Klein,: Organic Chemistry
Klein,: Organic Chemistry
Klein,: Organic Chemistry
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Cl
a. (3S,4S)-3-bromo-4-chlorohexane
b. (3S,4S)-3,4-dibromochloroheptane
c. (3R,4R)-3-chloro-4-bromohexane
d. (3R,4R)-3-bromo-4-chlorohexane
e. (3S,4S)-4-bromo-3-chlorohexane
Br Br
Br
Section 7.2
Br Br
Br
a. 1, 2, 3
b. 2, 2, 1
c. 2, 2, 3
d. 3, 2, 2
e. 3, 2, 1
A.
NaCN
Cl CN + NaCl
NC
B. CN
NaCN
Cl CN + NaCl
CN
Cl
C.
CN
NaCN
Cl CN + NaCl
Klein, Organic Chemistry 1e
Answer: c
A. Br NaCN CN
+ NaBr
NC
B.
Br NaCN CN
+ NaBr
NC
Br
CN
C.
Br NaCN CN
+ NaBr
NC
Klein, Organic Chemistry 1e
Answer: a
See p. 290.
a) doubles, doubles
b) halves, halves
c) doubles, halves
d) halves, doubles
e) doubles, will not be effected
f) will not be effected, doubles
a) inversion
b) retention
c) racemization
See p. 291.
Br NaCl, Acetone
NaBr + ??????
A. D.
B. Br E. Cl
C.
a) Primary
b) Secondary
c) Tertiary
10. Identify the correct transition state for this SN2 reaction.
NaCl
I Cl
A. Cl B. Cl
bond making bond making
Cl Cl
bond breaking bond breaking
C. D.
bond making bond making
I I
See p. 297.
a) doubles, doubles
b) halves, halves
c) doubles, halves
d) halves, doubles
e) doubles, will not be effected
f) will not be effected, doubles
Section: 7.5
a) halves, halves
b) doubles, halves
c) halves, doubles
d) doubles, will not be effected
e) will not be effected, doubles
See p. 299.
a) tetrahedral
b) octahedral
c) bent
d) linear
e) trigonal pyramidal
f) trigonal planar
See p. 299.
Section: 7.5
a) tetrahedral
b) octahedral
c) bent
d) trigonal pyramidal
e) trigonal planar
15. SN1 reactions where there is only one stereocenter and the
leaving group is attached to that stereocenter will produce
________ products.
a) inverted
b) identical
c) racemic
See p. 301-302.
A. Br
B. Br Br
C.
Br Br
D. Br
NaCl, H2O
NaI + H2O + ??????
I
A. D.
B. E.
Cl I
C.
See p. 303.
a) stability, substrate
b) steric hindrance, stability
c) substrate, concentration
d) stability, steric hindrance
a) weak, stable
b) strong, stable
c) weak, unstable
d) strong, unstable
The more stable the anion produced by the leaving group the
more likely the leaving group is to break off the substrate.
That makes it a good leaving group. Weak bases are the
most stable anions. If an anion is unstable it wants to react
and that makes it a strong base.
a) Br-
b) Cl-
c) F-
d) I-
See p. 318-320.
a) A
b) B
c) C
d) D
e) A and D
f) A, B and D
g) all of the above
Section: 7.8
a. A
b. B
c. A and B
d. A, B and D
e. all of the above
a) SN1
b) SN2
c) SN1 solvolysis
a) SN1
b) SN2
c) SN1 solvolysis
a) SN1
b) SN2
c) SN1 solvolysis
a) Primary
b) Secondary
c) Tertiary
I
NaBr, H2O
NaI + ??????
A. D.
I
B. E.
I
C.
Br NaOMe, MeOH
NaBr + ??????
A. D.
B. Br E. OMe
C.
SN2 reaction occurs with primary substrate and any base but
a sterically hindered base such as potassium tert-butoxide.
For more examples of this type of problem, see Skillbuilder
7.8.
1. NaBr/acetone
B. Br SH 2. NaBr/water
3. NaCl/acetone
4. NaCl/water
5. NaCN/acetone A.
6. NaCN/water
C. OH OCH3 7. NaOCH3/acetone B.
8. NaOCH3/water
9. NaSH/acetone C.
10. NaSH/water
Br
11. TsCl, pyridine D.
D. OH
E.
E.
F.
I Cl
F.
I Cl
Klein, Organic Chemistry 1e
Answer: A: 5
B: 10
C. 11, 7
D. 11, 3, 1
E. 3
F. 1, 3
Section: 7.8
30. List the reagents necessary for each transformation below. If more than
one reagent is necessary for a reaction, list them in order (for example, if
you need reagent 8 then reagent 6, you would enter: 8, 6)
A. Br CN
1. NaBr/acetone
B. Br SH 2. NaBr/water
3. NaCl/acetone
4. NaCl/water
5. NaCN/acetone
6. NaCN/water
C. OH OCH3 7. NaOCH3/acetone
8. NaOCH3/water
9. NaSH/acetone
10. NaSH/water
11. TsCl, pyridine
D. OH Br
E. a. A = 5; B = 9; C = 11, 7; D = 11, 3, 1; E = 3; F = 1, 3
b. A = 5; B = 10; C = 11, 8; D = 11, 3, 2; E = 4; F = 2, 4
I Cl
c. A = 5; B = 10; C = 11, 7; D = 11, 1; E = 3; F = 1, 3
F.
d. A = 6; B = 9; C = 11, 7; D = 11, 1; E = 3; F = 1, 3
I Cl
e. A = 6; B = 10; C = 11, 8; D = 11, 2; E = 4; F = 2, 4
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