Chapter 19: Q30E (page 648)
Predict the product(s) and provide the mechanism for each reactionbelow. What does each mechanism have in common?



Short Answer
(a)

(b)

(c)

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Chapter 19: Q30E (page 648)
Predict the product(s) and provide the mechanism for each reactionbelow. What does each mechanism have in common?



(a)

(b)

(c)

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Compound B is isomeric with A (Problem 19-79) and shows an IR peak at 1715 cm-1. The 1HNMR spectrum of B has peaks at 2.4 (1 H, septet, J = 7 Hz), 2.1 (3 H, singlet), and 1.2 (6 H, doublet, J =7 Hz). What is
the structure of B?
Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanonedoes not. Explain.
How might you use IR spectroscopy to determine whether reaction between2-cyclohexenoneand lithium dimethylcopper gives the direct addition productor the conjugate addition product?
Paraldehyde, a sedative, and hypnotic agent, is prepared by treatment of acetaldehyde with an acidic catalyst. Propose a mechanism for the reaction.

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