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Exam#1

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17 views6 pages

Exam#1

Uploaded by

ZuYu Mei
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Exam #1

This test is timed. You will have two hours to complete the test. Read each
question carefully and answer all of them.

Answer all the questions either on the Test itself or on a separate sheets of
papers (use your own) and upload as one pdf attachment in the blackboard.
Answer all the questions. Total 100 points
1. a) Draw one Lewis structure including lone pairs, one line angle formula and
one condensed structure for the following compound. (6 points)
C6H12NOCl

b) Draw the Resonance structures and show arrows for the following
structures (8 points)

i)

ii) O

iii) O

O
iv) N

1
c) Indicate the following reactants as nucleophile and electrophile and draw
curved arrow that leads to the products . (8 points)

Cl
N Na +
H

2. a) Arrange the following compounds in the order of increasing boiling points.


Use intermolecular forces to figure out. (6 points).

OH
a) b) c) d) e)

Cl

b) Indicate hybridization on each carbon for the following compound (4 points).


2 4
6

3 5

c) Circle and write the name for the four different functional groups present in the
following drug. (8 points)

O
HO HO O OH OH

H 2N
H
O H
N OH

2
3. a) Give the IUPAC names for the following compounds. Don’t use common
names such as isopropyl, tertiary butyl. (8 points)

i) ii)

CH2CH3
iii) iv)
Br
Br
CH3

b) Draw the structures (use line angle formula or Lewis structure) for the
following compounds. Don’t use common names such as isopropyl,
tertiary butyl. (6 points)

i) 1-bromo-2-chloro-5-(1’, 1’-dimethylethyl)cyclohexane

ii) 3-(1’-methylethyl)-2,5-dimethylhexane

iii) Draw cis and trans isomers for 1-ethyl-2-methylcyclopentane.

3
c) Draw Newman Projections and energy profile between dihedral angle and
potential energy for butane as it rotates about the bond between C2 and C3.
Draw the Newman projections for all the possible conformations from 00
to 3600. (12 points)

d) Draw the two chair conformations for trans-1,2-dimethylcyclohexane


and label all the carbons clearly as equatorial and axial. Label the most stable
and least stable chair conformation and explain the reason. (8 points)

4
e) Why cyclohexane is more stable than cyclopropane, cyclobutene,
cyclopentane. Indicate two reasons and explain clearly. (8 points)

4. a) Arrange the following carbon radical intermediates in the order of


increasing stability (least stable to most stable) and give two reasons. (4 points)

CH3
1 4
2 3

5
b) Write a step-by-step mechanism using half arrows and draw reaction-
energy profile diagram (two curves for minor and major products) for
the first and second propagation steps when propane (CH3CH2CH3) reacts
with chlorine (Cl2) under light initiated condition. Label the parts that
represent the reactants, intermediates, transition states, and activation
energy. What is Hammond postulate for this reaction?
(14 points)

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