CHE 232 Test 1 2015 Ans
CHE 232 Test 1 2015 Ans
UNIVERSITY OF BOTSWANA
TEST ONE
MC 1 2 3 Total
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SECTION A
Answer ALL questions in this section by circling the correct answer in each question. (40
marks, 2 marks each)
1. What is the total number of sigma bonds found in the following compound?
a. 8
b. 10
c. 11
d. 15
a. 1,3-pentamethylpropane
b. 1,1,3,3-tetramethylbutane
c. 2,4,4-trimethylpentane
d. 2,2,4-trimethylpentane
a. Initiation
b. Propagation
c. Termination
d. Both Termination and Initiation
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5. Which of the following Newman projection formulas represents 2, 4-dimethylhexane ?
a. Structural isomers
b. Identical
c. Geometrical isomers
d. Conformational isomers
7. What is the molecular formula of a hydrocarbon that has one triple bond, two double
bonds, one ring and 32 carbon atoms?
a. C32H62
b. C32H60
c. C32H58
d. C32H56
8. According to the Cahn-Ingold-Prelog convention, which priority ranking is correct for the
following sets of groups?
c. I > NH2 > CH3 > H d. I > CH3 > NH2 > H
9. Which of the following statements is true about the species shown below:
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a. W and Y are nucleophiles, whereas X and Z is an electrophiles
b. W, X and Y are nucleophiles, whereas Z is an electrophile
c. W and Y are nucleophiles whereas X and Z are electrophiles
d. W and Z are electrophiles, whereas X and Y are nucleophiles
10. Which one of the following schemes showing the flow of electrons from reagent forming
products is not correct?
11. Why are polar addition reactions of 2-methylbut-2-ene faster than those of 1-butene?
12. What will be the structure of the major product in the reaction shown below?
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13. Cyclohexene is treated with cold dilute alkaline KMnO4. Assuming syn addition, the
spatial arrangement of the two hydroxyl groups in the product would be:
a. equatorial-axial
b. axial-axial
c. equatorial-equatorial
d. coplanar
14. The addition of O3 to a terminal alkene, (e.g. 1-hexene) followed by treatment with
dimethyl sulfide (CH3)2S is a method for preparing
a. Two ketones
b. A 1,2-diol
c. Two aldehydes
d. An aldehyde and a ketone
15. What is the major product expected from the following reaction?
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17. What is the structure of the intermediate product X obtained in the hydroboration-
oxidation reaction of vinylcylohexane?
a. X b. Z c. Y d. Y and Z
19. Which of the following reagents will not yield the given product for the reaction shown
below?
20. What is the major product expected from the following reaction?
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Section B
Question One
(i) Each of the following names is incorrect. By drawing the structure give the correct
IUPAC name for each compound. [10 marks]
(a) 2,2-dimethyl-4-ethylheptane
(b) 3-isopropyloctane
(c) 1-ethylpent-1-ene
(d) (E)-2-methylhex-1-ene
(e) 2-ethylhex-3-yne
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(ii) Sighting along the C2-C3 bond of 2-methylbutane, there are two different staggered
conformations and two different eclipsed conformations.
(a) Draw the Newman projections for the two different eclipsed conformations and indicate
the more stable conformer. [4 marks]
(b) Draw the Newman projections for the two different staggered conformations and indicate
the more stable conformer. [4 marks]
(iii) The barrier of rotation about the C-C bond in bromoethane is 15.0 kJ/mol. If each
hydrogen-hydrogen interaction in the eclipsed conformation is responsible for 3.8
kJ/mol, how much is the hydrogen-bromine interaction responsible for? [2 marks]
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There are 2 H/H interaction and one H/Br interaction
Therefore: H/Br contribution = 15.0 kJ/mol- (2× 3.8 kJ/mol)
= 7.4 kJ/mol
Question Two
(i) Indicate the hybridization of each carbon and give the approximate value of the bond
angle about each carbon for the compound shown below. [4 marks] [1/2 mark each]
(ii) Draw proper curved arrows to complete the reaction mechanism shown below and
give structures of two possible termination products. [6 marks]
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Two possible termination products:
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Question 3
(i) Give the missing reactants, starting materials or products in the scheme below. [16
marks]
(ii) Compound A, was found to have the molecular formula C 10H20, and upon treatment
with (1) O3, then (2) Zn/HOAc yielded 2 mol equiv. of 2-pentanone as the only
product. The same product i.e. 2-pentanone was obtained when 1-pentyne was
treated with water in the presence of acid and mercuric acetate. Deduce the structure
of compound A and hence write the two equations referred to above [4 marks]
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