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Organic Chemistry, 6th edition
Paula Yurkanis Bruice
Chapter 10
Reactions of Alcohols, Amines,
Ethers, Epoxides, and SulfurContaining Compounds
Brian L. Groh
Minnesota State University, Mankato
Mankato, MN
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.4
Which alkene is the major product of this
dehydration?
A
OH
C
B
H2SO4
heat
D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
E
10.4
Which alkene is the major product of this
dehydration?
A
OH
C
B
H2SO4
heat
Acid catalyzed dehydration
generally gives the most stable
alkene.
D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
E
10.4
Which alkene is the major product of this
dehydration?
OH
A
B
H2SO4
heat
E
C
D
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
A, B & C
10.4
Which alkene is the major product of this
dehydration?
OH
A
B
H2SO4
heat
E
C
D
A, B & C
SN conditions favor rearrangement of the carbocation
intermediate. Only small amounts of A and B will form.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.5
Which alcohol will not be oxidized by chromic
acid?
A
B
C
OH
OH
OH
O
OH
D
OH
E
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.5
Which alcohol will not be oxidized by chromic
acid?
A
B
C
OH
OH
OH
O
OH
D
OH
E
Tertiary alcohols will not
be oxidized with chromic
acid.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.6
What is the major product of this reaction?
A
B
1 mol HI
O
I
I
C
HO
OH
I
I
D
I
I
E
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.6
What is the major product of this reaction?
A
B
1 mol HI
O
I
I
C
HO
OH
I
I
D
I
I
E
Protonation of the oxygen will be followed by nucleophilic
attack by I- at the least hindered carbon.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.7
What is the major product of this reaction?
A
H
B
OCH3
+
OCH3
O
CH3OH
OH
OH
OH
OH
C
A&B
OCH3
D
OCH3
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
E
10.7
What is the major product of this reaction?
A
H
B
OCH3
+
OCH3
O
CH3OH
OH
OH
OH
OH
C
A&B
OCH3
D
OCH3
E
Under acidic conditions the alcohol attacks the more
electrophilic tertiary carbon of the protonated epoxide.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.9
What is the major product of the following
reaction?
1. CH3I (excess)/K2CO3
2. Ag2O, H2O
N
H
A
B
N
3. heat
C
N
D
N
E
N
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
10.9
What is the major product of the following
reaction?
1. CH3I (excess)/K2CO3
2. Ag2O, H2O
N
H
A
B
N
3. heat
C
This is the Hoffman elimination
which favors formation of the
least substituted alkene.
Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
N
D
N
E
N
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