Chapter 17: Q11P (page 543)
Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:

Short Answer
The reaction of cyclohexanone with Grignard reagent is shown as,

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Chapter 17: Q11P (page 543)
Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following compound:

The reaction of cyclohexanone with Grignard reagent is shown as,

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p-Nitrobenzyl alcohol is more acidic than benzyl alcohol, but p-methoxy-benzyl alcohol is less acidic. Explain.
How would you synthesize the following alcohols, starting with benzene and other alcohols of six or fewer carbons as your only organic reagents?
(a)

(b)

(c)

(d)

Benzoquinone is an excellent dienophile in the Diels – Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3 butadiene? From reaction with 2 equivalents of 1,3 butadiene?
Question:The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:
(a) tert-butyldimethylsilyl chloride (TBS-Cl)
(b) triisopropylsilyl chloride (TIPS-Cl)
(c) triethylsilyl chloride (TES-Cl)
What alcohols would give the following products on oxidation?
(a)

(b)

(c)

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