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THE UNIVERSITY OF TORONTO

CHEMISTRY 136H
Introductory Organic Chemistry I

Term Test 1

PRACTICE TEST

Instructions:

• You have 90 minutes. Keep this test booklet and the answer booklet closed and face up
on your desk until the start of the test is announced.

• You may use a molecular model kit (pre-assembled molecules are allowed) and a non-
programmable calculator.

• The test consists of 10 multiple choice questions worth 2 marks each (20 marks total)
5 short answer questions, with multiple parts (50 marks total), for a total of 70 marks.

• This test booklet consists of 4 double-sided pages (8 pages in total) and includes ALL of
the test questions, a periodic table, spectroscopic tables, and blank pages for rough work.
You may detach the pages of the test booklet. Nothing in this booklet will be graded but
must be handed in.

• The answer booklet consists of 2 double-sided pages (4 pages in total):

o Page 1 Cover sheet: Clearly, in BLOCK LETTERS write your FULL NAME and
STUDENT NUMBER in the provided spaces.

o Pages 2-3 Answers to the short answer questions: Write your answers clearly
and concisely in the boxes provided. Write in PENCIL and use an ERASER as
needed so that you can fit your final answer in the appropriate space.

o Page 4 Multiple Choice answer sheet: Write your name and student number at
the top of the sheet and clearly bubble in your answers for the multiple-choice
questions.

• At the end of the test, stop writing when instructed and remain seated until all test
papers have been collected. All papers will be collected, including rough work. Please
stack your answer sheets on top of the question sheets. DO NOT PLACE THE ANSWER
SHEETS INSIDE THE QUESTION SHEETS.




GOOD LUCK!
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Part A – Multiple Choice Questions (20 marks: 10 questions, 2 marks each)

Levomenol is an active ingredient in chamomile and has been used in cosmetics for
hundreds of years.

Questions 1 to 6 pertain to this compound.

1. How many hydrogen atoms does
levomenol contain?

a) 24 b) 25 c) 26 d) 27 e) 28


2. The sigma bond between the carbons atoms labeled with an arrow is best described as
being formed by the overlap of which type of orbitals?

a) C sp3 – C p b) C sp2 – C sp2 c) C sp3 – C sp3 d) C sp2 – C sp3 e) C sp2 – C sp


3. What is the approximate C-C-C bond angle labeled "a"?

a) 90° b) 109° c) 120° d) 150° e) 180°


4. The alcohol functional group in levomenol is best described as:

a) primary b) secondary c) tertiary d) quaternary e) trans


5. Which of the following statements is/are true?

i) Levomenol is more soluble in hexanol (C6H13OH) than in water.
ii) Levomenol can have hydrogen-bonding interactions.
iii) Levomenol contains only non-polar bonds.

a) i only b) ii only c) iii only d) i and ii only e) i and iii only

6. In the 1H NMR spectrum of levomenol, how many unique signals would integrate to 1 H?

a) 1 b) 2 c) 3 d) 4 e) 5

7. Which of the following molecules have net dipole moments?



a) i only b) ii only c) iii only d) two of i, ii and iii e) i, ii and iii


levomenol

a
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8. How many 1H-NMR signals are expected for the amino acid,
threonine, shown here?



a) 4 b) 5 c) 6 d) 7 e) 8

9. Which of the following structures is 4-bromo-3-isopropyl-7-methyloct-6-enal?

a) b) c)
d) e)


10. Which compound does this IR spectrum represent?


a) b) c)

d) e)

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Part B – Short Answer Questions (50 marks each)

1. (10 marks)
a) Draw an appropriate line structure for the following molecule. Note – no credit will be
given for drawing molecules using any other structure types (e.g. condensed
structures). Use the template provided on the answer sheet.

7-(tert-butyl)-6-fluoro-3,3-dimethyldecan-2-ol

b) Rank the following molecules in order of increasing boiling point (from lowest to
highest).



Provide a brief explanation for your rationale (20 words or less).


2. (9 marks) Consider the structure shown below:



a) On the answer sheet, draw the TWO next best resonance forms that contribute to the
description of the bonding in the ion shown above. All lone pairs of electrons must be
included on all resonance forms. Be sure to include formal charges where
appropriate.

b) Draw electron flow arrow(s) on resonance form A to show how it is related to resonance
form B. Then, draw electron flow arrow(s) on resonance form B to show how it is related
to resonance form C.

c) Of the three resonance forms (including the one provided), circle the most important
contributor to the resonance hybrid.






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3. (13 marks) Consider the substituted cyclohexane, shown below:



On the answer sheet…

a) Draw the least stable chair conformation. Include ALL substituents, including all
hydrogen atoms.

b) Identify any 1,3-diaxial interactions with curved double headed arrows (see example
below) on your conformer.


c) Draw a cis-trans isomer of the substituted cyclohexane shown above that exhibits no
CH3-CH3 1,3-diaxial interactions in its most stable conformation.


4. (10 marks)
a) Compound X has a chemical formula of C5H10O2, and produces the following IR and 1H
NMR data, shown below. Propose a structure for compound X.


1H NMR Spectrum (integrations shown above each signal):


IR data: 1735 cm-1 (strong, sharp)


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b) Consider the constitutional isomers, A and B, below. List 2 differences you would expect
to see in their 1H-NMR spectra. Include relevant information such as number of signals,
chemical shift values (ppm), integration values, etc.

Isomer A: Isomer B:


5. (8 marks) On the answer sheet, complete the Newman projections for
1,1-dichloro-4-methylpentane, sighting along the C1-C2 bond from C1 (front) to C2
(back). Each labeled Newman projection must correspond to the energies A, B, C and D on
the diagram below.

Use the following abbreviations as needed for different groups: H = hydrogen, Me = methyl,
Et = ethyl, nPr = n-propyl, iPr = isopropyl, nBu = n-butyl, iBu = isobutyl, tBu = t-butyl.


D
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IR Spectroscopy Table

Functional Group Wavenumber (cm-1) Functional Group Wavenumber (cm-1)
O – H (alcohols) 3200 – 3600 (s, b) C – N 1180 – 1360 (w)
O – H (acids) 2700 – 3200 (s, b) C Ξ N 2110 – 2260 (m)
N – H 3300 – 3500 (w, b)

C – H (sp3) 2800 – 3000 (s) C – O 1080 – 1300 (s)
(sp2) 3000 – 3100 (s) C = O (carboxylic acid) 1710 – 1800 (s)
(sp) 3300 – 3325 (s) (aldehyde) 1720 – 1740 (s)

(ketone) 1708 – 1720 (s)
C = C (alkene) 1640 – 1680 (m) (ester) 1735 – 1750 (s)
C Ξ C (alkyne) 2100 – 2260 (w) (acid chloride) 1785 – 1815 (s)
C=C (aromatic) 1500 – 1600 (m) (acid anhydride) 1740 – 1870
(s, 2 peaks)

(amide) 1626 – 1786 (m)








s = strong, m = medium, w = weak, b = broad
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1H NMR Spectroscopy Table

1H NMR Chemical Shifts
Type of Proton Chemical Shift (ppm)
RC–H alkane 0.9 – 1.7
C=C–C–H allylic 1.7 – 3.0
O=C–C–H α-proton 1.8 – 2.2
Ar–C–H benzylic 2.2 – 2.5
C≡C–C–H propargylic 1.7 – 2.8
C≡C–H alkynyl 2.0 – 3.0
X–C–H X = O, N, halide 2.5 – 4.8
C=C–H vinylic 4.0 – 7.0
Ar–H aromatic 6.5 – 8.5
RCHO aldehyde 9.0 – 10.0
O–H, N–H alcohol, amine 1 – 5 (broad)
COOH carboxylic acid 10 – 13 (broad)


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