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Predict the major products of the following reactions. (a) ethyl tosylate + potassium
Chapter 11, Problem PROBLEM 11-9(choose chapter or problem)
Predict the major products of the following reactions.
(a) ethyl tosylate + potassium tert-butoxide
(b) isobutyl tosylate + NaI
(c) (R)-2-hexyl tosylate + NaCN
(d) the tosylate of cyclohexylmethanol + excess \(\mathrm{NH}_{3}\)
(e) n-butyl tosylate + sodium acetylide, \(\mathrm{H}-\mathrm{C} \equiv \mathrm{C}:{ }^{-+} \mathrm{Na}\)
Questions & Answers
QUESTION:
Predict the major products of the following reactions.
(a) ethyl tosylate + potassium tert-butoxide
(b) isobutyl tosylate + NaI
(c) (R)-2-hexyl tosylate + NaCN
(d) the tosylate of cyclohexylmethanol + excess \(\mathrm{NH}_{3}\)
(e) n-butyl tosylate + sodium acetylide, \(\mathrm{H}-\mathrm{C} \equiv \mathrm{C}:{ }^{-+} \mathrm{Na}\)
ANSWER:Step 1 of 5
(a) Ethyl tosylate reacts with potassium tert-butoxide to generate two products. At high temperatures, the product obtained is ethene and the reaction is a substitution reaction which can be given as:
At low temperatures, the product obtained is 2-ethoxy-2-methylpropane and the reaction is an elimination reaction which can be given as: