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Exam 3 Name CHEM 261-01

Turn in your exam in my office physically between 8:01 am and 10:59 am, on
Monday May 01,2017 (100 pts)
1. Which of the following reactions is likely to fail? 3 pts

a. Reaction of sodium cyanide with 1-Iodo-4-methylcyclohexane

b. Reaction of sodium cyanide with 1-Iodo-1-methylcyclohexane
c. Reaction water with 1-Iodo-4-methyl-cyclohexane
d. Reaction of sodium tert-butoxide with 1-Iodo-4-methylcyclohexane

2. Which of the following reaction is likely to be the fastest? 3 pts

a. Reaction of sodium cyanide with 1-Iodo-4-methylcyclohexane

b. Reaction of sodium cyanide with 1-bromo-3-methylcyclohexane
c. Reaction of sodium cyanide with 1-bromo-4-methylyclohexane
d. Reaction of sodium cyanide with 1-iodo-1-methylcyclohexane

3. The reaction of potassium ethoxide with the molecule below fails. Explain why?
3 pts

Br
H
H

4. The compound below fails to give only one product. Draw all the organic product(s)
of the reaction and state why not only one product can be formed?
6 pts

CH3OH

H+ catalyst
OH

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)

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5. Draw the following compounds. 6 pts

a. (5R, 6R)-5-Chloro-3,6-dimethyl-2-octene

b. Cis - 3-Ethyl-5-isopropyl-4-methylcyclohexanol

6. CIRCLE ALL of the molecules that are NOT susceptible to oxidation. 3 pts

O O
OH HO O
H

7. Label the compounds below as aromatic/anti-aromatic/non-aromatic? 16 pts

O
N
NH
N N
O H

HN

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)

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8. Predict the major organic product expected from the reaction sequence below?
6 pts

I
NaOCH3 RCOOOH

1. NaSH
2. H+

9. Arrange the compounds below in order of reactivity towards Friedel Crafts alkylation
using the following scale: 1 = least reactive, filled in the small boxes below the
molecules. If you have same ranking use same numbers? 12 pts

O OH
OCH3 SO3H F Br

10. DRAW three resonance structures for the cation intermediate of the (EAS)
bromination of phenylammonium salt below? 6 pts

NH3

Br+

resonance 1 resonance 2 resonance 3

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)

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11. Predict the major product(s) expected from the reactions below. 18 pts

Cl
FeBr3
+ Br2

HO

HNO3
HO
H2SO4

H2Cr2O4
OR
KMnO4,Heat
then H+

Cl AlCl3
NC +

O conc. H2SO4
+

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)

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12. Predict the major organic product(s) expected from the reactions below. Also
indicate the type of reaction? 18 pts

a) I + NaOMe
EtOH, 50oC

Type of reaction?

Br + NaSH
b)
acetone

c) Br t-BuOK
t-BuOH, 50oC

Type of reaction?

I
d) EtO-
EtOH, 50oC

Type of reaction?

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)

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CH3CH2OH
e) Br

Type of reaction?

NaCN
f) Cl H Br
O

Type of reaction?

CHEM 261-01 Exam 3 Spring 2017 (Dr. Ihachi, Moses)