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CH203 Fall 2014 Exam Two Practice Test



10/27/14

1. How many sets of equivalent protons are there in hexane?
a. 2
b. 3
c. 6
d. 7



2. Which of the following combinations of peaks appears in the
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H NMR spectrum of butane?
a. a triplet and a doublet
b. a triplet and a quartet
c. a triplet and a sextet
d. two singlets

3. Which C
4
H
9
Br compound gives a triplet at approximately 3.5 ppm in the
1
H NMR spectrum?



a. 1
b. 2
c. 3
d. 4

4. How many signals appear in proton-decoupled
13
C NMR spectrum of 3,4-dimethylhexane?
a. 3
b. 4
c. 5
d. 6

5. Which of the protons in the following molecule appear at the highest -value in the
1
H NMR spectrum?



a. i
b. ii
c. iii
2
d. iv

6. How many signals appear in the proton-decoupled
13
C NMR spectrum of 2-bromotoluene?
a. 3
b. 4
c. 5
d. 7

7. Which C
4
H
9
Br compound(s) gives a
13
C NMR spectrum consisting of four signals?



a. only 1
b. only 1 and 2
c. only 2 and 3
d. 1, 2, 3 and 4

8. Which of the following compounds gives a
1
H NMR spectrum consisting of two singlets and a
13
C NMR
consisting of consisting of three signals?



a. only i
b. only iii
c. only ii and iii
d. only ii, iii and iv

9. The chemical shift of the protons of acetone, CH
3
COCH
3
, is 2.1 ppm when the spectrum is obtained at 250
MHz. What is the chemical shift of these protons when the spectrum is acquired at 500 MHz?
a. 1.05 ppm
b. 2.1 ppm
c. 4.2 ppm
d. 8.4 ppm

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10. Which of the following compounds gives a
1
H NMR spectrum consisting of only a singlet, triplet and
quintet?
a. CH
3
OCH
2
CH
2
CH
2
CH
2
OH
b. CH
3
OCH
2
CH
2
OCH
2
CH
3

c. CH
3
OCH
2
CH
2
CH
2
OCH
3

d. CH
3
OCH
2
CH(CH
3
)OCH
3


11. Which of the following compounds have enantiotopic protons?

1. propane
2. butane
3. 2-methylpropane

a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3

12. Which of the following is true for pair of diastereotopic protons?

1. They will appear at the same chemical shift in an achiral (i.e., nonchiral environment)
2. They will appear at the same chemical shifts in a chiral environment

a. only 1
b. only 2
c. neither 1 nor 2
d. both 1 and 2

13. Which C
6
H
12
O
2
compound gives the following
1
H NMR spectrum?

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a. 1
b. 2
c. 3
d. 4

Consider the following structure. Answer the following questions by placing the appropriate number in
the blank to the left.


14. _____The number of nonequivalent hydrogen atoms in this compound.


15. _____The number of signals in the hydrogen-decoupled
13
C NMR of this compound.


16. _____The number of nonsinglet splitting patterns in the
1
H NMR of this compound.


17. Identify the compound (C
8
H
10
) that gives the following
1
H NMR spectrum.
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18. Identify the compound (C
8
H
11
N) that gives the following
1
H NMR spectrum.



19. Identify the compound (C
8
H
10
O
2
) that gives the following
1
H NMR spectrum.



20. What is the IUPAC name of the following compound?

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a. (R)-2-bromo-2-vinylpentane
b. (S)-2-bromo-2-vinylpentane
c. (S)-3-bromo-3-propyl-1-butene
d. (R)-3-bromo-3-methyl-1-hexene


21. Which of the following bonds has the lowest bond dissociation enthalpy?
a. CH
b. CF
c. CBr
d. CI

22. What is the major organic product obtained from the following reaction?



a. 1
b. 2
c. 3
d. 4

23. What is the major organic product obtained from the following reaction?



a. 1
b. 2
c. 3
d. 4

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24. What is the correct order of stability of the following radicals (more stable > less stable)?



a. 1 > 2 > 3
b. 2 > 1 > 3
c. 2 > 3 > 1
d. 3 > 2 > 1

25. What is the characteristic of a radical chain propagation step?
a. Radicals are formed.
b. Byproducts are formed.
c. A radical reacts with a molecule to give a new radical and a new molecule.
d. Two radicals combine to give a molecule.

26. What type of reactive intermediate is formed upon irradiation of a solution of toluene (PhCH
3
) and
bromine?
a. benzylic carbocation
b. benzylic carbanion
c. benzylic radical
d. cyclic bromonium ion

27. Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the
major product?



a. 1
b. 2
c. 3
d. 4

28. What is the major product formed upon radical bromination of (S)-3-methylhexane?
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a. (S) 3-bromo-3-methylhexane
b. (R) 3-bromo-3-methylhexane
c. a mixture of (R) and (S) 3-bromo-3-methylhexane
d. (3R) 1-bromo-3-methylhexane

29. Which of the following statements is not true about the allyl radical
a. The carbon-carbon bond lengths are identical.
b. The unpaired electron density is shared between carbons 1 and 2.
c. It undergoes reaction with bromine to give a single product.
d. It is formed by abstraction of a hydrogen atom from the methyl group of propene.

30. How many electrons does the allyl radical have in p orbitals
a. 1
b. 2
c. 3
d. 4

31. Which of the following is an accurate statement of Hammond's postulate?
a. The transition state of an exothermic reaction will resemble the starting materials
(reactants) more than the product.
b. The transition state of an exothermic reaction will resemble the products more than the
starting materials (reactants).
c. The transition state of an endothermic reaction will resemble the starting materials
(reactants) more than the product.
d. the difference in energy between the starting materials (reactants) and transition state
controls the rate of a reaction.

32. What type of reactive intermediate is formed in the reaction of propene with hydrogen bromide in the
presence of peroxides to give 1-bromopropane?
a. 1 radical
b. 1 carbocation
c. 1 radical
d. 2 radical

33. What is the major organic product obtained from the following reaction?



a. 1
b. 2
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c. 3
d. 4

34. What are the major products formed upon treatment of (E)-3-methyl-2-hexene with HBr in the presence of
peroxides?

1. (S,S)-2-bromo-3-methylhexane
2. (S,R)-2-bromo-2-methylhexane
3. (R,S)-2-bromo-2-methylhexane
4. (R,R)-2-bromo-2-methylhexane

a. only 1 and 2
b. only 1 and 4
c. only 2 and 3
d. a mixture of 1, 2, 3, and 4

35. What are the structures of all of the monobrominated products, including regioismers and stereoisomers,
obtained from the following reaction?




36. What is the structure of the key intermediate in the following reaction?



37. During bromination using NBS, the concentration of bromine remains ________throughout the course of the
reaction.


38. The number of possible monobromination products, including cis-trans isomers, of
methylcyclopentane is ______.


39. The number of possible dibromination products of 2-methylpropane is______.


40. The number of possible monobromination products of cyclopentane is______.