Transcript Chapter 17 Quiz - Ventura College

Organic Chemistry, 6th edition
Paula Yurkanis Bruice
Chapter 17
Carbonyl Compounds I
Reactions of Carboxylic Acids and
Carboxylic Derivatives
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.2
Which of the following compounds is
propanoic anhydride?
A
O
D
O
O
O
B
O
O
O
O
O
O
E
O
O
O
C
O
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
O
17.2
Which of the following compounds is
propanoic anhydride?
A
O
D
O
O
O
B
O
O
O
O
O
O
E
O
O
O
C
O
O
Propanoic anhydride is
made of two 3-carbon acids.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.6
Which carboxylic acid derivative is most
readily hydrolyzed by aqueous base?
O
O
A
H 3C
C
N
CH3
B
CH3
H 3C
C
O
C
H 3C
C
Cl
O
OCH2CH3
D
H3CH 2C
C
O
O
C
E Carboxylic acid derivatives hydrolyze by the same
mechanism and at the same approximate rate.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
CH2CH3
17.6
Which carboxylic acid derivative is most
readily hydrolyzed by aqueous base?
O
O
A
H 3C
C
N
CH3
B
CH3
H 3C
C
O
C
H 3C
C
Best leaving
group = fastest
hydrolysis
Cl
O
OCH2CH3
D
H3CH 2C
C
O
O
C
E Carboxylic acid derivatives hydrolyze by the same
mechanism and at the same approximate rate.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
CH2CH3
17.7
Under basic conditions, in nucleophilic acyl
substitution, _____.
A. protonation of the carbonyl group is
followed by nucleophilic attack
B. loss of the leaving group is followed by
formation of an acylium ion
C. an SN2 mechanism is followed
D. the nucleophile must be a weaker base
than the leaving group
E. nucleophilic addition to the carbonyl is
followed by loss of a leaving group
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.7
Under basic conditions, in nucleophilic acyl
substitution, _____.
A. protonation of the carbonyl group is
followed by nucleophilic attack
B. loss of the leaving group is followed by
formation of an acylium ion
C. an SN2 mechanism is followed
D. the nucleophile must be a weaker base
than the leaving group
E. nucleophilic addition to the carbonyl is
followed by loss of a leaving group
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
Protonation
doesn’t
occur under
basic
conditions.
17.10 Which of the following carboxylic acid
derivatives could be used in this reaction?
O
O
X
For X =
A.
B.
C.
D.
E.
(CH3CH2)2NH
N(CH2CH3)2
-Br
-Cl
-OC(=O)CH3
-OCH3
Any of the above
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.10 Which of the following carboxylic acid
derivatives could be used in this reaction?
O
O
X
For X =
A.
B.
C.
D.
E.
(CH3CH2)2NH
-Br
-Cl
-OC(=O)CH3
-OCH3
Any of the above
N(CH2CH3)2
All of these derivatives
are more reactive than
the amide product.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.13 Upon aqueous hydrolysis of 18O labeled ethyl acetate,
which oxygen(s) will be labeled in the final reaction
mixture after mild acidification?
18
O
H 3C
C
HO
18
OCH 2CH3
-
A
H 3C
H 3C
H 3C
OH
B
H 3C
OH
D
CH3CH218OH
C
18
OH
O
C
18
E
O
C
18
C
O
18
O
C
18
OH
and
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
CH 3CH218OH
17.13 Upon aqueous hydrolysis of 18O labeled ethyl acetate,
which oxygen(s) will be labeled in the final reaction
mixture after mild acidification?
18
O
H 3C
C
HO
18
-
OCH 2CH3
A
H 3C
C
H 3C
H 3C
OH
B
H 3C
OH
D
CH3CH218OH
C
18
OH
O
C
18
E
O
C
18
Nucleophilic attack by
hydroxide occurs at the
acyl group resulting in
loss of the 18O labeled
ethoxy group.
O
18
O
C
18
OH
and
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
CH 3CH218OH
17.21 Which compound is the product of the reaction
sequence?
O
OH
SOCl2
(CH3CH 2)2NH
CH3OH
HOH
H + catalyst
O
A
O
Cl
HO
B
O
D
O
O
OH
C
OH
O
OCH3
E
N(CH 2CH3)2
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
17.21 Which compound is the product of the reaction
sequence?
O
OH
SOCl2
(CH3CH 2)2NH
CH3OH
HOH
H + catalyst
O
A
O
Cl
HO
B
O
D
O
O
OH
C
O
OCH3
E
N(CH 2CH3)2
OH
Acid => acid
chloride => ester
=> amide, which
is stable toward
reaction with
water.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.