Professional Documents
Culture Documents
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. _____
2. _____
3. _____
Exhibit 6-2
Identify the functional groups present in each compound below and predict the direction of polarity in each.
5.
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!).
7.
8.
Exhibit 6-4
Identify the nucleophile and electrophile in each reaction below and label them.
9.
10.
11.
Exhibit 6-5
Add curved arrows to the following reactions to indicate the flow of electrons in each.
12.
ANSWER:
POINTS: 1
13.
14.
15. Acidic ether cleavages are typical substitution reactions. Use the information in Table 6.3 of the textbook to calculate
H for the reaction of ethyl methyl ether with hydrogen chloride and hydrogen iodide.
a.
b.
Complete the
Cengage Learning Testing, Powered by Cognero Page 3
Chapter 06 - An Overview of Organic Reactions
analysis to answer
this question
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.
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.
17. _____ This occurs when both bonding electrons remain with one product fragment.
18. _____ A reaction where two reactants exchange parts to give two new products.
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.
Exhibit 6-7
Consider this reaction when answering the following question(s):
a.
c. G= RT ln Keq = 8.314 J/(K mol)(298) ln 3.17 = 2.86 x 103 J/mol = 2.86 kJ/mol
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
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.
25. _____ The energy needed by reactants to reach the transition state.
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
Cengage Learning Testing, Powered by Cognero Page 6
Chapter 06 - An Overview of Organic Reactions
c. a slow endothermic reaction
d. a fast endothermic reaction
29. Refer to Exhibit 6-9. The transition state is found at point _____ on the diagram.
30. Refer to Exhibit 6-9. The products are found at point _____ on the diagram.
31. Refer to Exhibit 6-9. The free-energy change for the reaction is indicated at point _____ on the diagram.
32. Refer to Exhibit 6-9. The reactants are found at point _____ on the diagram.
Exhibit 6-10
Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following question(s).
Diagram 2: The second and third steps of the reaction are shown below.
35. Refer to Exhibit 6-10. In Diagram 1, add curved arrows to indicate electron flow.
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:
37. Refer to Exhibit 6-10. In Diagram 2, draw arrows on the structures showing electron flow.
39. Refer to Exhibit 6-10. Using the bond dissociations values in the table below, calculate the H for the reaction in
Diagram 2. Show your calculations for full credit.
Bond D (kJ/mol)
(CH3)3CBr 263
(CH3)3COH 380
Cengage Learning Testing, Powered by Cognero Page 8
Chapter 06 - An Overview of Organic Reactions
HOH 498
HBr 366
ANSWER: H = H bonds broken H bonds formed
= 761 kJ/mol 746 kJ/mol
= +15 kJ/mol
Bonds Broken Bonds Formed
(CH3)3CBr 263 kJ/mol (CH3)3COH 380 kJ/mol
HOH 498 kJ/mol HBr 366 kJ/mol
761 kJ/mol 746 kJ/mol
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.
42.
ANSWER:
Cengage Learning Testing, Powered by Cognero Page 9
Chapter 06 - An Overview of Organic Reactions
43. The following represents the carbocation intermediate in the reaction of an alkene with HBr.
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 organisms 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.
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. Draw the structures of reactants and structures to understand this
question and the answer below.
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 active because
carbon four is still chiral. The product of hydrogenation of (S)-3-methyl-1-pentene is not optically active
Cengage Learning Testing, Powered by Cognero Page 10
Chapter 06 - An Overview of Organic Reactions
because two of the groups on carbon three are the same now they are ethyl groups.
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:
a. b.
c. d. cannot be determined
49. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.
50. Consider the following grayscale electrostatic potential map. The regions are labeled as to color.
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
POINTS: 1
62. Write the mechanism of the reaction of trans-2-butene with hydrogen bromide.
63. Write the mechanism of the reaction between water and ammonia.
64. Write the mechanism of the reaction between hydroxide ion and methyl chloride.