Chapter 17: Q43E (page 567)
What carbonyl compounds would you reduce to prepare the followingalcohols? List all possibilities.
(a)
(b)
(c)
Short Answer
(a)




(b)

(c)
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Chapter 17: Q43E (page 567)
What carbonyl compounds would you reduce to prepare the followingalcohols? List all possibilities.
(a)
(b)
(c)
(a)




(b)

(c)
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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)
The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.

Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction.

Question: Give IUPAC names for the following compounds:






Compound A, , has the IR and NMR spectra shown. Proposea structure consistent with the observed spectra, and label each peak inthe NMR spectrum. Note that the absorption at disappears when is added.

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