Give the structure of the principal organic product formed on reaction of benzyl bromide with each of the following reagents:
(a) Sodium ethoxide
(b) Potassium tert-butoxide
(c) Sodium azide
(d) Sodium hydrogen sulfide
(e) Sodium iodide (in acetone)
Sample Solution (a) Benzyl bromide is a primary bromide and undergoes SN2 reactions readily. It has no hydrogens β to the leaving group and so cannot undergo elimination. Ethoxide ion acts as a nucleophile, displacing bromide and forming benzyl ethyl ether.
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