Transcript Chapter 19 Quiz - Ventura College
Organic Chemistry, 6 th edition Paula Yurkanis Bruice
Chapter 19 Carbonyl Compounds III
Reactions at the
α
-Carbon
Brian L. Groh Minnesota State University, Mankato Mankato, MN
Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.1
1 O
Which is the correct order of
decreasing
acidity (increasing p
K
a )?
O O O 2 3 4 H 3 C H H 3 C C H 3 H 3 C C H 2 CH 3 CH 3 C H 2 CN 5 CH 3 C H 3
A. 4 > 3 > 2 > 1 > 5 B. 3 > 2 > 1 > 4 > 5 C. 5 > 4 > 2 > 1 > 3 D. 1 > 2 > 3 > 4 > 5 E. 3 > 1 > 2 > 4 > 5 Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.1
1 O
Which is the correct order of
decreasing
acidity (increasing p
K
a )?
O O O 2 3 4 H 3 C H H 3 C C H 3 H 3 C C H 2 CH 3 CH 3 C H 2 CN
p
K
a = 17 20 9 26 A. 4 > 3 > 2 > 1 > 5 D. 1 > 2 > 3 > 4 > 5 B. 3 > 2 > 1 > 4 > 5 E. 3 > 1 > 2 > 4 > 5 C. 5 > 4 > 2 > 1 > 3 The most acidic hydrogens form the most highly stabilized conjugate bases.
5 CH 3 C H 3
45 Bruice:
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19.5
A O O
Which compound is the likely starting material for the reaction shown below?
B O 1. H + , Br 2 O O 2. CH 3 O , CH 3 OH OH O C O D H E O
Bruice:
Organic Chemistry
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19.5
A O O
Which compound is the likely starting material for the reaction shown below?
B O 1. H + , Br 2 O O 2. CH 3 O , CH 3 OH OH O C E O O D H
Addition of Br 2 to
E
under acidic conditions gives an alpha-bromoketone which undergoes nucleophilic substitution by CH 3 O
-
to give the observed product. Bruice:
Organic Chemistry
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19.10
Which of the following reactions will fail to give the desired product?
?
O O A. 1. LDA 2. CH 3 Br B. 1. Br 2 , H 3 O + 2. CH 3 Li C. 1. (CH 3 ) 2 NNH 2 2. BuLi 3. CH 3 Br 4. HCl/H 2 O D. 1.
NH H + cat.
2. CH 3 Br 3. HCl/H 2 O E. 1.
2. CH 3 Br N Li
Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.10
Which of the following reactions will fail to give the desired product?
?
O O A. 1. LDA 2. CH 3 Br B. 1. Br 2 , H 3 O + 2. CH 3 Li
Methyllithium will react with the carbonyl group.
C. 1. (CH 3 ) 2 NNH 2 2. BuLi 3. CH 3 Br 4. HCl/H 2 O D. 1.
NH H + cat.
2. CH 3 Br 3. HCl/H 2 O E. 1.
2. CH 3 Br N Li
Bruice:
Organic Chemistry
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19.18
O +
What is the major product of the following reaction?
A B O HO O O heat O O O O OH C D E OH
Bruice:
Organic Chemistry
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19.18
O +
What is the major product of the following reaction?
A B O HO O O heat O O O O OH C D E OH
This is a Robinson annulation reaction. Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.12 19.21
What type of reaction was most likely used to prepare the following compound?
O O O O ?
+ Br Br
A. Aldol condensation B. Acetoacetic ester synthesis C. Claisen condensation D. Malonic ester synthesis E. Robinson annulation Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.12 19.21
What type of reaction was most likely used to prepare the following compound?
O O 1. base 2. H 3 O + , heat O O + Br Br
Alkylation followed by hydrolysis and decarboxyla tion gives the product. A. Aldol condensation B. Acetoacetic ester synthesis C. Claisen condensation D. Malonic ester synthesis E. Robinson annulation Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.12 19.21
What type of reaction was most likely used to prepare the following compound?
CHO O OCH 2 CH 3 O ?
+ OCH 2 CH 3 H OCH 2 CH 3 O
A. Aldol condensation B. Acetoacetic ester synthesis C. Mixed Claisen condensation D. Malonic ester synthesis E. Robinson annulation Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.
19.12 19.21
What type of reaction was most likely used to prepare the following compound?
OCH 2 CH 3 1. CH 3 CH 2 O 2. H 3 O + CHO OCH 2 CH 3 O + O H OCH 2 CH 3
Mixed Claisen condensations work best when only one partner has acidic hydrogens.
O
A. Aldol condensation B. Acetoacetic ester synthesis C. Mixed Claisen condensation D. Malonic ester synthesis E. Robinson annulation Bruice:
Organic Chemistry
, © 2011 Pearson Education, Inc.