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Chapter 13: Carbonyl Compounds III: Reactions at the α-Carbon
Exercises
Practice Exercise 3
Practice Exercise 3
This activity contains 5 questions.
What is the main reason that a hydrogen bonded to a carbon adjacent to a carbonyl carbon is more acidic than a hydrogen of an alkane?
The carbonyl group is an electron-withdrawing group and weakens the C-H bond in the alpha-position.
The negative charge is delocalized, and most of the charge resides on the alpha-carbon.
The negative charge is stabilized by its proximity to the negatively charged carbonyl carbon.
The carbonyl group is an electron-donating group and weakens the C-H bond in the alpha-position.
The negative charge is delocalized, and most of the charge resides on the electronegative carbonyl oxygen.
Which of the following compounds has the lowest p
K
a
?
CH
3
-CN
CH
3
-C(=O)-CH
2
-C(=O)-OCH
3
CH
3
-C(=O)-CH
2
-C(=O)-CH
3
CH
3
-C(=O)-CH
3
CH
3
-C(=O)-N(CH
3
)
2
Which statement best describes keto-enol interconversion?
It is always an acid-catalyzed reaction.
It can be either an acid-catalyzed or a base-catalyzed reaction.
It is always a base-catalyzed reaction.
The reaction is not affected by catalysts.
An alkyl halide can be used to alkylate an enalote ion. What kind of reaction is this?
a bimolecular nucleophilic addition
a unimolecular nucleophilic substitution
a unimolecular electrophilic substitution
a bimolecular nucleophilic substitution
a bimolecular electrophilic substitution
For which of the following compounds would the enol tautomer predominate in aqueous solution?
ethyl 3-oxobutanoate
1,3-cyclohexanedione
phenol
cyclohexanone
2,4-pentanedione
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