ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 25, Problem 27P
Interpretation Introduction

Interpretation:

A mechanism is to be proposed for the given transformation which was carried out as a part of a multistep synthesis of digitoxigenin.

Concept Introduction:

Hydroxyl group is not a good leaving group.

In the presence of an acid, the hydroxyl group gets protonated and is converted to a good leaving group.

A carbocation is formed when the leaving group departs. Resonance of the positive charge stabilizes the carbocation.

Addition of water to the carbocation results in further reaction and deprotonation.

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6. Consider the following exothermic reaction below. 2Cu2+(aq) +41 (aq)2Cul(s) + 12(aq) a. If Cul is added, there will be a shift left/shift right/no shift (circle one). b. If Cu2+ is added, there will be a shift left/shift right/no shift (circle one). c. If a solution of AgNO3 is added, there will be a shift left/shift right/no shift (circle one). d. If the solvent hexane (C6H14) is added, there will be a shift left/shift right/no shift (circle one). Hint: one of the reaction species is more soluble in hexane than in water. e. If the reaction is cooled, there will be a shift left/shift right/no shift (circle one). f. Which of the changes above will change the equilibrium constant, K?
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