ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
10th Edition
ISBN: 9781259917196
Author: Carey
Publisher: MCG CUSTOM
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Chapter 17.14, Problem 17P
Interpretation Introduction

Interpretation:

The structure and the stereochemistry along with the description of the configuration of each of the chiral centers present in the given product areto be determined.

Concept Introduction:

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The compounds of the type R-S-R' are known as sulfides.

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They are synthesized by the nucleophilic substitution reactions.

>

The reaction between primary or secondary alkyl halides with alkanethiolate ion results in the formation of sulfides.

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(a) What is the structure of C, which is formed by oxy-Cope rearrangement of B with NaOEt? (b) Draw a stepwise mechanism for the conversion of C to the bicyclic alcohol D.
An allylic alcohol contains an OH group on a carbon atom adjacent to aC—C double bond. Treatment of allylic alcohol A with HCl forms amixture of two allylic chlorides, B and C. Draw a stepwise mechanismthat illustrates how both products are formed.
(a) Give an acceptable name for compound A. (b) Draw the organic products formed when A is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.

Chapter 17 Solutions

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