Organic Chemistry 9th Edition McMurry

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Chapter 06 - An Overview of Organic Reactions
Exhibit 6-1
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. _____

ANSWER: c
POINTS: 1

2. _____

ANSWER: d
POINTS: 1

3. _____

ANSWER: a
POINTS: 1

Exhibit 6-2
Identify the functional groups present in each compound below and predict the direction of polarity in each.

4. mustard gas Cl−CH2CH2−S−CH2CH2−Cl

ANSWER:

POINTS: 1

5.

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Chapter 06 - An Overview of Organic Reactions
ANSWER:

POINTS: 1

Exhibit 6-3
Classify each structure below as a nucleophile or electrophile and briefly explain your choice.

6.
ANSWER: Azide is a nucleophile since it has a net negative charge (and lots of electron pairs!).
POINTS: 1

7.

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

POINTS: 1

8.

ANSWER: Phenol can be a nucleophile or an electrophile

POINTS: 1

Exhibit 6-4
Identify the nucleophile and electrophile in each reaction below and label them.

9.

ANSWER:

POINTS: 1

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Chapter 06 - An Overview of Organic Reactions

10.

ANSWER:

POINTS: 1

11.
ANSWER:

POINTS: 1

Exhibit 6-5
Add curved arrows to the following reactions to indicate the flow of electrons in each.

12.

ANSWER:

POINTS: 1

13.

ANSWER:

POINTS: 1

14.

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Chapter 06 - An Overview of Organic Reactions
ANSWER:

POINTS: 1

15. Acidic ether cleavages are typical substitution reactions. Use the information in Table 6.3 of the textbook to calculate
ΔH° for the reaction of ethyl methyl ether with hydrogen chloride and hydrogen iodide.

a.
b.

Which acid would you predict to be most effective at ether cleavage?

ANSWER: CH3CH2OH +
CH 3CH2OCH3 +
a.
HCl CH3Cl
Bonds broken Bonds formed
436
CH3CH2O−CH3 339 kJ/mol CH3CH2O−H kJ/mol
351
H−Cl 432 kJ/mol CH3−Cl kJ/mol
787
771 kJ/mol
kJ/mol
= ΔH° bonds broken −ΔH°
ΔH° bonds formed = 771 −
787 kJ/mol
= −16 kJ/mol

CH3CH2OH +
b. CH3CH2OCH3C +
HI CH3I
Bonds broken Bonds formed
436
CH3CH2O−CH3 339 kJ/mol CH3CH2O−H kJ/mol
234
H−I 298 kJ/mol CH3−I kJ/mol
670
637 kJ/mol
kJ/mol

= ΔH° bonds broken −ΔH°

ΔH° bonds formed = 637 − 670
kJ/mol
= −33 kJ/mol

Since cleavage with HI is the most

exothermic we would predict that HI would
be most effective at ether cleavage.
POINTS: 1

Exhibit 6-6
MATCH each definition to one of the terms below. Place the letter of the term in the blank to the left of the definition.
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Chapter 06 - An Overview of Organic Reactions

a. polarization f. substitution
b. addition reaction g. nucleophile
c. homolytic bond breakage h. radical reaction
d. electrophile i. elimination reaction
e. polar reaction j. heterolytic bond breakage
16. _____ A process involving symmetrical bond breaking and bond making.
ANSWER: h
POINTS: 1

17. _____ This occurs when both bonding electrons remain with one product fragment.
ANSWER: j
POINTS: 1

18. _____ A reaction where two reactants exchange parts to give two new products.
ANSWER: f
POINTS: 1

19. _____ 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.
ANSWER: g
POINTS: 1

Exhibit 6-7
Consider this reaction when answering the following question(s):

20. Refer to Exhibit 6-7. This reaction is an example of:

a. a substitution reaction.
b. a rearrangement reaction.
c. an addition reaction.
d. an elimination reaction.
ANSWER: b
POINTS: 1

21. Refer to Exhibit 6-7.

The structures below show the step-wise bond making and bond breaking in this reaction.
a.
Draw curved arrows to show the electron flow that has occurred in each step.

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Chapter 06 - An Overview of Organic Reactions

b. Calculate Keq for the reaction in part a.

c. Calculate ΔG° for the reaction in part a.

ANSWER:

a.

b. Keq = [products]/[reactants] = 76/24 = 3.17

c. ΔG°= –RT ln Keq = – 8.314 J/(K • mol)(298) ln 3.17 = –2.86 x 103 J/mol = –2.86 kJ/mol
POINTS: 1

22. The original question has been combined with #21 as part b. This placeholder question is here to maintain the integrity
of the numbering system between the printed copy and ExamView. Therefore, it has been marked "do not use on test" in
ExamView's question information dialog. As a result, this placeholder question is automatically prevented from being
chosen as a test question.
ANSWER: Answer not provided.
POINTS: 1

23. Refer to Exhibit 6-7. Draw a qualitative energy diagram for the reaction (assume that the first step is slower than the
second step). Label fully.
ANSWER:

POINTS: 1

Exhibit 6-8
MATCH each definition to one of the terms below. Place the letter corresponding to the term in the blank to the left of the
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Chapter 06 - An Overview of Organic Reactions
definition.
a. transition state d. standard Gibbs free energy change
b. endergonic reaction e. exergonic reaction
c. activation energy f. reaction intermediate
24. _____ A species that lies at an energy minimum between steps on a reaction.
ANSWER: f
POINTS: 1

25. _____ The energy needed by reactants to reach the transition state.
ANSWER: c
POINTS: 1

26. _____ A reaction where ΔG° is negative.

ANSWER: e
POINTS: 1

27. _____ ΔG° = −RT ln Keq

ANSWER: d
POINTS: 1

Exhibit 6-9
Use the reaction energy diagram below to answer the following question(s).

28. Refer to Exhibit 6-9. 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
ANSWER: b
POINTS: 1

29. Refer to Exhibit 6-9. The transition state is found at point _____ on the diagram.
ANSWER: B
POINTS: 1

30. Refer to Exhibit 6-9. The products are found at point _____ on the diagram.
ANSWER: D
POINTS: 1
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Chapter 06 - An Overview of Organic Reactions
31. Refer to Exhibit 6-9. The free-energy change for the reaction is indicated at point _____ on the diagram.
ANSWER: C
POINTS: 1

32. Refer to Exhibit 6-9. The reactants are found at point _____ on the diagram.
ANSWER: A
POINTS: 1

Exhibit 6-10
Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following question(s).

Diagram 1: The first step of this reaction is shown below.

Diagram 2: The second and third steps of the reaction are shown below.

33. Refer to Exhibit 6-10. This reaction is an example of:

a. a substitution reaction.
b. a rearrangement reaction.
c. an elimination reaction.
d. an addition reaction.
ANSWER: a
POINTS: 1

34. Refer to Exhibit 6-10. In Diagram 1, Species B is:

a. a carbene
b. a carbanion
c. a carbocation
d. a radical
ANSWER: c
POINTS: 1

35. Refer to Exhibit 6-10. In Diagram 1, add curved arrows to indicate electron flow.

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Chapter 06 - An Overview of Organic Reactions
ANSWER:

POINTS: 1

36. Refer to Exhibit 6-10. In Diagram 2, label the nucleophile, Nu, and the electrophile, E+, in the blanks provided under
the structures.
ANSWER:

POINTS: 1

37. Refer to Exhibit 6-10. In Diagram 2, draw arrows on the structures showing electron flow.
ANSWER:

POINTS: 1

38. Refer to Exhibit 6-10. The reaction in Diagram 2 is an example of:

a. a pericyclic reaction.
b. a radical reaction.
c. a concerted reaction.
d. a stepwise reaction.
ANSWER: d
POINTS: 1

39. Refer to Exhibit 6-10. Using the bond dissociations values in the table below, calculate the ΔH° for the reaction in
Diagram 2. Show your calculations for full credit.
Bond D (kJ/mol)
(CH3)3C−Br 263
(CH3)3C−OH 380
HO−H 498
H−Br 366
ANSWER: ΔH° = ΔH° bonds broken − ΔH° bonds formed
= 761 kJ/mol − 746 kJ/mol
= +15 kJ/mol
Bonds Broken Bonds Formed
(CH3)3C−Br 263 kJ/mol (CH3)3C−OH 380 kJ/mol
HO−H 498 kJ/mol H−Br 366 kJ/mol
761 kJ/mol 746 kJ/mol
POINTS: 1

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Chapter 06 - An Overview of Organic Reactions
40. Refer to Exhibit 6-10. Based on all of the data presented in Exhibit 6-10, 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.
ANSWER:

POINTS: 1

Exhibit 6-11
In each reaction below:
a. Label the nucleophile (Nu) and the electrophile (E).
b. Draw arrows on the structures showing electron flow in the reaction.

41.

ANSWER:

POINTS: 1

42.

ANSWER:

POINTS: 1

43. The following represents the carbocation intermediate in the reaction of an alkene with HBr.

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Chapter 06 - An Overview of Organic Reactions

Draw the skeletal structure of the possible products and reactants.

ANSWER: Two possible reactants:

One product:

POINTS: 1

44. What are the major differences between a reaction occurring in flask in the laboratory compared to a reaction
occurring in a biological system?
ANSWER: Solvent: Laboratory reactions occur in nonpolar solvents whereas biological reactions occur in an aqueous
environment.
Temperature: Laboratory reactions can be carried out at very low temperatures or very high temperatures or
anywhere in between whereas biological reactions are limited to the organism’s body temperature which for
warm-blooded species is a very narrow range.
Catalysis: Laboratory reactions can occur with or without catalysts and the catalysts can be acids, bases, metal
surfaces, etc. Biological reactions are catalyzed by large protein molecules called enzymes, that often require
coenzymes or cofactors to function. Laboratory catalysts in general are nonspecific, an acid or Pt surface can
catalyze many different reactants or reactions. Enzymes are highly specific - a given enzyme may only be able
to catalyze the reaction of one reactant (substrate) or one class of reactions.
pH: Laboratory reactions can occur at a variety of pHs whereas biological reactions must function within
narrow physiological pH limits.
POINTS: 1

45. The alkane formed by hydrogenation of (S)-4-methyl-1-hexene is optically active while the one formed by
hydrogenation of (S)-3-methyl-1-pentene is not. Explain.
ANSWER: Each starting alkene is optically active because it contains a chiral center⎯a carbon with four different groups
bonded to it. The alkane formed by the hydrogenation of (S)-4-methyl-1-hexene is optically because carbon
four is still chiral. The product of hydrogenation of (S)-3-methyl-1-pentene is not optically active because two
of the groups on carbon three are the same now⎯they are ethyl groups.
POINTS: 1

46. The enzyme aconitase catalyzes the hydration of the alkene functional group of aconitic acid to give two products,
citric acid and isocitric acid. Isocitric acid is optically active; citric acid is not optically active. Based on your knowledge
of alkene hydration and optical activity, the structure of citric acid is:

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Chapter 06 - An Overview of Organic Reactions

a. b.

c. d. cannot be determined

ANSWER: b
POINTS: 1

47. Which of the following could act as an electrophile?

a. CN– b. NH2–
c. NH3 d. H3O+
ANSWER: d
POINTS: 1

48. Which of the following could act as a nucleophile?

a. HCl b. CH3NH2
c. BF3 d. CH3Br
ANSWER: b
POINTS: 1

49. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.

Which atom is the most electron poor?

a. 1 b. 2
c. 3 d. 4
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Chapter 06 - An Overview of Organic Reactions
ANSWER: b
POINTS: 1

50. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.

Which atom is the most likely to be attacked by a nucleophile?

a. 1 b. 2
c. 3 d. 4
ANSWER: b
POINTS: 1

51. In a polar reaction mechanism, the atom that gives away electrons in a neutral nucleophile will end up as a(n):
a. cation b. anion
c. radical d. neutral molecule
ANSWER: a
POINTS: 1

52. Consider the following.

This process would result in the formation of:

a. a positive ion and negative ion.
b. two neutral species.
c. two radicals.
d. two negative ions.
e. a positive ion and a neutral species.
f. a negative ion and a neutral species.
ANSWER: c
POINTS: 1

53. Consider the following process.

Which of the following correctly applies?

a. termination step b. unsymmetrical bond formation
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Chapter 06 - An Overview of Organic Reactions
c. polar reaction d. produces a radical
ANSWER: a
POINTS: 1

54. A reaction that establishes equilibrium with almost no reactants present:

a. is exergonic.
b. has a negative ΔG°.
c. has a large Keq.
d. all of the above.
ANSWER: d
POINTS: 1

55. A reaction has ΔH° = –14.7 kJ and ΔS° of 35.7 J/(K • mol), will
a. be exergonic. b. have a positive ΔG°.
c. have a very small Keq. d. will proceed rapidly.
ANSWER: a
POINTS: 1

56. Which of the following compounds would produce a single product when treated with Cl2 in the presence of
ultraviolet radiation?
a. butane
b. 2-methylpropane
c. 2,2,-dimethylpropane
d. All would produce multiple products.
ANSWER: c
POINTS: 1

57. Consider a reaction with the following thermodynamic properties.

ΔH° = 77.7 kJ
ΔS° = –35.7 J/(K • mol)
ΔG°= 88.4 kJ
This reaction:
a. will be spontaneous at low temperatures.
b. has bonds in the products that are weaker than the reactants.
c. may have fewer and more complicated molecules in the product.
d. will proceed very slowly.
ANSWER: c
POINTS: 1

58. Consider the following energy diagram for an enzyme-catalyzed reaction.

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Chapter 06 - An Overview of Organic Reactions

How many transition states are involved?

a. 2 b. 3
c. 4 d. 5
ANSWER: c
POINTS: 1

59. Consider the following energy diagram.

Which step has the least endergonic ΔG±?

a. A - C b. C - E
c. E - G d. G - I
ANSWER: a
POINTS: 1

60. Consider the following energy diagram for an enzyme-catalyzed reaction.

Which step is probably the slowest?

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Chapter 06 - An Overview of Organic Reactions
a. A - C b. C - E
c. E - G d. G - I
ANSWER: c
POINTS: 1

61. Consider the following energy diagram for an enzyme-catalyzed reaction.

Which step has the least energetic transition state?

a. A - C b. C - E
c. E - G d. G - I
ANSWER: d
POINTS: 1

62. Write the mechanism of the reaction of trans-2-butene with hydrogen bromide.
ANSWER:

POINTS: 1

63. Write the mechanism of the reaction between water and ammonia.
ANSWER:

POINTS: 1

64. Write the mechanism of the reaction between hydroxide ion and methyl chloride.

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Chapter 06 - An Overview of Organic Reactions
ANSWER:

POINTS: 1

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