ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 17, Problem 35P
Interpretation Introduction

Interpretation:

The stereochemical configuration of the propranolol formed by the given sequence is to be stated.

Concept introduction:

Epoxides undergo nucleophilic ring opening reactions which are acid-catalyzed.

If the epoxide is unsymmetrical, then the anionic nucleophile will attack the less-hindered carbon atom of the ring.

If the reaction conditions are acidic, then the reaction will occur at the more substituted carbon atom.

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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+

Chapter 17 Solutions

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