CHEM

2OA3 – Summer 2017

Assignment 1;
Due: Friday May 19, 2017 at 4:00 pm
NAME:____________________________ ID#:__________________________

Lab Bench (2-72, NOT L01, L02 etc):_____ (On Avenue in grade book)
Please circle your lab section:
Lab Group Tuesday Wednesday Thursday
am L01 L03 L05 Exempt
Lab
pm L02 L04 L06
Tutorial T01 T02 T03

[-2] Marks for not completing ALL of the above information correctly Total marks: 100

Students’ Responsibility:

1. Answers must be filled in, in the space provided. Show detailed solutions/answers.
Answers written in pencil will be graded, but will not be considered for revised marking.
Only ONE submission per student is allowed!
2. Work submitted in pencil will be graded, but cannot be submitted for mark corrections.
3. NOTE: The drop boxes are located in the corridor close to the chemistry office. You
MUST place your work in the slots designated “CHEM 2OA3/2OB3”, in the CORRECT slot,
FOR THE CORRECT LAB DAY.
4. Any assignment not submitted in the correct place and/or after the due date and time
will be graded zero.
5. Students who cannot complete the assignment for medical or other reasons MUST seek
exemption through an MSAF, a note from the appropriate Dean’s office or other
accepted routes.
6. You are responsible for ensuring that your print-out is complete and that all questions
are answered. There are 10 pages and 9 questions in this assignment

Question: #1 #2 #3 #4 #5 #6 #7 #8 #9 TOTAL
Out of: 10 10 9 14 6 11 7 13 13 93
Marks:

1
 1. Jaborosalactone A is a naturally occurring steroid with some antitumor activity and insect
antifeedant properties. It was isolated from the plants of Solanaceae family.

On the following structure, name all the functional group that are circled.
Be specific and avoid general terms. (9 marks)

OH

O O
O

H H

O


How many methyl groups are present in this compound? ____________ (1 mark)

2

2. A chemist used the following sequence of reactions to prepare compound E. Provide the
structures for each of the intermediates A, B, C, and D, in the spaces provided, and provide
a structure for the target compound E. (E has a very strong band in the IR spectrum at
1745 cm–1). (10 marks)

O
1. LiAlH 4, Et 2O SOCl2, Py

2. NH 4Cl, H 2O
A B

Mg, Et 2O

EtOH 1. CO2(s)
H 3O+
2. H 3O+
D C
E

3
base for Organic Compounds,SDBS 2017-04-24, 6*16 PM

3. Shown below is the infrared spectrum of an unknown organic compound that contains a
ation single functional group that comprises oxygen. Answer the questions below about the
spectrum (Be specific about functional groups, not just ‘carbonyl’) (9 marks)

a: C8H8O2

136.1

e
Web (on trial since

l3
in CDCl3

r in acetone-d6
a. CIRCLE the functional groups in the list below that could be present based on the
above information:
0 M,liquid
on:
Ketone Ester Ether Aldehyde Alcohol Carboxylic acid

b. CIRCLE the functional groups in the list below that are NOT present based on the
above information

pound: Ketone Ester Ether Aldehyde Alcohol Carboxylic acid
ist.go.jp/sdbs/cgi-
_disp.cgi?sdbsno=725
c. What structural information can be deduced from peak at 1278 cm–1?



d. What structural information can be deduced from the peaks just below 3000 cm–1?

4
 4. Draw bond-line structures with dashes and wedges for the following compounds. What is
the hybridization of the highlighted atoms? (14 marks)
a. CH3CH=CH2
b. (CH3)3N
c. CClF2H
d. (CH3)4N+
e. CH3C≡CH
f. CH3OH2+
g. PH3

5
 5. (a) Draw all resonance structures of comparable energy for the following isomeric species
(A and B are the ionized forms of the same compound):
(3 marks)

O O
O S O O S OH

OH O

A B









(b) Based on your answer to part (a), which of the two structures above will be present in
higher concentration in an aqueous solution at pH 7? (3 marks)

6
 6. Fully explain why ethanol (pKa 16) and phenol (pKa 10) are less acidic than acetic acid (pKa
4.74). (Tip: draw resonance structures for the anions, compare their contributions to the
stabilization of the negative charge) (11 marks)

7
rganic Compounds,SDBS 2017-04-24, 8*4

SDBS-Mass
7. A chemistry professor, while working in the lab, found an unlabeled flask containing a
cloudy liquid (bp 100–105 °C). To identify the compound, he ran a quick mass spectrum,
MS-NW-0163 SDBS NO. 1225
which is presented below.
1-bromobutane
C4H9Br (Mass of molecular ion: 136)

al since

Source Temperature: 230 °C
Sample a. Identify the compound?
Temperature: 80 °C (2 marks)
RESERVOIR, 75 eV
/sdbs/cgi-
? peak data

MS-NW-0163 b. Suggest structures for the fragments 136, 107 and 57.
SDBS NO. 1225 (3 marks)
e
National Metrology Institute of Japan(NMIJ)









c. Why is the base peak (m/z 57) is so strong? (2 marks)

8
 8. Substituents in organic molecules can donate or withdraw electron density from carbon
atoms. There are two main types of electronic effects:
a. Inductive effects (±I) – donation or withdrawal of electron density through s bonds
(along the internuclear axis). Inductive effects are represented by straight arrows.
b. Mesomeric (resonance) effects (±M) – donation or withdrawal of electron density
through p interaction, and represented by curved arrows.
Both effects can be negative (–I, –M) and positive (+I, +M). Negative electronic effects
are a result of withdrawal of electron density from carbon atom by substituents.
Positive effects are observed when substituents donate electron density to the carbon
atom.
What types of electronic effects are typical for the groups presented in the table
below? (13 marks)

Functional group Inductive effect: Mesomeric effect:
(+I), (–I) or no I effect (+M), (–M), or no M effect
–O– (alkoxide)

–OH (alcohol)

–COOH (carboxylic acid)

–COO– (carboxylate)

–OR (ether)

–C(CH3)3

–C≡N

–NO2

–COR (ketone)

–Cl

–CH2CH3

–CH=CH2

–C≡CR

9
 9. Draw resonance structures for the following molecules and ions. Identify the type of
the mesomeric (resonance) effect (+M or –M). Note that there can be more than two
resonance structures. Show formal charges and lone pairs where necessary.
(13 marks)

a. Cl

b. Cl

O

c. H

d.

O H

e.

OCH3

f.

O–

g.


O O
N

h.

O

i.

10