Organic Chemistry I (CHM 241)- Summer 2018

Practice Exam – Final (100 points)

(The Department of Chemistry, Physical and Natural Science Division, Loudoun Campus
(NOVA))

Student Name:
Student ID number:
Signature:

Please look over entire examination before starting. There are 2 parts. Part I contains multiple
choice questions. Part II contains short answer questions. Answer to all the questions in part I and
part II. Make sure to submit all the papers you used during the examination including exam
questions and the scratch papers if you have used any. Be sure to write your name on each paper
you submit.

Part I (20 points)

Circle correct answer
1. Formal charges of the shown atoms of the given molecule are:
A
O

B
C

a) A=0, B=0, C=0

b) A=+1, B=0, C=0
c) A= -1, B=0, C=0
d) A=+1, B=+1, C=0
 2. How are the molecules in the following pair related?
OH

a.) They are enantiomers

b.) They are diasteriomers
c.) They are constitutional isomers
d.) They are stereoisomers

3. Which molecule is more acidic?

O O

OH OH
Cl

A Cl B

a.) A
b.) B
c.) Both A and B have the same acidity
d.) Data are not enough to decide

4. IUPAC name of the given molecule:

Cl

a.) 4-chloro-1-isopropyl-4-methylcyclohex-1-yne
b.) 4-chloro-1-isopropyl-4-methylcyclohexane
c.) 1-chloro-4-isopropyl-1-methylcyclohex-4-ene
d.) 4-chloro-1-isopropyl-4-methylcyclohex-1-ene
5. Which of the following statement is true?
a) SN2 reaction is bimolecular, and faster in aprotic solvent
b) SN1 reaction is bimolecular and faster in protic solvent
c) SN1 reaction mechanism is stepwise and faster with primary alkyl halide
d) SN2 reaction mechanism is concerted, bimolecular, and faster with tertiary alkyl halide
 6. Major product of the given reaction would be:

H2SO4/ H2O

OH
OH

HO

A C
B

a) A
b) B
c) Both B and C would have the same amount
d) A mixture of all the above
7. Hybridization of the carbon atom indicated by arrow is
O

a) sp2
b) sp3
c) sp
d) None of the above
8. Product of the following alkyne when it is treated with Lindlar’s catalyst?

A B C

a) A
b) B
c) C
d) A mixture of all the above
9. According to the energy diagram below:

a) This reaction should be endothermic

b) This reaction should be exergonic
c) This reaction should be endogonic
d) Data are not enough to decide
10. Which of the following is a primary alkyl halide?
H Br
Cl

Br
H H
H

A B C

a) A
b) B
c) C
d) All of the above
Part II Short answer question
1. Label the following as R or S (5 points).

2. Provide IUPAC name of the following molecule (5 points).

OH
HS
3. A student was asked to synthesis molecule A. She/he performed the following reaction and
was told that that pure (R)-2-bromo-1-phenylpropane has an [α]25 = +25º. (10 point s)

Reaction:

[α]25 = -20º

a. What is the enantiomeric excess of the starting material?

b. Draw the starting material below with the correct absolute configuration at the
stereocenter.
c. Draw a mechanism for the reaction clearly showing the product’s stereochemistry:

d. Write the rate law for the reaction.

4. Complete the following syntheses. Three arrows indicate that more than one step may be
necessary (They do not indicate the number of steps…could be one, two, three, or more) (10
points):
O O
a) H H
OH

Br
b)
O
5. Indicate the product(s) for the following reactions. Circle major product. Also indicate if the
reaction proceeds by an SN1, SN2, E1, or E2 reaction and give the stereochemistry where
appropriate. (15 points)

a. Br
NaI

b. OH
Conc. H2SO4

Heat

c. KOC(CH3)3
Br
CH3CH2OH

Cl NaOMe
d.
MeOH

OH 1. xs NaNH2
e.
2. CH3CH2Br
6. Provide regent or starting material, or product for the given reaction (10 points):

a)

HO Br HO Br

H H + H
b)

Br Br
Br2
+
c)
Br Br

Br
d) Br

7. Suggest a mechanism for the following reaction (5 points)

OH
1. Hg(OAc)2, H2O

2. NaBH4
8. Identify the relationship in each of the following pairs as enantiomers, diastereomers,
identical, constitutional isomers or meso compounds. (10 points)

a.

OH
H
H
b. OH

c. Cl Cl

H OH
d.
HO H

9. Clearly indicate the number of steps, intermediates, transition states of the reaction shown by
each the following energy diagram (potential energy vs reaction progress) (5 points)
10) Rank the following from most to least stable. Simply explain your ranking (5 points)

A. B. C.

Bonus (5 points)
a) From the given bonds, which of bond stretching frequencies has higher frequencies?
Simply explain the reasoning.
i. C-H or C-O

ii. N-H or O-H

iii. C-C or C=C