Chapter 19: Q21P (page 639)
Treatment of 2-cyclohexenone with HCN/KCN yields a saturated keto nitrile rather than an unsaturated cyanohydrin. Show the structure of the product,
and propose a mechanism for the reaction.
Short Answer

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Chapter 19: Q21P (page 639)
Treatment of 2-cyclohexenone with HCN/KCN yields a saturated keto nitrile rather than an unsaturated cyanohydrin. Show the structure of the product,
and propose a mechanism for the reaction.

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Draw and name the seven aldehydes and ketones with the formula . Which are chiral?
Give IUPAC names for the following compounds:
(a)

(b)

(c)

(d)

(e)

(f)

Ketones react with dimethylsulfonium methylide to yield epoxides. Suggest a mechanism for the reaction.

What carbonyl compound and what phosphorus ylide might you use to prepare each of the following compounds?
(a)

(b)

(c)

(d)

(e)

(f)

When crystals of pure -glucose are dissolved in water, isomerization occurs slowly to produce -glucose. Propose a mechanism for isomerization.

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