CHM 138H

INTRODUCTORY ORGANIC CHEMISTRY I

TERM TEST I
October 21st 2015
TOTAL MARKS: 70

FAMILY NAME, FIRST NAME (PRINT): _________________________________________

Student #: ________________________
TUTORIAL GROUP #:

T________

Answer all questions in the spaces provided on the accompanying answer sheet.
It is attached to the back of the test paper. You may detach the answer sheet.
Nothing written on this question sheet will be graded. All answers must be
written on the answer sheet within the time allowed.

PRINT YOUR NAME, STUDENT NUMBER, and TUTORIAL GROUP

NUMBER on this test paper and on the answer sheet. Write all answers in
blue or black ink.

You may use unboxed molecular models. Calculators are not permitted.

A periodic table and some useful physical values are included on page 4 of the
test.

At the end of the test, place the answer sheet inside the test paper and HAND
BOTH IN.

Page 1 of 4

Part I (20 marks) - Multiple Choice Questions (2 marks each)

Jasmolin II is a pyrethrin compound that occurs in the seed cases of the perennial plant
pyrethrum (Chrysanthemum cinerariaefolium). Pyrethrins have been used as insecticides for
thousands of years and are considered to be of low toxicity from a human health standpoint.
Questions 1 to 10 are about jasmolin II. Choose the correct option for each question.
C2

jasmolin II

C1

O
O

O
O
O1

1. The number of carbon atoms that are best described as being sp3-hybridized is
(a) 9
(b) 10
(c) 11
(d) 12
(e) 13
2. The number of primary carbon atoms present in jasmolin II is
(a) 2
(b) 3
(c) 4
(d) 5
(e) 6
3. The number of pi bond electrons in the compound is
(a) 10
(b) 12
(c) 14
(d) 16

(e) 18

4. The stereochemistry of the double bond contained in a ring and the carbon atom C1 is best
stated by the descriptors
(a) Z, R
(b) Z, S
(c) E, R
(d) E, S
(e) none of (a), (b), (c) or (d)
5. The number of ester functional groups contained in jasmolin II is
(a) 0
(b) 1
(c) 2
(d) 3
(e) 4
6. The source(s) of strain within the jasmolin II molecule is/are
(a) steric strain (b) angle strain (c) torsional (eclipsing) strain
(e) none of (a), (b) or (c)

(d) all of (a), (b) and (c)

7. Which of the following terms best describes the relationship between the two methyl groups
attached to the carbon atom labelled as C2?
(a) trans (b) eclipsed
(c) cis
(d) staggered
(e) none of (a), (b), (c) or (d)
8. The oxygen atom labelled O1 in jasmolin II can act as a
(a) Brnsted base (b) Lewis acid
(c) Lewis base
(e) both (a) and (b)

(d) both (a) and (c)

9. Which of the following terms is an incorrect description of the jasmolin II molecule?

(a) aromatic (b) saturated (c) a hydrocarbon (d) acyclic (e) all of (a), (b), (c) and (d)
are incorrect
10. The compound is likely to be soluble in which of the following solvents?
(a) diethyl ether
(b) H2O (c) hexane
(d) two of (a), (b) and (c)
(e) all of (a), (b) and (c)
Page 2 of 4

Part II. Short Answer Questions

1. (12 marks) Draw appropriate skeletal structures for each of the following molecules. Note
no credit will be given for drawing either condensed or Kekul structures for each part
of this question.
(a). two carboxylic acid constitutional isomers of molecular formula C4H8O2
(b). trans-1-ethyl-2-methylcyclopentane
(c). the compound formed by monochlorination of an alkane that has one quaternary and four
primary carbon atoms (the alkane molecular formula is C5H12)
2. (12 marks) When a strong base is added to the compound below, several monoanions could
theoretically be formed by deprotonation at different atoms.
H3C

HO

OH

NH2

(a). Draw the separate structures of the three monoanions most likely to be formed.
(b). In practice, the monoanion that is actually formed has a formal negative charge on a
heteroatom directly attached to the benzene ring. Draw three additional contributing
resonance forms of this monoanion, and draw two electron flow arrows on one resonance
form only to show how it is related to a second additional resonance form. Lone pairs of
electrons should be included on all resonance forms.
3. (16 marks)
(a). Complete the partial Newman projection template on the answer sheet to represent the
lowest energy conformation of 2-fluoro-2-methylhexane, looking from C3 to C2. Use the
following abbreviations where necessary: H = hydrogen, Me = methyl, Et = ethyl,
Pr = n-propyl, iPr = isopropyl, Bu = n-butyl.
(b). Complete the partial Newman projection template on the answer sheet to represent the
highest energy conformation of 2-fluoro-2-methylhexane, looking from C3 to C2 and using
the same alkyl group abbreviations as in 3.(a)).
(c). Using the provided templates and skeletal structure convention, and clearly showing
substituent orientation, draw the least stable and the most stable chair conformations of
cis-1-n-butyl-4-tert-butylcyclohexane. Note that C1 has been defined in each
conformation.
4. (10 marks) On August 12th 2015, a chemical explosion in Tianjin, China killed over 100
people. One substance involved was calcium carbide (CaC2) which contains the carbide
dianion (C22-).
(a). Draw a Kekul structure for the carbide dianion, being sure to include any lone pairs of
electrons and formal charges on atoms where appropriate.
(b). The carbide dianion reacts with water to form ethyne (acetylene) in two steps. The
organic product at the end of the first step is an acetylide anion (HC2-). Write a balanced
equation and draw appropriate curved arrows to indicate electron flow in the reaction between
the carbide dianion and water to form HC2-.
(c). For the second step, write a balanced equation and draw appropriate curved arrows to
indicate electron flow in the reaction between HC2- and water to form ethyne.
------ END OF TEST -----Page 3 of 4

Periodic Table For Term Test #1

H
3

Y
1

strain energy of one H-Y 1,3-diaxial interaction

Y
-F
-Cl
-Br
-OH
-CH3
-CN

kJ/mol
0.5
1.0
1.0
2.1
3.8
0.4

Y
-CH2CH3
-CH(CH3)2
-C(CH3)3
-C6H5
-COOH

Page 4 of 4

kJ/mol
4.0
4.6
11.4
6.3
2.9