4-Chlorophenyl) prop-2-en-1-one = 277.1591m01 number of moles= 0.400/277.15 = 0.00144 moles 2 x 0.00 144=0.00288 moves arams of acetophenone = 0.00144 X 120.16 = 0.1739 0.1739x2=0.3469 grams of benzaldehyde = 0.00144X106.12=0.1539 0.1539x2 = 0.3069 Starting materials: 0.3469 Ox acetophenone, 0.3069 of benzaldehyde 3

Chapter 16 Solutions

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