Transcript Chapter 18 Quiz - Ventura College

Organic Chemistry, 6th edition
Paula Yurkanis Bruice
Chapter 18
Carbonyl Compounds II
Reactions of Aldehydes and Ketones
More Reactions of Carboxylic Acid Derivatives
Reactions of α,β-Unsaturated Carbonyl Compounds
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.1
Which is the systematic name for the
following compound?
O
H
O
A. 3-methyl-4-oxopentanal
B. 3-methyl-2-oxopentanal
C. 3-methyl-2-oxo-5-pentanal
D. 3-methyl-5-oxo-2-pentanone
E. 3-methylpentan-5-one-1-al
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.1
Which is the systematic name for the
following compound?
O
4
5
O
3
2
1
H
A. 3-methyl-4-oxopentanal
B. 3-methyl-2-oxopentanal
C. 3-methyl-2-oxo-5-pentanal
D. 3-methyl-5-oxo-2-pentanone
E. 3-methylpentan-5-one-1-al
The aldehyde group has higher priority than the keto
group and is assigned the 1 position.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.2
Which is the correct order of decreasing
reactivity toward nucleophilic attack?
1.
2.
3.
4.
5.
Acyl halide
Aldehyde
Carboxylate ion
Carboxylic acid
Ketone
A.
B.
C.
D.
E.
1>2>3>4>5
1>2>5>4>3
1>5>2>4>3
2>5>1>3>4
5>2>1>3>4
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.2
Which is the correct order of decreasing
reactivity toward nucleophilic attack?
1.
2.
3.
4.
5.
Acyl halide
Aldehyde
Carboxylate ion
Carboxylic acid
Ketone
A.
B.
C.
D.
E.
1>2>3>4>5
1>2>5>4>3
1>5>2>4>3
2>5>1>3>4
5>2>1>3>4
Acid halides are the most reactive carboxylic acid derivative.
Aldehydes are more reactive than ketones since they are less
hindered and have only one donor group attached to the carbonyl.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.8
Which set of reagents would best accomplish
the transformation below?
O
N
?
+
A
H 2N
NH2
H+ cat.
B
NH
H+ cat.
C
NH
H+ cat. NH2NH2
D
NH
E
NH
H+ cat. NaBH4
H+ cat. NaBH(OAc)3
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.8
Which set of reagents would best accomplish
the transformation below?
O
N
?
+
A
H 2N
NH2
H+ cat.
B
NH
H+ cat.
C
NH
H+ cat. NH2NH2
D
NH
E
NH
H+ cat. NaBH4
H+ cat. NaBH(OAc)3
This is an enamine synthesis
commonly used in the Stork reaction.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.10 The role of an acid catalyst in the formation of
a ketal is to_____.
A. protonate the C=O making it a better electrophile
B. protonate the C=O making it more reactive toward
weak nucleophiles such as alcohols
C. protonate the tetrahedral hemiketal which facilitates
loss of water
D. force the equilibrium of the reaction to the right
E. All of the above
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.10 The role of an acid catalyst in the formation of
a ketal is to_____.
A. protonate the C=O making it a better electrophile
B. protonate the C=O making it more reactive toward
weak nucleophiles such as alcohols
C. protonate the tetrahedral hemiketal which facilitates
loss of water
D. force the equilibrium of the reaction to the right
E. All of the above
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.13 Which of the following alkenes could not be
prepared from cyclohexanone using the
Witting reaction?
A
B
D
C
E
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.13 Which of the following alkenes could not be
prepared from cyclohexanone using the
Witting reaction?
A
B
D
C
E
The Wittig reagent needed for this alkene cannot be
prepared from the highly hindered neopentyl halide.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
18.16 Which compound is the product of the
following sequence of reactions?
O
A
OH
-CN,
HCl
HCl, heat
OH
OH
B
NaBH4, CeCl3
C
CH2NH2
OH
D
OH
E
CO2H
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
CO2H
18.16 Which compound is the product of the
following sequence of reactions?
O
A
OH
-CN,
HCl
HCl, heat
OH
OH
B
NaBH4, CeCl3
C
CH2NH2
OH
D
OH
E
CO2H
CO2H
1,4-addition of the nitrile followed by hydrolysis gives a
saturated keto acid. NaBH4 (CeCl3 not necessary) reduces
only the ketone.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.