ORGANIC CHEMISTRY - CONNECT ACCESS CARD
ORGANIC CHEMISTRY - CONNECT ACCESS CARD
10th Edition
ISBN: 9781259636394
Author: Carey
Publisher: MCG
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Chapter 23, Problem 18P
Interpretation Introduction

Interpretation: The compound A in the given synthesis of the analogs of anthracycline antibiotics is to be identified.

Concept introduction:

The reaction that involves the rearrangement of the esters of phenol into a hydroxyl aryl ketone with the use of Lewis acid catalyst is called as Fries rearrangement reaction.

The relocation of the phenol ester acyl group to the aryl ring takes place in this type of reaction.

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16. When cis-1,2-cyclopentanediol reacts with acetone in dry HCl, compound M is formed. What do you expect the hydrolysis of compound M to be when subjected (i) to base; and, (ii) acid A. resistant to base; resistant to acid B. resistant to base; readily hydrolyzed by acid C. readily hydrolyzed by base; resistant to acid D. readily hydrolyzed by base; readily hydorlyzed by acid
16. When cis-1,2-cyclopentanediol reacts with acetone in dry HCl, compound M is formed. What do you expect the hydrolysis of compound M to be when subjected (i) to base; and, (ii) acid   a. resistant to base; resistant to acid b. resistant to base; readily hydrolyzed by acid c. readily hydrolyzed by base; resistant to acid d. readily hydrolyzed by base; readily hydorlyzed by acid   17. Following (16), would you expect that a similar compound be formed if the reactant was trans-1,2-cyclopentanediol? Why is this so?   a. Yes; hydroxyl groups are on opposite side b. No; hydroxyl groups are on opposite site c. Yes; hydroxyl groups are on the same side d. No; hydroxyl groups are on the same side
Shown below is the 1H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form acompound with molecular formula C11H14. What product is obtained from the Wittig reaction?
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