THE COPPERBELT UNIVERSITY

SCHOOL OF MATHEMATICS AND NATURAL SCIENCES

CH 260 - ORGANIC CHEMISTRY

TEST 1

TIME: THREE (03) HOURS 100 MARKS

INTRUCTIONS TO CANDIDATES

1 There are SIX (06) questions in this paper. Answer ALL questions.

2 Each question carries twenty (20) marks

4 Candidates are reminded of the need for the clear presentation in their answers

5 All the parts of a question should be answered strictly in continuation

2019-2020 CH 260 TEST 1

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QUESTION ONE
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(a) Bond formation in the carbon atom involves the hybridization of S and P orbitals to give SP-
hybridized orbitals. Discuss briefly the hybridization involved in carbon in each of the following
compounds:
(i). CH2Cl2 [2]
(ii). CH N [3]
(b) Write the molecular formular of each of the following alkanes:
(i) Ethylcyclohexane
(ii) 1,2-dimethylcyclopentane
(iii) 3,4-diethyl-2,2-dimethylheptane
(iv) 4- Ethyl-2,2,7-trimethyloctane [8]

(c) Draw Newman projections of the staggered and encliped conformation for 2-methyl pentane
considering the rotation along C3-C4 sigma bond and indicate the most stable conformation of 2-
methylpentane at room temperature [4]
(d) Give the free radical reaction mechanism when methane (CH4) reacts with Chlorine gas (Cl2) in
the presence of light to produce dichloromethane (CH2Cl2) [3]
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TOTAL = [20 MARKS]
QUESTION TWO
…………………………………………………………………………………………………………..
(a) Give one reason and explain why alkenes are generally more reactive than corresponding alkanes
[1]
(b) Give the structures of all possible products in each of the following reactions
(i). 1-butene + HI
(ii). 3-methylcyclohexe + Br2 [3]

(c) Write the structure of the appropriate alkene and specific reagents may be used for synthesis of
each of the following alcohols .
OH
(i). OH (ii)
[10]
(d) Write the mechanism for the acid catalyzed addition of water to propene to produce
2-propanol [6]
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TOTAL = [20 MARKS]
2019-2020 CH 260 TEST 1
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QUESTION THREE
…………………………………………………………………………………………………………
(a) Translate each of the following names into an appropriate structural formula. [4]

(i) 1-Ethyl-3-methylcyclohexane
(ii) 2,3-dimethylbut-2-ene
(iii)2- Methyl-1,5-hexadiene
(iv) Cyclohexa-1,4-diol

(b) Give the IUPAC names for the following compounds

(i). CH3CH= CBrCH3
(ii).CH2 =CHCH2CH2CH= CHCH3 [2]

(c) Give the IUPAC names of the following compounds

(i)
[1]

(ii) [1]

(iii) [1]

(d) Alkenes undergo addition reaction (or bromination) with bromine the reaction which may used to
test for the presence of multiple bonds. Write the reaction mechanism for the bromination of
propene. [5]

(e) After the ozonolysis of an alkene, equal amounts of acetone, (CH3)2 C = O, and formaldehyde,
CH2 = O, and produced. Deduce the structure of the alkene and give its IUPAC name. [2]

(f) Briefly discuss any two laboratory method for the synthesis of alkenes.
[4]
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TOTAL = [20 MARKS]

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QUESTION FOUR
………………………………………………………………………………………………………
(a) By drawing the appropriate structures, predict the products of the following reactions

(i)
[1]

(ii) [1]

(iii) [1]

(iv) [1]

(v) [1]

(vi) [1]

(vii) [1]

(b) Write the mechanisms for the (ii) and (v) above [13]
…………………………………………………………………………………………………………..
TOTAL = [20 MARKS]

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QUESTION FIVE
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(a) Convert the following perspective formulas to Fischer projections. [4]

(b) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound? [3]

(c) The following questions are based on the molecule for each of the molecules shown below.

(i) How many tetrahedral stereocenters does the molecule contain? [1]
(ii) Does the molecule possess any internal planes of symmetry? [1]
(iii)Is the molecule chiral? Give reason [2]
(iv) Is the molecule superposable on its own mirror image? Give reason [2]
(v) Can this molecule be optically active? Give reason [3]
(vi) Is this a meso compound? [2]
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TOTAL = [20 MARKS]

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QUESTION SIX
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(a) You have a sample x which is a mixture of +/- Carvone. The solution was made by dissolving
5.0 g of the sample in methanol to bring the volume of solution to 10.0 mL. Some of the solution
is placed in a 100 cm polarimeter cell and its optical rotation is measured at 25°C using light of
the sodium D line wavelength (589.6 nm). The observed rotation is +24.2°.

(i) What is the specific rotation of this sample? [3]

(ii) An enantiomerically pure sample of the S enantiomer of Carvone has a specific rotation of
+16.5°. What is the % enantiomeric excess of Sample X? [3]
(iii) What percentage of Sample X is the S enantiomer? [3]
(iv) What percentage of the sample X is the R enantiomer? [2]

(b) Draw a three-dimensional structure of each of the compounds named below. Make sure that your
drawings show structures in the given configurations.

(i) (R)-2-bromopentane [3]

(ii) (2R,3S)-3-methyl-2-hexanol [3]

(c) Label each asymmetric carbon in the compound below as R or S.

[3]

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TOTAL = [20 MARKS]

END OF TEST

2019-2020 CH 260 TEST 1

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