BABCOCK UNIVERSITY, ILISHAN REMO

CENTRE FOR FOUNDATION STUDIES

JUPEB SECOND SEMESTER EXAMINATION 2023/2024

COURSE: ORGANIC CHEMISTRY

CODE: CHM 004 TIME: 2HRS

INSTRUCTION: Answer all questions in Section A and three questions in Section B

1. In propyne there are______________ (a) six sigma bonds and two pi bonds (b) seven sigma
bonds and one pi bond (c) six sigma bonds and one pi bond (d) eight sigma bonds

2. When the carbon atom is sp2 hybridized in a compound, it is bonded to ________ (a) 2 other
atoms (b) 4 other atoms (c) 3 other atoms (d) 5 other atoms

3. Compound in which carbons use only sp3 hybrid orbital for bond formation is ____________
(a) CH3 CH2CH3 (b) CH3CH=CH2 (c) CH2=CHCH=CH2 (d) CH3CH=C=CH2

4. An inductive effect refer to the movement of electrons through ________ (a) pi bonds (b) p
orbital (c) non polar (d) sigma bonds

5. Nucleophile have ___________ (a) only bonding electron pairs (b) nonbonding electron pairs
(c) no nonbonding electron pairs (d) a positive charge

6. Which of the following is not a nucleophile? (a) Hydroxide OH- (b) Water H2O (c) Methane
CH4 (d) Chloride Cl-

7. Carbocation are _______ (a) neutral species (b) electrophilic (c) nucleophilic (d) molecules

8. What is the hybridization of the C atom in the methyl cation? (a) C atom is sp 3 hybridized
(b) C atom is not hybridized (c) C atom is sp2 hybridized (d) C atom is sp hybridized

9. To know whether the compound has Nitrogen or not, sodium fusion extract is treated with-
_______

(a) dilute H2SO4, FeSO4 (b) dilute H2SO4, Fe2(SO4)3 (c) FeCl3 (d) dilute HCl, FeCl3
10. 0.78g of an organic compound when heated in presence of CuO in a current of pure oxygen
released 2.64g CO2 and 0.54g H2O. Determine the percentage of carbon and hydrogen in the
compound (a) C (84.7%) , H (15.3%) (b) C (92.3%) , H ( 7.69%) (c) C (88.5%), H (
14.5%) (d) C (90%) , H ( 10%)

11. The IUPAC name of

(a) 3,4-diethylpent-1-en-5-ol (b) 2,3-diethylpent-4-en-1-ol (c) 3-ethenyl-2-ethylpentan-1-ol

(d) 2,3-diethylpent-1-en-5-ol

12. The IUPAC name of (a) 4-chloro-3-methylbut-1-ene

(b) 1-chloro-2-methylbut-3-ene (c) 3-chloromethylbut-1-ene (d) 3-methyl-4-chlorobut-1-ene

13. The IUPAC name of (a) 1,2- dimethylcyclohexene

(b) 1,6-dimethylcyclohexene (c) 2,3-dimethylcyclohexene (d) 1,2-dimethylcyclohex-5-ene

14. The IUPAC name of (a) 2-chloro-3-nitro-4-aldehyde butanol

(b) 4-aldehyde-2-chloro-3-nitro butanol (c) 3-chloro-4-hydroxy-2-nitro butanal (d) 2-chloro- 2-
nitro- 4-hydroxy butanal

15. The IUPAC name of (a) 2,3,3,7,7-pentachloro

octane (b) 2,2,6,6.7-pentachloro octane (c) 3,3,7,7-tetrachloro octane (d) 1,1,5,5,6-pentachloro
octane
16.A tertiary carbocation is more stable than either a secondary or primary carbocation because
(a) it carries three positive charges (b) it has a pyramidal configuration (c) it has a trigonal planar
(d) it possesses three electron –donating substituent group

17. The order of stability of carbocation is (a) primary < secondary < tertiary (b) secondary >
tertiary > primary (c) primary > secondary > tertiary (d) primary > tertiary> secondary

18. The order of stability of carbanion is (a) tertiary > secondary > primary (b) tertiary > primary>
secondary > primary (c) tertiary < secondary< primary (d) secondary > primary> tertiary

19. Free radical ______ (a) contain no electrons (b) contain unpaired electrons (c) contain all
paired electron (d) none of these

20. Homolytic cleavage means a bond ________ (a) breaks to form two radicals (b) breaks to
form ionic species (c) is formed from two radicals (d) is formed from two ions

21. Homoltyic bond cleavage gives (a) cations (b) anions (c) radicals (d) cations and anions

22. Lewis acids (a) donate electrons (b) accept electrons (c) are electron rich (d) are
proton donor

23. Isomers are different compounds having the same (a) physical properties (b) chemical
properties (c) molecular weight (d) solubilities

24. Structural isomers differ in the ________ (a) spatial arrangement of atoms (b) structure i.e
connectivity of atom (c) configuration (d) conformation

25. Stereo isomers differ in the ______ (a) connectivity (b) spatial arrangement of atom or group
around an atom (c) both a and b (d) molecular weight

26. 2-methyl pentane and 3 –methyl pentane are (a) Chain isomers (b) Position isomer (c)
Metamers (d) Functional isomer

27. Diethylamine and methylpropylamine are (a) Metamers (b) Tautomers (c) Functional
isomers (d) Chain isomer

28. Propanal and Propanone are (a) Metamers (b) Tautomers (c) Functional isomers (d)
Position isomer
29. Alkenes show geometrical isomerism due to (a) Asymmetry (b) Rotation around a single
bond (c) Resonance (d) Restricted rotation around a double bond

30. Which of the following compounds exhibit geometrical isomerism (a) 1-Pentene (b) 2-
Pentene (c) 2-Methyl -2-pentene (d) 2-Methyl-2-butene

31. Which of the following compound will show geometrical isomerism? (a) CH2=CHCl2
(b) ClCH=CHBr (c) CH2=CHCl (d) Cl2C=CBr2

32. An optically active compound _________ (a) must contain at least four carbons (b) when in
solution rotate the plane of polarized light (c) must always contain an asymmetric carbon atom
(d) in solution always give a negative reading in polarimeter

33. Optical isomers that are mirror images are called (a) Tautomer (b) Diastereomers (c)
Enantiomers (d) Metamers

34. Optical isomer that are not mirror images are (a) Diastereomers (b) Enantiomers (c)
Metamers (d) Meso compound

35. A meso compound _______ (a) is an achiral molecule which contains chiral carbons (b)
contains a plane of symmetry or a centre of symmetry (c) is optically inactive (d) is characterized
by all of the above

36. The optical purity of isomer is 40%. It is dextrorotatory. The percentage of dextrorotary isomer
is (a) 30% (b) 60% (c) 70% (d) 50%

37. In the chlorination of alkanes the first step in which chlorine free radical are produce is called
________ (a) initiation (b) propagation (c) activation (d) termination

38. An electrophilic addition is _____________(a) an addition to an alkene initiated by a

nucleophilic attack (b) an addition to an alkene initiated by an electrophilic attack (c) a reduction
reaction (d) an oxidation reaction

39. Propene reacts with bromine molecules to form 1,2-dibromopropane. This is an example of
________ (a) Nucleophilic addition (b) Electrophilic addition (c) Nucleophilic substitution
(d) Electrophilic substitution
40. The dehydrohalogenation of 2-bromobutane with alcoholic KOH gives mainly (a) 2-Butene
(b) 2-Butyne (c) 1-Butene (d) Butane

SECTION B ( Answer Three Question Only)

1.a) Define the following terms; (i) Hybridization (ii) Homologous Series (iii) Carbocyclic
Compound (iv) Heterocyclic Compound (v) Tertiary Carbon (vi) Homocyclic Compound

b) (i) Mention 3 characteristic of Homologous Series

(ii) A dry cleaning solvent (M.M=146.99g/mol) that contain C, H, and Cl is suspected to be

a cancer causing agent. When a 0.250g sample was studied by combustion analysis, 0.451g of CO2
and 0.0617g of H2O [Link] the molecular formula [C=12, H=1 Cl=35.5]

c) Mention two purification method for organic compound . Explain one of them

2.a) (i) Mention 3 different types of organic reaction . Explain one of them with suitable explain

(ii) What is the essential difference between a free radical reaction and ionic reaction

b) Explain the following terms with suitable example

(i) Carbocation and Carbanions

(ii) Electrophile and Nucleophile

c) Complete the following reaction ;

(i) CH3CH=CHCH3 + H2 →

(ii) CH3CH=CHCH3 + HBr →

(iii) CH3CH2CH2CH2Cl →
Alcoholic KOH
d) Explain the stability of carbocation using the resonance effect and inductive effect

3. a) (i) Describe the mechanism of SN1 and SN2 reaction

(ii) Mention 3 factor influencing SN2 reaction

(iii) Differentiate between SN2 and SN1. Mention three

b) (i) What is Inductive Effect and Electromeric Effect

 (ii) Mention 3 differences between inductive effect and electromeric effect

(iii) Describe homolytic and heterolytic fission of a covalent bond. How carbocation, carbanion
and free radical are obtained?

4. a) (i) Define the following term (i) Structural Isomerism (ii) Optical Isomerism (iii) Racemic
Mixture (iv) Stereoisomerism (v) Chiral Carbon (vi) Chain Isomerism

b). Draw the structure for each of the following (i) (Z)- 1,3,5-Tribromo-2-pentene

(ii) (Z)- 3- Methyl-2-heptene (iii) (E) -3- Methyl-2-pentene

c) Your lab partner tells you that a sample of (+) -2-butanol has an apparent specific rotation of
+ 13.8 and is known to be a mixture enantiomer with optical purity of 94%. How much of each
enantiomer is in the mixture? What is the specific rotation of enantiomerically pure (+) -2-butanol

d) (i) Define Plane Polarized Light (ii) What is optically active substance?

(iii) What is plane of symmetry?. Mention two example of objects with plane of symmetry

5 a) The following two compounds belong to a homologous series. Fill the structure of the missing
members between these two compounds

CH3CH2Cl_____________________ CH3 (CH2)5 CH2Cl

b) Write a structure for each of the following compounds. Explain why the given name is wrong
and give a correct name in each case

(i) 1-Methylpentane (ii) 2-Ethylbutane (iii) 2,3-Dichloropropane

(iv) 3-bromo-2-methylpropane

c) Write a structural formula of the following compound

(i) 2-chloro-5-methyl hexanal (ii) 3-methyl-1-butanol (iii) 1,4-pentadiene

(iv) 4-Hydro-2-methylpentanoic acid

d) What do you understand by the term Principal Functional Group?

ii) When the following groups are present in a molecule what will be its principal or class name

(i) –OH, -COOH, -NO2 (ii) –Br, -CH3, -CHO (iii) –NH2 , -OCOR, -CO-
 BABCOCK UNIVERSITY

CENTRE FOR FOUDATION STUDIES

JUPEB SECOND SEMESTER EXAMINATION

2023/2024 SESSION

CHEMISTRY PRACTICAL TIME: 2hrs

1. A is a solution of HCl . B is a solution of Na2CO3 containing 5.3g in 500cm3 .Put A into the burette
and titrate it against 25cm3 portion of B using methyl orange as indicator. Repeat the titration to
obtain consistent titre value. Tabulate your results

(i)Write the equation for the reaction

(ii) Calculate the average volume of A used

(iii) Calculate the mole of A and B used in 25cm3 and 1000cm3 solution

(iv) Calculate the concentration of B in mol/dm3

(v) Calculate the concentration of A in mol/dm3

(vi) Calculate the concentration of A in g/dm3