WOLAITA SODO UNIVERSITY

COLLEGE OF SCIENCE
DEPARTMENT OF CHEMISTRY
COURSE NAME: Practical organic CHEMISTRY III
Final exam
Course code: chem. 1012 Date: 14/08/2013 E.C
Prepared by: Tesfahun D. Time Allowed: 2:00 hr
Target group: weekend students Total Mark (50%)
Semester: II

NAME __________________________________________________ ID NO ________________SECTION

_______
GENERAL INSTRUCTION
 Make sure that the exam contains five parts and eight pages without the cover page and the periodic
table
 Switch off your mobile phone
 Follow the instruction for each part carefully
 Any kind of cheating and attempt of academic dishonest in the exam room will be accountable
according to the rule of registrar/ F grade
 Put your answer on the space provided clearly and neatly
 Do not turn this page until you told to do so
For instructor use only!!
Part I (5%) Part II (15%) Part III (5%) Part IV (5%) Part V (20%) Total (50%)

Part I: Multiple choices

1. Which substance would test positively with 2,4-DNP but negatively with Tollens’
reagents
A) Propanal B) propan-1-ol C) propanoic acid D) propanone

2. Which of the following flame zones is/are contain the unburned gas
A. the outer /Pale –yellow or C. the middle/ pale blue color/cone
colorless color/ cone D. None of these
B. the inner /dark-blue color/ cone E. All

3. Among the flame zone the coolest cone is

A. The middle cone C. Pale yellow cone
B. The outer cone D. The inner cone

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 4. Give a simple test to differentiate cyclohexane and cyclohexene
A. Br2/H2O D. Both A and C
B. Tollen’s reagent E. Both A and B
C. Bayer’s reagent
5. What is the reagent used to distinguish CH3OH and C (CH3)3OH compounds chemically?
A. Tollen’s reagent C. Ferric chloride reagent
B. Fehling’s reagent D. Jone’s reagent
6. Aldehydes and ketones react with 2,4-DNP to produce
A. Orange color of 2,3-dinitrophenylhydrazones solution
B. Precipitated canary yellow to scarlet color of 2,3-dinitrophenylhydrazines
C. Orange color of 2,3-dinitrophenylhydrazines solution
D. Precipitated canary yellow to scarlet color of 2,3-dinitrophenylhydrazones
7. Which one of the following is false about bimolecular nucleophilic substitution reaction/
having predominate formation of 1-Bromobutane
A. Using polar aprotic solvent and strong and sterically hindered bases
B. The rate depends on both the substrate and nucleophile concentration
C. Can be favor by using unhindered carbon center
D. The reaction accomplished in two step or multi step mechanism
E. The stereochemistry mainly involves Inversion configuration
8. In a method of identification of the given compound in instrument based analysis, one of
the following instruments is used.
A. Mass spectroscopy C. NMR spectroscopy
B. IR Spectroscopy D. All
9. One of the following is not true about aromatic compounds
A. Follow 4n + 2∏ electrons C. They undergo addition reaction
( Huckel’s rule) D. Readily undergo electrophilic
B. They are cyclic compounds substitution reaction
10. All of the following compounds are unsaturated hydrocarbons except which one?
A. 2-Butene B. 3-Heptyne C. 2-Methyl-3, 4 –dibutene D. Cyclopropane
Part II: Give short answers
11. State the reason, why aromatic compounds form sooty when we ignite with matchstick?

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 12. How could you check the purity of your 1-bromoutane product?
13. 1-Bromobutane can be synthesized by nucleophilic substitution reaction as given below;

H2SO4
OH Br
n-butanol NaBr 1-Bromobutane
bp 118°C den 0.810 bp 101.6°C den 1.275
MW 74.12 n 1.399 MW 137.03 n 1.439

A student used 5.0 g of sodium bromide, then 25 ml of a 6.0 M solution of 1-butanol. The
student yielded 8.6 g of product, and was told to assume that the product was pure 1-
bromobutane. Calculate the following:
a) Theoretical yield in grams
b) Percent yield
14. Bromine is used as a color reagent to test for the presence of pi bonds (alkenes &
alkynes) but will also react with phenols (aromatic alcohols). The disappearance of the
red bromine color indicates that a chemical reaction has occurred. However, the organic
compound could be reacting either by addition (alkene or alkyne) or substitution
(phenols). How can you tell the difference?
15. Write down at least four laboratory safety rules.
16. Write the general format of writing laboratory report.(3pts)
17. Write the procedure you follow during the preparation of 1-bromobutane from 1-butanol.
18. Explain why for the confirmation of unsaturation in a compound both the tests namely
test with bromine water and test with Bayer’s reagent should be performed.
19. What is/are the limitation of aldol addition/condensation reaction? And how you could
improve those limitations?
20. When compound A dissolved in chromate it gives positive green colored solution, but
reluctant to change in the presence of silver nitrate or Tollen’s reagent. What is the
functional group of compound A?

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