Klein,: Organic Chemistry

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Chapter 7

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Klein, Organic Chemistry 1e


Section: 7.2

1. What is the correct IUPAC name for the following


structure? Br

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

Klein, Organic Chemistry 1e


Answer: a

Klein, Organic Chemistry 1e


 Section 7.2

2. Going from left to right, classify each halide as 1o, 2o or 3o (use


1, 2 and 3 on the number pad for 1o, 2o and 3o)

Br Br

Br

Klein, Organic Chemistry 1e


Answer : 3, 2, 1

Identify the carbon where the functional group is attached


as either a CH2, CH or C. If the carbon is a CH2, the
functional group is primary. If the carbon is a CH, the
functional group is secondary. If the carbon is a C, the
functional group is tertiary. In this molecule, the Bromine is
attached to a C. This makes the bromine a tertiary halide.

Klein, Organic Chemistry 1e


Alternate Answers:

 Section 7.2

2. Going from left to right, classify each halide as 1o, 2o or 3o (use


1, 2 and 3 on the number pad for 1o, 2o and 3o)

Br Br

Br

a. 1, 2, 3
b. 2, 2, 1
c. 2, 2, 3
d. 3, 2, 2
e. 3, 2, 1

Klein, Organic Chemistry 1e


Answer : e

Klein, Organic Chemistry 1e


Section: 7.3

3. Assuming the reaction below takes place by a concerted


process, which mechanistic scheme is correct?
NaCN
Cl CN + NaCl

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

For more examples of this type of problem, see


Skillbuilder 7.1 and 7.7.

Klein, Organic Chemistry 1e


Section: 7.3

4. Assuming the reaction below takes place by a stepwise


process, which mechanistic scheme is correct?
Br NaCN CN
+ NaBr

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

For more examples of this type of problem, see Skillbuilder 7.1


and 7.6.

Klein, Organic Chemistry 1e


Section: 7.4

5. SN2 reactions are ________ and have ________ kinetics.

a) unimolecular, 2nd order


b) unimolecular, 1st order
c) bimolecular, 2nd order
d) bimolecular, 1st order

Klein, Organic Chemistry 1e


Answer: c

See p. 290.

Klein, Organic Chemistry 1e


Section: 7.4

6. In an SN2 reaction, if the [nucleophile] doubles, the reaction rate


________. In an SN2 reaction, if the [substrate] doubles, the
reaction rate ________.

a) doubles, doubles
b) halves, halves
c) doubles, halves
d) halves, doubles
e) doubles, will not be effected
f) will not be effected, doubles

Klein, Organic Chemistry 1e


Answer: a

In an SN2 reaction, the reaction rate is affected by both the


nucleophile and the substrate. That is what bimolecular means in
this case.

Klein, Organic Chemistry 1e


Section: 7.4

7. SN2 reactions where there is only one stereocenter and the


leaving group is attached to that stereocenter will produce
________ products.

a) inversion
b) retention
c) racemization

Klein, Organic Chemistry 1e


Answer: a

See p. 291.

Klein, Organic Chemistry 1e


Section: 7.4

8. What is the major product of the following reaction?

Br NaCl, Acetone
NaBr + ??????

A. D.

B. Br E. Cl

C.

Klein, Organic Chemistry 1e


Answer: e

SN2 reaction occurs with primary substrate and polar aprotic


solvent. For more examples of this type of problem, see
Skillbuilder 7.2.

Klein, Organic Chemistry 1e


Section: 7.4

9. SN2 reactions proceed fastest with ________ substrates.

a) Primary
b) Secondary
c) Tertiary

Klein, Organic Chemistry 1e


Answer: a

Primary substrates have the least steric hindrance


and their reaction rates are the fastest.

Klein, Organic Chemistry 1e


Section: 7.4

10. Identify the correct transition state for this SN2 reaction.

NaCl

I Cl

 
A. Cl B. Cl
bond making bond making

bond breaking bond breaking


I I
 

 
Cl Cl
bond breaking bond breaking
C. D.
bond making bond making
I I
 

Klein, Organic Chemistry 1e


Answer: b

SN2 reaction transition states show a bond making between the


nucleophile and the carbon while the leaving group bond is
starting to break. Both the incoming nucleophile and the leaving
group have partial negative charges. For more examples of this
type of problem, see Skillbuilder 7.3.

Klein, Organic Chemistry 1e


Section: 7.5

11. SN1 reactions are ________ and have ________ kinetics.

a) unimolecular, 2nd order


b) unimolecular, 1st order
c) bimolecular, 2nd order
d) bimolecular, 1st order

Klein, Organic Chemistry 1e


Answer: b

See p. 297.

Klein, Organic Chemistry 1e


Section: 7.5

12. In an SN1 reaction, if the [nucleophile] doubles, the reaction


rate ________. In an SN1 reaction, if the [substrate] doubles, the
reaction rate ________.

a) doubles, doubles
b) halves, halves
c) doubles, halves
d) halves, doubles
e) doubles, will not be effected
f) will not be effected, doubles

Klein, Organic Chemistry 1e


Answer: f

In an SN1 reaction, the reaction rate is affected by only the


substrate. That is what unimolecular means in this case.

Klein, Organic Chemistry 1e


Alternate Answer:

Section: 7.5

12. In an SN1 reaction, if the [nucleophile] doubles, the reaction


rate ________. In an SN1 reaction, if the [substrate] doubles, the
reaction rate ________.

a) halves, halves
b) doubles, halves
c) halves, doubles
d) doubles, will not be effected
e) will not be effected, doubles

Klein, Organic Chemistry 1e


Answer: e

Klein, Organic Chemistry 1e


Section: 7.5

13. The general order for stability of carbocations is __________.

a) methyl > tertiary > secondary > primary


b) methyl > primary > secondary > tertiary
c) tertiary > secondary > primary > methyl
d) secondary > tertiary > primary > methyl

Klein, Organic Chemistry 1e


Answer: c

See p. 299.

Klein, Organic Chemistry 1e


Section: 7.5

14. Carbocations have __________ geometry.

a) tetrahedral
b) octahedral
c) bent
d) linear
e) trigonal pyramidal
f) trigonal planar

Klein, Organic Chemistry 1e


Answer : f

See p. 299.

Klein, Organic Chemistry 1e


Alternate Answers:

Section: 7.5

14. Carbocations have __________ geometry.

a) tetrahedral
b) octahedral
c) bent
d) trigonal pyramidal
e) trigonal planar

Klein, Organic Chemistry 1e


Answer : e

Klein, Organic Chemistry 1e


Section: 7.5

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

Klein, Organic Chemistry 1e


Answer : c

See p. 301-302.

Klein, Organic Chemistry 1e


Section: 7.5

16. What would be the correct pathway to form the carbocation


intermediate for the following reactions?
Br Cl
NaCl/H2O

A. Br

B. Br Br

C.
Br Br

D. Br

Klein, Organic Chemistry 1e


Answer: a

For more examples of this type of problem, see Skillbuilder 7.4.

Klein, Organic Chemistry 1e


Section: 7.5

17. What is the major product of the following reaction?

NaCl, H2O
NaI + H2O + ??????
I

A. D.

B. E.
Cl I

C.

Klein, Organic Chemistry 1e


Answer: b

SN1 reaction occurs with tertiary substrate. For more examples


of this type of problem, see Skillbuilder 7.5.

Klein, Organic Chemistry 1e


Section: 7.4, 7.5 and 7.8

18. The SN2 mechanism is characterized by the presence of a


single ________. The SN1 mechanism is characterized by the
formation of a(n) _________ called a(n) ________.

a) intermediate, transition state, carbocation


b) transition state, intermediate, carbanion
c) intermediate, intermediate, carbanion
d) transition state, intermediate, carbocation
e) transition state, transition state, carbocation

Klein, Organic Chemistry 1e


Answer: d

See p. 303.

Klein, Organic Chemistry 1e


Section: 7.4, 7.5 and 7.8

19. In an SN2 reaction, reaction rates are affected by the


__________ of the substrate. In an SN1 reaction, reaction rates
are determined by the __________ of the carbocation.

a) stability, substrate
b) steric hindrance, stability
c) substrate, concentration
d) stability, steric hindrance

Klein, Organic Chemistry 1e


Answer: b

In an SN2 reaction, the reaction rate is affected by how bulky and


hindered the substrate is for back-side attack. In an SN1 reaction,
the reaction rate is most affected by the stability of a carbocation.

Klein, Organic Chemistry 1e


Section: 7.8

20. The best leaving group produces a _________ base that is


a(n) _________ anion.

a) weak, stable
b) strong, stable
c) weak, unstable
d) strong, unstable

Klein, Organic Chemistry 1e


Answer is: a

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.

Klein, Organic Chemistry 1e


Section: 7.8

21. Which is the best leaving group?

a) Br-
b) Cl-
c) F-
d) I-

Klein, Organic Chemistry 1e


Answer: d

On the periodic chart, basicity increases as you go up the chart in


a group or as you go left across a period. Iodine is the lowest in
the 17th group and therefore is the weakest base. Recall, weakest
base = best leaving group.

Klein, Organic Chemistry 1e


Section: 7.8

22.SN1 reactions run best in __________ solvents and SN2


reactions run best in _________ solvents.

a) polar protic, polar protic


b) polar protic, polar aprotic
c) polar aprotic, polar aprotic
d) polar aprotic, polar protic

Klein, Organic Chemistry 1e


Answer: b

See p. 318-320.

Klein, Organic Chemistry 1e


Section: 7.8

23. Which of the following is a polar protic solvent?

a) A
b) B
c) C
d) D
e) A and D
f) A, B and D
g) all of the above

Klein, Organic Chemistry 1e


Answer: f

Polar protic solvents have an OH or NH in their structure.

Klein, Organic Chemistry 1e


Alternate Answers:

Section: 7.8

23. Which of the following is a polar protic solvent?

a. A
b. B
c. A and B
d. A, B and D
e. all of the above

Klein, Organic Chemistry 1e


Answer: d

Klein, Organic Chemistry 1e


Section: 7.4, 7.5, 7.6, 7.7 and 7.8

24. Which mechanism(s) is represented by the following?

a) SN1
b) SN2
c) SN1 solvolysis

Klein, Organic Chemistry 1e


Answer: b

SN2 mechanisms are characterized by having just a transition


state (only 1 “energy hill” in the energy diagram).

Klein, Organic Chemistry 1e


Section: 7.4, 7.5, 7.6, 7.7 and 7.8

25. Which mechanism(s) is represented by the following?

a) SN1
b) SN2
c) SN1 solvolysis

Klein, Organic Chemistry 1e


Answer: a

SN1 mechanisms are characterized by the formation of a


carbocation intermediate (2 “energy hills” in the energy
diagram).

Klein, Organic Chemistry 1e


Section: 7.4, 7.5, 7.6, 7.7 and 7.8

26. Which mechanism(s) is represented by the following?

a) SN1
b) SN2
c) SN1 solvolysis

Klein, Organic Chemistry 1e


Answer: c

SN1 solvolysis mechanisms are characterized by the


formation of a carbocation and by the removal of a hydrogen
to form the final product (3 “energy hills” in the energy
diagram).

Klein, Organic Chemistry 1e


Section: 7.8

27. SN2 reactions generally proceed fastest with ________


substrates.

a) Primary
b) Secondary
c) Tertiary

Klein, Organic Chemistry 1e


Answer: a

Primary substrates have the least steric hindrance and their


reaction rates are the fastest.

Klein, Organic Chemistry 1e


Section: 7.8

28. What is the major product of the following reaction?

I
NaBr, H2O
NaI + ??????

A. D.

I
B. E.

I
C.

Klein, Organic Chemistry 1e


Answer: d

SN1 reaction occurs with secondary substrate and polar


protic solvent. For more examples of this type of problem,
see Skillbuilder 7.8.

Klein, Organic Chemistry 1e


Section: 7.8

29.What is the major product of the following reaction?

Br NaOMe, MeOH
NaBr + ??????

A. D.

B. Br E. OMe

C.

Klein, Organic Chemistry 1e


Answer: e

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.

Klein, Organic Chemistry 1e


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 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

For more examples of this type of problem, see Skillbuilder


7.9.

Klein, Organic Chemistry 1e


Alternate Answers:

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

Klein, Organic Chemistry 1e


Answer: a

Klein, Organic Chemistry 1e

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