24. Enolate Chemistry: Reactions at the Alpha-Carbon

Provide the major product for the following reaction

Provide the major product for the following reaction

Draw the products of the following reactions: e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H₂O + heat

Explain why the following carboxylic acids cannot be prepared by a malonic ester synthesis:

c.

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?

Amobarbital is a sedative marketed under the trade name Amytal. Propose a synthesis of amobarbital, using diethyl malonate and urea as two of the starting materials.

Show how the following compounds can be made using the malonic ester synthesis.

(a) 3-phenylpropanoic acid

(b) 2-methylpropanoic acid

Show how you would use the malonic ester synthesis to make the following compounds.

Show the structure of the compound that results from hydrolysis and decarboxylation of the product.

Show how the following compounds can be made using the malonic ester synthesis.

(c) 4-phenylbutanoic acid

(d) cyclopentanecarboxylic acid

What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids?

a. propanoic acid

b. 2-methylpropanoic acid

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step?

a.

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step?

b. CH₃SCH₂CH₂Br

Design a synthesis for each of the following compounds using the given starting material:

d.