ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 20, Problem 55DSP
Interpretation Introduction

Interpretation:

The reaction which occurs at the fastest rateis to be determined.

Concept Introduction:

The rate of nucleophilic acyl substitution is similar for thioesters and oxoesters.

When the nucleophile is an amine, thioesters are much more reactive than oxoesters.

The S-C=O is less stabilized than the O-C=O group.

Sulfur does not act as an electron pair donor to the oxygen and the carbonyl group.

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Predict the reactants used in the formation of the following compounds using Acid-Catalyzed dehydration reaction
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.. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show ll relevant stereochemistry [3 ONLY]. A H Br 1. NaCN 2 NaOH, H₂O, heat 3. H3O+ B. CH₂COOH 19000 1. LiAlH4 THF, heat 2 H₂O* C. CH Br 1. NaCN, acetone 2 H3O+, heat D. Br 1. Mg. ether 3. H₂O+ 2 CO₂ E. CN 1. (CH) CHMgBr, ether 2 H₂O+
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