Chapter 5 Practice

Problems

Reaction 5-1
Classify each reaction below as a(n):

a. addition
b. elimination
c. substitution
d. rearrangement

Place the letter corresponding to the correct answer in the blank to the left of the reaction.

1. Refer to Reaction 5-1. __________

2. Refer to Reaction 5-1. __________

3. Refer to Reaction 5-1. __________

4. Identify the functional groups present in each compound and predict the direction of polarity in each.

mustard gas Cl−CH2CH2−S−CH2CH2−Cl

5. Identify the functional groups present in each compound and predict the direction of polarity in each.

6. Classify each structure below as a nucleophile or electrophile and briefly explain your choice.
 7. Classify each structure below as a nucleophile or electrophile and briefly explain your choice.

8. Classify each structure below as a nucleophile or electrophile and briefly explain your choice.

9. Identify the nuclephile and electrophile in the reaction below and label them.

10. Identify the nuclephile and electrophile in the reaction below and label them.

11. Identify the nuclephile and electrophile in the reaction below and label them.

12. Add curved arrows to the following reaction to indicate the flow of electrons in each.

13. Add curved arrows to the following reaction to indicate the flow of electrons in each.

Matching 5-1
MATCH each definition to one of the terms below. Place the letter of the term in the blank to the left of the
definition.
 a. polarization
b. addition reaction
c. homolytic bond breakage
d. electrophile
e. polar reaction
f. substitution
g. nucleophile
h. radical reaction
i. elimination reaction
j. heterolytic bond breakage

14. Refer to Matching. __________ A process involving symmetrical bond breaking and bond making.
15. Refer to Matching 5-1. __________ This occurs when both bonding electrons remain with one product
fragment.
16. Refer to Matching 5-1. __________ A reaction where two reactants exchange parts to give two new products.
17. Refer to Matching 5-1. __________ A general term for species which have electron rich sites that can form a
bond by donating a pair of electrons to an electron poor site.

Reaction 5-2
Consider this reaction when answering the following questions:

18. Refer to Reaction 5-2. Draw a qualitative energy diagram for the reaction (assume that the first step is slower
than the second step). Label fully.

Matching 5-2
MATCH each definition to one of the terms below. Place the letter corresponding to the term in the blank to
the left of the definition.

a. transition state
b. endergonic reaction
c. activation energy
d. standard Gibbs free energy change
e. exergonic reaction
f. reaction intermediate

19. Refer to Matching 5-2. __________ A species that lies at an energy minimum between steps on a reaction.
20. Refer to Matching 5-2. __________ The energy needed by reactants to reach the transition state.
21. Refer to Matching 5-2. __________ A reaction where ΔG° is negative.
22. Refer to Matching 5-2. __________ ΔG° = −RT1n Keq.

Reaction 5-3
Use the reaction energy diagram below to answer the following questions.

23. Refer to Reaction 5-3. The reaction depicted in this reaction energy diagram can best be described as:

a. a slow exothermic reaction

b. a fast exothermic reaction
c. a slow endothermic reaction
d. a fast endothermic reaction
24. Refer to Reaction 5-3. The transition state is found at point __________ on the diagram.
25. Refer to Reaction 5-3. The products are found at point __________ on the diagram.
26. Refer to Reaction 5-3. The free-energy change for the reaction is indicated at point __________ on the
diagram.
27. Refer to Reaction 5-3. The reactants are found at point __________ on the diagram.

2-bromo-2-bethylpropane

The First Step of the Reaction:

The Second and Third Steps of the Reaction:

28. Refer to 2-bromo-2-bethylpropane. Consider the reaction of 2-bromo-2-methylpropane with water. This
reaction is an example of:

a. a substitution reaction.
b. a rearrangement reaction.
c. an elimination reaction.
d. an addition reaction.
29. Refer to 2-bromo-2-methylpropane. Species B (First Step) is:

a. a carbene
b. a carbanion
c. a carbocation
d. a radical
30. Refer to 2-bromo-2-methylpropane. Add curved arrows to indicate electron flow in the first step.
31. Refer to 2-bromo-2-methylpropane. Label the nucleophile, Nu, and the electrophile, E+, in the blanks
provided under the structures (Second and Third Steps).
32. Refer to 2-bromo-2-methylpropane. Draw arrows on the structures above showing electron flow in steps two
and three of this reaction.
33. Refer to 2-bromo-2-methylpropane. This reaction (Second and Third Steps) is an example of:

a. a pericyclic reaction.
b. a radical reaction.
c. a concerted reaction.
d. a polar reaction.
34. Refer to 2-bromo-2-methylpropane. Using the bond dissociations values in the table below, calculate the ΔH°
for this reaction. Show your calculations for full credit.

35. Refer to 2-bromo-2-methylpropane. Draw a qualitative reaction energy diagram for the reaction of
2-bromo-2-methylpropane with water. The first step is the slowest step of the reaction. Fully label the
diagram, including the coordinates.
36. In each reaction:
 a) Label the nucleophile (Nu) and the electrophile (E).
b) Draw arrows on the structures showing electron flow in the reaction

37. In each reaction:

a) Label the nucleophile (Nu) and the electrophile (E).

b) Draw arrows on the structures showing electron flow in the reaction
Chapter 5 Practice
Answer Section

PROBLEM

1. ANS:
c

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2. ANS:
d

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3. ANS:
a

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4. ANS:

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5. ANS:

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6. ANS:
Azide is a nucleophile since it has a net negative charge (and lots of electron pairs!).

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7. ANS:
Hydronium ion is an electrophile since it has a positive charge.

PTS: 1
8. ANS:
Phenol can be a nucleophile or an electrophile
 PTS: 1
9. ANS:

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10. ANS:

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11. ANS:

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12. ANS:

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13. ANS:

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14. ANS:
 h

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15. ANS:
j

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16. ANS:
f

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17. ANS:
g

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18. ANS:

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19. ANS:
f

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20. ANS:
c

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21. ANS:
e

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22. ANS:
d

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23. ANS:
b

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24. ANS:
B.

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25. ANS:
D.

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26. ANS:
C.

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27. ANS:
A.

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28. ANS:
a.

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29. ANS:
c

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30. ANS:

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31. ANS:

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32. ANS:
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33. ANS:
d

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34. ANS:

ΔH° = ΔH° bonds broken - ΔH° bonds formed

= 761 kJ/mol - 746 kJ/mol
= +15 kJ/mol

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35. ANS:

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36. ANS:

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37. ANS:
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