Sch2108:Organic Chemistry Question Paper
Sch2108:Organic Chemistry
Course:Bachelor Of Science In Public Health
Institution: Meru University Of Science And Technology question papers
Exam Year:2014
1
MERU UNIVERSITY OF SCIENCE AND TECHNOLOGY
P.O. Box 972-60200 – Meru-Kenya.
Tel: 020-2069349, 061-2309217. 064-30320 Cell phone: +254 712524293, +254 789151411
Fax: 064-30321
Website: www.must.ac.ke Email: info@mucst.ac.ke
University Examinations 2012/2013
FIRSTYEAR, SECOND SEMESTER EXAMINATIONS FOR THE DEGREE OF
BACHELOR OF SCIENCE IN PUBLIC HEALTH, BACHELOR OF SCIENCE IN
HORTICULTURE, BACHELOR OF SCIENCE IN FOOD SCIENCE AND NUTRITION
AND BACHELOR OF SCIENCE IN FOOD SCIENCE AND TECHNOLOGY
SCH 2108: ORGANIC CHEMISTRY
DATE: APRIL 2013 TIME: 2 HOURS
INSTRUCTIONS: Answer question one and any other two questions
QUESTION ONE (30 MARKS)
a) Give IUPAC names of the following compounds; (6 Marks)
i) CH2 CHCH CH2
CH3
ii)
iii) H C C C H
O
H H
H H
b) Show and name all the structures of the compound with molecular formulae.
(4 Marks)
i. C4H10
2
ii. C2H6O
c) Give the names of the functional groups represented by the following structures.
(4 Marks)
i) C C OH
O
ii) C C C
O
d) i) Using electronic orbital diagrams, show how sp3 hybrid orbitals are formed in the
carbon atom (c=6). (4 Marks)
ii) Describe the bonding in the formaldehyde molecule, H2CO in terms of atomic
orbital overlap identifying the ?? and ?? bonds. (4 Marks)
e) Complete the following chemical reactions showing all the intermediates where
necessary. (8 Marks)
i) CH3C CH + H2O
H2SO4
HgSO4
ii) CH3CH3+Cl2
iii) CH3CH2OH+CH3COOH
iv) CH3C HCH3
Na2Cr2O
H2SO4
OH
QUESTION TWO (20 MARKS)
a) Assign the E and Z stereochemistry to the following compounds. (6 Marks)
i) C C
H
CH3
C
CH3
CH2
H
3
ii) C C
C
CH
CH3
H3C
H2C
H
Br
H
iii) C C
CH3
H CH2OH
C
O
OH
b) Show how you would prepare the following carboxylic acids through a Grignard
synthesis. (6 Marks)
i. 2,2 – Dimethylpropanoic acid
ii. Hexanoic acid
c) Give an equation to show how you can prepare acetic anhydride, CH3 C O C CH3
O
O
(4 Marks)
d) Benzoic acid C6H5 COH
O
reacts with methanol, CH3OH to form an ester
C6H5 C OCH3
O
, using an acid catalyst (H+), show the reaction mechanism for this
reaction. (4 Marks)
QUESTION THREE (20 MARKS)
a) Give two acceptable names for each of the following compounds. (6 Marks)
i)
Br
Br
4
ii)
Cl
Cl
SO3H
HNO3
H2SO4
b) Benzene reacts with bromine in presence of a Lewis acid as shown
+ Br2
FeBr3
heat
Br
+ HBr
If FeBr3 is generated insitu during the reaction,
i. Write an equation to show how FeBr3 is produced. (2 Marks)
ii. Write a reaction mechanism to show how the bromide ion, Br- is produced.
(2 Marks)
iii. Show the reaction mechanism for the formation of;
Br
(4 Marks)
iv. Identify the arenium ion formed as an intermediate in the process of formation
of the final product. (2 Marks)
c) Show the major products of the following reactions;
i. Nitration of methylbenzene (2 Marks)
CH3
HNO3
H2SO4
ii. Nitration of benzene sulphonic acid (2 Marks)
5
SO3H
HNO3
H2SO4
QUESTION FOUR (20 MARKS)
a) Using relevant examples explain the following;
i. sp2 hybridization (2 Marks)
ii. sp hybridization (2 Marks)
b) Sketch to illustrate the electron density of sp3 hybrid orbitals. (2 Marks)
c) C4H10 is an unsaturated hydrocarbon;
i. Draw a line-bond structure for the given compound and indicate the type of
hybridization on each carbon atom. (3 Marks)
ii. What kind of covalent bonds are observed in alkenes? (2 Marks)
iii. Show and name all the isomers of the compound, C4H10. (3 Marks)
d) Write equations to show how you can prepare CH3CH2COOH from
i. An alcohol
ii. An alkylhalide via a Grignard reagent. (2 Marks)
iii. An acylchloride (2 Marks)
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