Transcript 21_Test - Ventura College

Organic Chemistry, 6th edition
Paula Yurkanis Bruice
Chapter 21
More About Amines
Heterocyclic Compounds
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.1
Which of the following heterocyclic amines is aziridine?
A.
B.
HN
NH
C.
NH
D.
N
E.
NH
N
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.1
Which of the following heterocyclic amines is aziridine?
A.
B.
HN
NH
C.
NH
aziridine
azetidine
D.
pyrrolidine
N
E.
NH
piperidine
N
piperazine
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.1
Which is the correct name for the following
compound?
A.
B.
C.
D.
E.
N-ethyl-1-methylpiperidine
N-ethyl-3-methylpiperidine
N-ethyl-1-methylpyrrolidine
N-ethyl-3-methylpyrrolidine
N-ethyl-3-methylazetidine
N
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.1
Which is the correct name for the following
compound?
A.
B.
C.
D.
E.
N-ethyl-1-methylpiperidine
N-ethyl-3-methylpiperidine
N-ethyl-1-methylpyrrolidine
N-ethyl-3-methylpyrrolidine
N-ethyl-3-methylazetidine
N
The 6-membered heterocycle is a piperidine ring with
the nitrogen atom assigned as the 1-position.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.8
A.
Which of the following amines would you predict to
have the lowest pKa?
H3C
NH2
B.
C.
NH3
H
D.
N
H
H
E.
N
H
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
NH3
21.8
A.
Which of the following amines would you predict to
have the lowest pKa?
H3C
NH2
B.
pKa = 40
C.
NH3
pKa = 10.8
pKa = 4.5
H
D.
N
pKa = 5.6
H
H
E.
N
pKa = -2.4
NH3
H
Resonance
stabilization and loss
of aromaticity greatly
reduce nitrogen’s
basicity.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.8
Which compound is the product of the
bromination shown below?
A
C
B
Br
Br
Br2
N
H
1 equivalent
N
Br
N
H
Br
H
Br
N
H
Br
Br
N
H
D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
Br
N
H
E
21.8
Which compound is the product of the
bromination shown below?
A
C
B
Br
Br
Br2
N
H
1 equivalent
N
Br
N
H
Pyrrole, furan, and thiophene
undergo electrophilic
substitution preferentially at C-2
because the intermediates are
highly resonance stabilized.
Br
H
Br
N
H
Br
Br
N
H
D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
Br
N
H
E
21.9
Which set of reagents will accomplish the
following transformation in good yield?
?
N
A.
B.
C.
D.
E.
N
1. Br2/FeBr3; 2. PhLi
1. HBr; 2. Ph2CuLi
1. Br2, heat; 2. PhLi
1. Br2/FeBr3; 1. Ph2CuLi
Ph-Br/FeBr3
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.9
Which set of reagents will accomplish the
following transformation in good yield?
?
N
A.
B.
C.
D.
E.
1. Br2/FeBr3; 2. PhLi
1. HBr; 2. Ph2CuLi
1. Br2, heat; 2. PhLi
1. Br2/FeBr3; 1. Ph2CuLi
Ph-Br/FeBr3
N
Electrophilic substitution on
pyridine is facilitated at the
3-position but nucleophilic
substitution is not so a
Gillman reagent is needed.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.10 Which of the following heterocyclic amines is
pyrimidine?
A.
B. HN
NH
C.
N
N
D.
N
N
H
N
E. N
N
N
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
21.10 Which of the following heterocyclic amines is
pyrimidine?
A.
B. HN
NH
C.
N
N
pyrrole
D.
imidazole
N
N
pyrimidine
pyridine
H
N
E. N
N
N
purine
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.