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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Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

What Grignard reagent and what carbonyl compound might you startwith to prepare the following alcohols?
(a)
(b)
(c)
(d)
(e)
(f)
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.

What products would you expect to obtain from reaction of 1-methylcyclohexanol with the following reagents?
(a) HBr (b) NaH (c) H2SO4 (d) Na2Cr2O7
Question:Phenols generally have lower pKa’s than aliphatic alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the phenolate ions below. Make note of how the substituents either stabilize or destabilize the system.



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