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Chapter 13: Carbonyl Compounds III: Reactions at the α-Carbon
Quizzes
Quiz 2
Quiz 2
This activity contains 11 questions.
Which of the following compounds will be most apt to undergo decarboxylation when it is heated?
CH
3
CH
2
CH
2
-COOH
CH
3
-C(=O)-CH
2
-COOH
CH
3
-C(=O)-COOH
CH
3
-C(=O)-CH
2
CH
2
-COOH
CH
3
-C(=O)-CH
2
CH
2
CH
2
-COOH
(CH
3
)
2
C=CH-C(=O)-CH
3
can be prepared by an aldol condensation. Identify the reactant and the reaction conditions.
acetone, hydroxide ion, heat
acetone, hydroxide ion
acetaldehyde, hydroxide ion
acetaldehyde, hydroxide ion, heat
propanal, hydroxide ion, heat
What is the molecular formula of the compound obtained when the product of an aldol condensation of butanal is catalytically hydrogenated?
C
8
H
18
O
C
8
H
16
O
2
C
4
H
8
O
C
8
H
16
O
2
C
8
H
14
O
What is being "condensed off" when methyl propanoate undergoes a Claisen condensation?
CH
3
OH
CH
3
CH
2
COOH
H
2
O
CH
3
COOH
CH
3
CH
2
OH
What product is formed when 1-bromobutane is used in an acetoacetic ester synthesis?
2-pentanone
hexanoic acid
heptanoic acid
2-heptanone
2-hexanone
Which of the following is
not
true about keto-enol interconversion of a ketone such as 2,4-pentanedione?
At equilibrium there will be more of the keto tautomer than the enol tautomer.
A proton is donated to the oxygen atom.
A proton is removed from the methylene carbon of the ketone.
An enolate ion is formed as an intermediate in the acid-catalyzed reaction.
An enolate ion is formed as an intermediate in the base-catalyzed reaction.
What carboxylic acid will be formed from the malonic ester synthesis when 1-bromopropane is used as the alkylating reagent?
CH
3
CH
2
COOH
CH
3
CH
2
CH
2
CH
2
CH
2
COOH
CH
3
CH
2
CH
2
CH
2
COOH
CH
3
COOH
CH
3
CH
2
CH
2
COOH
Identify the correct sequence of reagents employed in an acetoacetic ester synthesis.
(1) warm acid-catalyzed hydrolysis (2) alkoxide ion (3) alkyl bromide
(1) alkyl bromide (2) alkoxide ion (3) warm acid-catalyzed hydrolysis
(1) alkoxide ion (2) warm acid-catalyzed hydrolysis (3) alkyl bromide
1) alkyl bromide (2) warm acid-catalyzed hydrolysis (3) alkoxide ion
(1) alkoxide ion (2) alkyl bromide (3) warm acid-catalyzed hydrolysis
Which of the following is
not
a true statement?
Ketones are stronger acids than esters.
Acid-catalyzed hydrolysis of a β-hydroxyaldehyde forms a non-conjugated double bond.
Butyl bromide is the alkyl halide required for the synthesis of hexanoic acid via the malonic ester synthesis.
The acetoacetic ester synthesis leads to the formation of methyl ketones.
The product of a Claisen condensation is a beta-keto ester.
What product is formed when 2-methylcyclohexanone reacts with a strong base and the resulting enolate is alkylated with ethyl bromide?
2-ethyl-6-methylcyclohexanone
5-ethyl-2-methylcyclohexanone
3-ethyl-2-methylcyclohexanone
2-ethyl-2-methylcyclohexanone
4-ethyl-2-methylcyclohexanone
What size ring is formed when 2,5-hexanedione undergoes an aldol addition?
2
4
5
6
7
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