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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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Substitution vs. Elimination: Identify the major and minor

Chapter 8, Problem 8.77

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QUESTION:

Substitution vs. Elimination: Identify the major and minor product(s) for each of the following reactions: (a) Cl ? t-BuOK (b) OTs ? NaOH (c) OH ? conc. H2SO4 Heat (d) OTs ? NaCl DMSO (e) Br ? NaOEt (f) Br ? NaOEt (g) Br ? NaOEt EtOH (h) Br ? NaOEt EtOH (i) Br ? NaOEt EtOH (j) Br ? KOC(CH3) 3 (k) Br ? NaOMe (l) Cl ? NaO

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QUESTION:

Substitution vs. Elimination: Identify the major and minor product(s) for each of the following reactions: (a) Cl ? t-BuOK (b) OTs ? NaOH (c) OH ? conc. H2SO4 Heat (d) OTs ? NaCl DMSO (e) Br ? NaOEt (f) Br ? NaOEt (g) Br ? NaOEt EtOH (h) Br ? NaOEt EtOH (i) Br ? NaOEt EtOH (j) Br ? KOC(CH3) 3 (k) Br ? NaOMe (l) Cl ? NaO

ANSWER:

Step 1 of 13

The removal of the proton, the formation of the  bond, and the breaking of the bond to the leaving group are the three fundamental steps in an elimination process.

An  type of elimination reaction involves the formation of an intermediate and a two-step removal mechanism approach. This kind of reaction is referred to as a "unimolecular reaction."  reactions have first-order kinetics.

The nucleophilic elimination reaction that determines the rate of the  elimination has two components. Bond-forming and bond-breaking activities happen simultaneously in bimolecular  reactions.

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