Chapter 17: Q16P (page 814)
How could each of the following compounds be prepared from cyclohexanone?
a.

b.

c.

Short Answer
a.

b.

c.

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Chapter 17: Q16P (page 814)
How could each of the following compounds be prepared from cyclohexanone?
a.

b.

c.

a.

b.

c.

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a. What carboxylic acid is formed when the malonic ester synthesis is carried out with one equivalent of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?
b. What carboxylic acid is formed when the malonic ester synthesis is carried out with two equivalents of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?
What compound is formed when a dilute solution of cyclohexanone is shaken with NaOD in for several hours?
The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an ß-bromo ester with zinc.
Describe how each of the following compounds can be prepared, using a Reformatsky reaction:
What two carbonyl compounds are required for the synthesis of morachalcone A (the aromatase inhibitor discussed in the box below), via a Claisen–Schmidt condensation?
Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.
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