Example Term Test 2a, 59-230/2; Nov.

6, 2015
Last Name: First Name: ID:
Lab Section or Weekday and Time:
Q1 Q2 Q3 Q4 Q5 Q6 Q7 MC Total

/15 /6 /12 /10 /6 /17 /12 /60 /138

Short Answer Questions (78/138)

1) Name the following molecules according to IUPAC rules. Exclusively use E/Z and R/S nomenclature
for the assignment of configuration of double bonds and chiral centres, respectively. Omit the
assignment of E/Z and R/S configurations in the name if only one of the two stereoisomers can
chemically exist.
(3 marks for each molecule; -0.5 for each mistake)

a.

(2S,5S)-2-chloro-5-methylheptane

b.

(2R,3S,4S,5R)-2-bromo-5-chloro-3,4-dimethylhexane

c.

(R,E)-3-nitrohept-5-en-1-yne (also fine (3R,5E) or (5E,3R)

d.

(4S,5S)-4-tert-butyl-1-isopropyl-5-methylcyclopent-1-ene
(-0.5 if Z included)

e.

(1S,2S,4S)-2-chloro-1-ethyl-4-fluorocyclohexane
(just (S,S,S) is also fine)
2) Draw all enantiomers and diastereomers for the following molecule without rotating the pentane
chain (use the same zig-zag representation of pentane). Label which one is which. (6 marks)

Answers:

3) Which side of the equilibrium is favored for the following reactions?

Explain your choices in not more than 4 sentences for each example. (12 marks)
a)

Answer:
The staring materials are favored because they are not charged and are therefore more stable.

b)

Answer:
The products are favored because a negative charge is more stable on oxygen than on nitrogen. This is
true because oxygen is more electronegative than nitrogen.
4) Draw the mechanism and supply the products for the following proton transfer reaction. Be sure your
mechanism includes all mechanism arrows, lone pairs, and formal charges. Also supply a free energy
diagram. On the diagram, label the axes, the reactants and products, the transition state, ΔG0‡, and
ΔG0rxn. (10 marks)

Answer:

4 marks (-0.5 for each missing lone pair and charge)

0.5 each = 6 marks

5) Rank the following carbocations in order of most stable to least stable (e.g. I > II > III > IV).
(6 marks)

Answer:
III > I > IV > II 2 marks for each correct pair;
1 mark for III first and/or II last if nothing else is correct;

6) Using the two reactants shown below, draw the mechanisms and products for reactions based on four
different mechanisms: SN1, E1, SN2 and E2 (do not include any solvent molecules). (17 marks)

Br + O

Answer:

Arrows 0.5, structures including lone pairs and charges 1 (-0.5 for each structure for missing lone pair or
charge)
SN1 = 4; E1 = 5.5; SN2 = 3; E2 = 4.5 total = 17
7) For the following two sets of reactions, use the table below to identify which mechanism is favored
by each factor, and determine which mechanism is favoured overall. (12 marks)
a)

Δ = heat, here 80 °C; 100 equivalences of the nucleophile/base were added;

Overall favoured is:

b)

The reaction was run at 30 °C with 100 equivalences of the nucleophile/base;

Overall favoured is:

1 mark for each correct row and statement for overall outcome; One mistake per row is still 0.5 marks;
 Twenty Multiple Choice Questions (each 3 points = 60) Last Name:
First Name:
1) Which of the following is achiral?
a. A helical seashell d. A pair of glasses
b. A baseball glove e. A shoe
c. A pair of scissors

2) What is the maximum number of stereoisomers possible for the following molecule?

a. Two d. Six
b. Three e. Eight
c. Four

3) Which of the following has/have exactly two stereocenters?

a. I d. IV
b. II e. I and IV
c. III

4) Which structure (or structures) represents (or represent) the enantiomer of the molecule below?

a. I d. IV
b. II e. III and IV
c. III
5) Which of the following molecules is achiral?

a. I d. IV
b. II e. V
c. III

6) What is the relationship between the two following molecules?

a. They are enantiomers. d. They are unrelated.

b. They are diastereomers. e. They are the same molecule.
c. They are conformational isomers.

7) If (+) ibuprofen has a specific rotation of +57, what is the specific rotation of a racemic mixture of
ibuprofen?
a. 57
b. –57
c. 26.5
d. 0
e. Cannot be determined with the information given

8) What is the correct proton transfer mechanism for the following reaction?

a. I d. IV
b. II e. V
c. III
9) Which of the following compounds is most acidic?

a. I d. IV
b. II e. V
c. III

10) Which of the compounds is most acidic?

a. I d. IV
b. II e. V
c. III

11) Which of the following compounds is most acidic?

a. I d. IV
b. II e. V
c. III

12) Which of the compounds is most basic?

a. I d. IV
b. II e. V
c. III
13) Which of the following resonance structures contributes most to the resonance hybrid?

a. I
b. II
c. III
d. IV
e. I and II equally contribute most to the hybrid

14) Which is true of a free energy diagram for an SN1 reaction?

a. It shows one transition state.
b. It always shows that the reaction is net exothermic.
c. It never shows intermediates.
d. It always shows that the reaction is net endothermic.
e. It always includes multiple energy barriers (transition states).

15) Which of the following steps could be found in an E1 mechanism?

a. I d. IV
b. II e. V
c. III

16) Which of the following could be the rate law for an SN1 reaction?
a. Rate = k[A] d. Rate = k[A][B]2
2
b. Rate = k[A] e. Rate = k[A]2[B]2
c. Rate = k[A][B]

17) What is the rate law for the following SN2 reaction?

a. Rate = k[A] d. Rate = k[B]2

b. Rate = k[B] e. Rate = k[A][B]
c. Rate = k[A]2
18) What is the most likely product of the following SN2 reaction?

a. I d. IV
b. II e. A racemic mixture of II and III
c. III

19) Which of the following proton transfers is most likely to occur in an acidic solution?

a. I
b. II
c. III
d. IV
e. All of these are likely in an acidic solution.

20) Which attacking species would favor an E2 reaction over an SN2 reaction?

a. I d. IV
b. II e. V
c. III