CHEMISTRY DEPARTMENT

UNIVERSITY OF BOTSWANA

CHE 232: STRUCTURE AND SURVEY OF FUNCTIONAL GROUPS I

(ORGANIC CHEMISTRY)

TEST ONE

TIME ALLOWED: 2 HOURS 16th September 2015

Student ID No.:…………………………..Surname and Initials:.………………………….

1. Answer ALL the questions

2. You are allowed to use molecular models

3. WRITE ALL ANSWERS IN INK

The paper has 11 printed pages

DO NOT WRITE IN THIS TABLE

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

2. What is the IUPAC name for the following compound?

a. 1,3-pentamethylpropane

b. 1,1,3,3-tetramethylbutane

c. 2,4,4-trimethylpentane
d. 2,2,4-trimethylpentane

3. The following reaction occurs as part of the mechanism of the formation of

chloroethane from the reaction of ethane with chlorine in the presence of
light. In which mechanism step does this reaction occur?

a. Initiation
b. Propagation
c. Termination
d. Both Termination and Initiation

4. Which one of the following structures would be named, (2Z,4E)-hepta-2,4-diene?

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5. Which of the following Newman projection formulas represents 2, 4-dimethylhexane ?

6. The compounds represented by the following structures are

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?

a. NH2 > I >CH3 >H b. H > I >CH3 > NH2

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?

a. 2-methylbut-2-ene is more stable than but-1-ene

b. but-1-ene gives two products
c. 2-methylbut-2-ene forms a more stable carbocation intermediate than but-1-
ene
d. But-1-ene is not soluble in acid

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?

16. Which of the following statements is incorrect?

a. The major product of the electrophilic addition of HBr to 1-hexene is 2-bromohexane
b. In the presence of a radical initiator, HBr reacts with 1-butene to give 1-bromobutane
as the major product
c. In the presence of a radical initiator, HBr reacts with 1-butene to give a
Markovnikov addition product
d. The electrophilic addition of HBr to 2-butene involves a secondary carbocation
intermediate

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17. What is the structure of the intermediate product X obtained in the hydroboration-
oxidation reaction of vinylcylohexane?

18. Which of the following pair(s) of compounds are keto-enol tautomers?

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

Answer all questions in this section (60 marks).

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:

Combination of any two radicals

(iii) Propose a plausible mechanism for the following transformation. [5 marks]

(iv) How would you synthesize propanone from ethyne? [5 marks]

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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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