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1 Construct an energy profile for the reaction X 6 Y based on the information below. Mark all transition states
and intermediates. State whether each transition state resembles the starting material or the product
for that stage. If you have downloaded the exam, you can use the axes below and the marked starting
material (X) for your figure. Otherwise draw the figure on paper. You do not need to use a ruler. (8 marks)

Information (a) The overall reaction is exergonic.

(b) The reaction occurs in 4 stages.
(c) Stages 1 and 2 are endergonic. Stages 3 and 4 are exergonic. (d) The rate-
determining step is Stage 1.
2 Consider the hypothetical reaction below, together with the experimental data and answer the following (2

marks each)

Experimental data. The rate of reaction increases 4 times when the concentration of X is
doubled. The rate of reaction increases 8 times when the concentration of Y is doubled.
(a) What is the order of the reaction (for example fourth order) with respect to Y?
(b) What is the order of reaction with respect to X?
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(c) How much will the overall rate increase if the concentrations of X and Y are both tripled?
(d) Would you expect solutions of 10g of X and 5g of Y in 50 mL of solvent and 20g of X and 10g of Y in
100 mL of solution to have the same rate?
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3 Calculate the enthalpy of reaction for the following reaction using the supplied bond dissociation enthalpies. (5
marks)
Would you expect that the energy of reaction would be very similar to the enthalpy change? (1 mark)

HC/C!H + F2----> HC/C!F + HF

Bond dissociation enthalpies:
H!F 6 H• + F• ÄHE = 570 kJ/mol HC/C!H 6 HC/C• + H• ÄHE = 547
kJ/mol
F!F 6 F• + F• ÄHE = 159 kJ/mol HC/C!F 6 HC/C• + F• ÄHE = 139
kJ/mol
4 Place the following compounds in order of increasing acidity (least acidic 6 most acidic) (5 marks)

5 Consider the reaction below and complete each sentence by circling or choosing the appropriate underlined
words (1 mark each)
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(a) The benzene in stage 1 is a Brønsted acid Brønsted base Lewis acid Lewis base

(b) The methyl carbocation in stage 1 is a Brønsted acid Brønsted base Lewis acid Lewis base

(c) The arenium ion in stage 2 is a Brønsted acid Brønsted base Lewis acid Lewis base

(d) The chloride ion in stage 2 is a Brønsted acid Brønsted base Lewis acid Lewis base

(e) Stage 1 is a Lewis acid/base Brønsted acid/base reaction.

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6 The pKa of HBr is ~ !9. Select the weakest base from those shown below that will deprotonate the molecule
efficiently. You do NOT need to draw the reaction. (4 marks)

H2O NaOC2H5 CH4 NaNH2

7 Consider the structures below and answer the following questions (Parts a to c 2 marks each; part d 4 marks)

(a) Which structure or structures is a trans compound?

(b) Which structure or structures has the methyl group equatorial?

(c) Which structure or structures has the isopropyl group axial?

(d) Place the 4 groups in order of increasing stability (least stable 6 most stable).
8 Draw curved arrows for each step of the reaction scheme below. (10 marks)
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9 Place the conformations of cis-1-fluoro-4-methylcyclohexane that are drawn below in order of increasing stability
(least stable to most stable). Fluorine is small. (5 marks)

10 Examine each pair of structures below and state whether they are the same, or a pair of stereoisomers. (2 marks each
part)

11 Identify each structure that has a chirality center? (2 marks each structure)
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12 Give two general ways to drive a reaction that is incomplete at equilibrium to completion. (5 marks)
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13 Draw the most stable and least stable Newman projection conformation for the structure that is shown in the Newman
projection shown below. Label which conformation is which. (4 marks) Calculate the strain energies for each of the 2
conformations you drew using the appropriate data in from the table below. All interactions that have zero strain
energy are omitted. (1 mark each calculation)
Note that you can use the terms ‘Et’ for ethyl and ‘Me’ for methyl if you wish.
Note also, you may not need to use all the data from the table.
Eclipsing Interaction Strain Energy kJ/mol Gauche Interaction Strain Energy kJ/mol

H!H 4 CH3!CH3 3.8

CH3!H 5.9 CH3!CH2CH3 4.5
CH3CH2!H 6.4 CH3CH2!CH2CH3 5.0

CH3!CH3 10.5

CH3!CH2CH3 11.0

CH3CH2!CH2CH3 12.0
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14 Give the systematic name for the structure below. (5 marks)

15 Draw the bond-line (or line-angle) structure of 5,5-dichloro-4,4-dimethyl-2,9-decadiynal. (5 marks) 16 Identify the
error in the supplied systematic name for each of the structures below. (2 marks each part)

(a) The error in the name 1-bromo-4-butanol is:

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(b) The error in the name 3,3,3-bromo-1-propanol is:

(c) The error in the name 5-bromo-2-pentanoic acid is:

(d) The error in the name 4-hexenal is: