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Chemistry 261 Section A1

Practiced mid-Term Examination

Dr. Sai Yiu

CCIS L2-200
First name Last name

Name________________________________________________

Student ID Number

 Answer all questions. Please note that answers written in pencil or using white-out
are not eligible for re-grading
 Write answers in the spaces provided
 Only answers written on the front side of the page will be marked.
 Should you need extra pages, you may request for an overflow sheet.
 A data sheet is provided

Question Maximum Marks

Number Marks obtained
1 12

2 10

3 10

4 17

Total 49

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1 a) The following diagram is a peptide molecule. amide

0am
foamy
0
carboxylic
E N
amin 0
amine faith
benzyl
o carbonyl
H O

t.es iii
Circle and label all functional groups.

Circle all secondary and primary carbons. ii 1299

b) Use curved arrows, draw all resonance structures for the following two compounds and hence state
which one is the major resonance form for each of them. Briefly explain your reasoning.
given
3 double
his G
resonance
many
can that

hIfN
H
A
1am
H
off.fm
2 a) Which of the following cannot act as a Lewis base?
cannot
(CH3CH2)3N H2 O CH4 CH3OH

NO LP

e
No lone Pair can't donate
2

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b) Which of the following is the strongest acid? Briefly explain.

Fluorine
is
the most

O ELIM
Strongest acid:
Explanation: Achlorine compared
is much stronger higher EN
to fluorine is stronger than because
the chlorine is closer to the COOH
group
has more induction
c) Given the following pKa values:

Complete the following equations by drawing their products with electron-pushing arrows. Predict
whether the reactions will proceed.
WA resultedin stronger date favourable no
n N H to
25 4s
an CH3CHzO t
17 a
Me
CHCHÉ CHzCH3
17 D 50

are favourable if a weak acid always

reactions 1ft start off
a much stronger
acid withgranger
resulted in
favourable
mn goes from stg 3tweak
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3 a)

OH CH
Ceo

From the infrared spectrum provided, identify the functional group(s) that may be present. Be sure to indicate
whether the compound has saturated or / and unsaturated carbon. Make sure you fill the table provided below:

Interpret all relevant absorption peaks to support your choice.

Absorption frequency (cm-1) Interpretation

Possible functional group(s) for spectrum 1:

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CN
CH GO

Interpret all relevant absorption peaks to support your choice.

Absorption frequency (cm-1) Interpretation

Possible functional group(s) for spectrum 2 are:

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4 For the following pair of compounds, state whether they are:

 Constitutional isomers,
 Identical structures,
 Resonance structures or
 No relationship.

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