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Problem 28a
Draw the products of the following reactions:
a.
Problem 28b
Draw the products of the following reactions:
b.
Problem 29a
Which of the following esters cannot undergo a Claisen condensation?
Problem 31c
Show how each of the following compounds can be prepared from methyl phenyl ketone:
c.
Problem 32
Write the mechanism for the reaction of a 1,7-diester with an alkoxide ion to form a cyclic b-keto ester.
Problem 34
Can 2,4-pentanedione undergo an intramolecular aldol addition? If so, why? If not, why not?
Problem 35a
Draw the product of the reaction of each of the following compounds with a base:
a.
Problem 35b
Draw the product of the reaction of each of the following compounds with a base:
b.
Problem 35c
Draw the product of the reaction of each of the following compounds with a base:
c.
Problem 35d
Draw the product of the reaction of each of the following compounds with a base:
d.
Problem 36a
Draw the product obtained by heating each pair of ketones in a basic solution.
a.
Problem 36b
Draw the product obtained by heating each pair of ketones in a basic solution.
b.
Problem 37a
What two carbonyl compounds are needed to synthesize each of the following compounds, using a Robinson annulation?
a.
Problem 38a,b
Which of the following compounds will decarboxylate when heated?
a.
b.
Problem 38c,d,e
Which of the following compounds will decarboxylate when heated?
Problem 39a,b
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
Problem 40c
Explain why the following carboxylic acids cannot be prepared by a malonic ester synthesis:
c.
Problem 41a
What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? a. 2-pentanone
Problem 41b
What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? b. 2-octanone
Problem 41c
What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones? c. 4-phenyl-2-butanone
Problem 43b
Design a synthesis for each of the following compounds using the given starting material:
b.
Problem 43d
Design a synthesis for each of the following compounds using the given starting material:
d.
Problem 48a
Draw a structure for each of the following:
a. ethyl acetoacetate
Problem 48b
Draw a structure for each of the following:
b. a-methylmalonic acid
Problem 48c
Draw a structure for each of the following:
c. a β-keto ester
Problem 48d
Draw a structure for each of the following: d. the enol tautomer of cyclopentanone
Problem 49a
Draw the products of the following reactions:
a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl
Problem 49b
Draw the products of the following reactions: b. pentanoic acid + PBr3 + Br2, followed by hydrolysis
Problem 49c
Draw the products of the following reactions:
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl
Problem 49e
Draw the products of the following reactions: e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + heat
