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Chapter 13: Carbonyl Compounds III: Reactions at the α-Carbon
Quizzes
Quiz 1
Quiz 1
This activity contains 11 questions.
What is the approximate p
K
a
of the α-carbon between a ketone carbonyl group and an ester carbonyl group of a β-keto ester?
-5
0
+5
+10
+50
What is the p
K
a
of the α-carbon of an ester?
10
40
5
25
15
Which of the following compounds is the most acidic?
propanenitrile
ethyl acetate
ethyl acetoacetate
2,4-pentanedione
acetone
The p
K
a
of the methylene group of 2,4-pentanedione, CH
3
-C(=O)-CH
2
-C(=O)-CH
3
is 8.9. Which statement best describes the charge distribution in the anion formed by deprotonation?
The negative charge is delocalized onto one of the carbonyl oxygens and most of the charge resides on that carbonyl oxygen.
The negative charge is delocalized onto both of the carbonyl oxygens and most of the charge resides on the two carbonyl oxygens.
The negative charge is delocalized onto one of the carbonyl oxygens and is shared equally between the CH carbon and one carbonyl oxygen.
The negative charge is localized on the carbon of the central CH group.
The negative charge is delocalized onto both of the carbonyl oxygens and is shared equally by the CH-carbon and the two carbonyl oxygens.
Which of the following is a true statement?
Acetone is more stable than its enol, and the p
K
a
of acetone is higher than the p
K
a
of the enol.
Acetone and its enol are equally stable, and the p
K
a
of acetone is lower than the p
K
a
of the enol.
Acetone is more stable than its enol, and the p
K
a
of acetone is lower than the p
K
a
of the enol.
Acetone is less stable than its enol, and the p
K
a
of acetone is lower than the p
K
a
of the enol.
Acetone is less stable than its enol, and the p
K
a
of acetone is higher than the p
K
a
of the enol.
Which of the following statements is
not
true about base-catalyzed alpha-substitution reactions?
Most of the anion's negative charge is located on the alpha-carbon.
The enolate ion resonance contributor predominates.
The base removes a proton from an alpha-carbon.
The anion formed is an ambident anion.
The intermediate formed in the reaction is a good nucleophile.
What product is formed when 3-pentanone is dissolved in D
2
O that contains some
-
OD?
CH
3
CD
2
-C(=O)-CD
2
CH
3
CH
3
CHD-C(=O)-CH
2
CH
3
CD
3
CD
2
-C(=O)-CD
2
CD
3
CH
3
CD
2
-C(=O)-CH
2
CH
3
CH
3
CHD-C(=O)-CHDCH
3
What product is formed when acetone undergoes an aldol condensation?
2-methyl-2,4-pentanediol
4-methyl-3-penten-2-one
4-methyl-4-penten-2-one
2,4-pentanedione
3-methyl-3-penten-2-one
The product of a Claisen condensation is
an alpha,beta-unsaturated aldehyde.
an alpha,beta-unsaturated ester.
an ester.
a beta-keto ester.
a beta-hydroxyester.
Which of the following steps does
not
occur in an acid-catalyzed alpha-substitution reaction?
proton abstraction from the alpha-carbon of the protonated carbonyl compound
nucleophilic addition to the C=C double bond of the enol
protonation of the carbonyl oxygen
addition of an electrophile to the alpha-carbon of the enol
loss of a proton from a protonated carbonyl group
Acetophenone, Ph-C(=O)-CH
3
, undergoes an aldol condensation when treated with sodium hydroxide. Explain why water is lost even if the initially formed addition product is not heated.
The C=C double bond and the carbonyl group are conjugated with each other.
Both benzenes rings and the C=C double bond are conjugated with each other.
One benzene ring is conjugated with a double bond.
One benzene is conjugated with a carbonyl group.
A benzene ring, the C=C double bond, and the carbonyl group are conjugated with each other.
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