Chapter 17: Q22E (page 567)
Predict the product from reaction of the following substance (reddish brown=Br) with:
(a)
(b) Aqueous
(c)
(d)Dess-Martin periodinane
(e)

Short Answer

(a)

(b)

(c)

(d)

(e)
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Chapter 17: Q22E (page 567)
Predict the product from reaction of the following substance (reddish brown=Br) with:
(a)
(b) Aqueous
(c)
(d)Dess-Martin periodinane
(e)


(a)

(b)

(c)

(d)

(e)
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Predict the product from reaction of the following substance with:
3. ; then

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

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.

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

Question: How would you prepare the following compounds from
2-phenylethanol?
More than one step may be required.
(a) Styrene
(b) Phenylacetaldehyde
(c) Phenylacetic acid
(d) Benzoic acid
(e) Ethylbenzene
(f) Benzaldehyde
(g) 1-Phenylethanol
(h) 1-Bromo-2-phenylethane
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