Predict the products of the following reactions.(a) CH3CH2CH2CH2C‚N + CH3CH2MgBr, then H3O+(b) CH3CH2CH2CH2C‚N + DIBAL-H, then H3O+(c) benzyl bromide + sodium cyanide(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis(e) product of (c) + DIBAL-H, then hydrolysis

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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Predict the products of the following reactions.
(a) CH3CH2CH2CH2C‚N + CH3CH2MgBr, then H3O+
(b) CH3CH2CH2CH2C‚N + DIBAL-H, then H3O+
(c) benzyl bromide + sodium cyanide
(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis
(e) product of (c) + DIBAL-H, then hydrolysis

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