ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
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Chapter 7.9, Problem 7.19E

(a)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromo-2-methylpropane with sodium iodide in acetone along with the dominant pathway adopted should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

(b)

Interpretation Introduction

Interpretation: The structure of major organic product that would result from reaction of 1-bromo-2-methylpropane with sodium ethoxide in ethanol along with the dominant pathway adopted should be written.

Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonated to yield small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, weak base waits until the carbocation is formed and the type of elimination with relatively weak base is two-step elimination or E1 .

Analogous to the case that strong nucleophiles are more favored to react via SN2 pathway, greater concentration of strong bases are more favored for single-step elimination E2 pathway. Such strong bases include hydroxide ion or alkoxide ions. The reason of predominance of E2 elimination is that strong bases have high probabilities and high rates to abstract hydrogen from carbon adjacent to carbocation.

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