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10

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CHEM 2P20 Test 1 - Solutions
May 14, 2014
Duration: 90 minutes

Total: 72 Marks

This test contains 8 pages and 6 questions. Answer NEATLY in the space provided. It is
YOUR responsibility to ensure that your answers are legible. Illegible answers will be
marked as incorrect. Answers written in pencil WILL NOT be remarked. Molecular
models are permitted. DO NOT remove pages from the test package.

Page 1 of 8

[10] 1. Draw Lewis dot structures for the following species:

(a) N2H4
H
.. H
..
H:N:N:H (2)

(b) N2H2
H:N::N:H (2)

(c) H3CCN
H
..
H:C:C::N
..
H
(2)
(d) H3CHO
H
..
H:C:O:H
..
H
(2)

(e) H2SO4
H
..
O
..
O::S::O
..
O
..
H

(2)

Page 2 of 8

[6] 2. The following compound can be protonated on any of the three nitrogen atoms,
however, one of these nitrogen atoms is more basic than the others. Draw the
conjugate acid resulting from the protonation of the most basic nitrogen atom
and explain why your choice of N1, N2, or N3 represents the most basic
nitrogen atom.
1

H
N

NH

NH 2
3

H
N

NH 2

NH 2

(3)
Protonation of nitrogen 2 gives resonance forms (1) that delocalize the positive charge
over all three nitrogen atoms and a carbon atom (1). This represents a very stable
condition (1). Since nitrogen 2 will be protonated preferentially it is the most basic.
3

Page 3 of 8

[7] 3. Using numbers rank the following species in order of increasing acidity (1 = least
acidic, 7 = most acidic)
NH3

HF

1 (1)

5 (1)

H3CCOOH
4 (1)

H2SO 4

H3COH

7 (1)

3 (1)

H3O+

H2O

6 (1)

2 (1)

Page 4 of 8

[6] 4. Draw two chair conformations of each compound and label the substituents as
axial and equatorial. In each case, indicate which conformation is the most
stable.
(a) cis-1-ethyl-3-methylcyclohexane
(1)

(1)

most stable (1)

(b) trans-1-ethyl-4-methylcyclohexane
(1)

(1)

most stable (1)

Page 5 of 8

[34] 5. In the spaces below each structure provide the IUPAC name. At the bottom of
the group indicate which structures (I, II, VI, etc.) represent the same compound.
(a)

II

III

trans-1,4-dimethyl
cyclohexane (2)

cis-1,4-dimethylcyclohexane (2)

IV

V
H
H

VI
H

cis-1,3-dimethylcyclohexane (2)

cis-1,4-dimethylcyclohexane (2)

trans-1,4-dimethyl
cyclohexane (2)

trans-1,4-dimethyl
cyclohexane (2)

The following structures (I, III, IV, etc.) represent the same compound(s) or a unique
compound:
I & III (2)
II & V & VI (3)
IV (2)

Page 6 of 8

(b)

II

III
H

H
H

2,3-dimethylbutane (2)

2,3-dimethylbutane (2)

IV

2,2-dimethylbutane (2)

V
H

2,3-dimethylbutane (2)

2,2-dimethylbutane (2)

The following structures (I, III, IV, etc.) represent the same compound(s) or a unique
compound:
I & II & IV (3)
III & V (2)

Page 7 of 8

[9] 6. Conformation studies on ethane-1,2-diol (HOCH2CH2OH) have shown the most

stable conformation about the central C-C bond to be the gauche conformation,
which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw
Newman projections of these two conformers and explain this curious result.

H
H

OH

OH

(3)

(3)
H

OH

OH
H

Hydrogen bonding! (1) Moving the two OH groups closer together permits the H of one
alcohol to come closer to the O of the other alcohol (1). Such intramolecular hydrogen
bonding cannot take place in the anti conformation where the two OH groups are too far
apart (1).

Page 8 of 8