CHEMISTRY: Organic chemistry : Some basic principles & techniques

1. The correct order of electronegativity of carbon in ethane, thene and ethyne is

(a) Ethane < Ethene < ethyne b) ethyne < ethene < ethane
c) ethene < ethyne < ethane d) ethene < ethane < ethyne
2. Electronegativity of carbon atoms depends upon their state of hybridisation. In which of the following compounds,
the carbon marked with asterisk is most electronegative ?
a) CH3 – CH2-* CH2- CH3 b) CH3 - * CH = CH – CH3
c) CH3 – CH2 – C ≡* CH d) CH3 – CH2 –CH = * CH2
3. Chose the correct bond line formula for
H3C CH3
H C-C H
H3C CH3
a) b) c) d)
4. In cyclic compounds, the bond-line formula for chlorocyclohexane is represented by which of the following
representations. ? Cl Cl Cl
Cl
a) b) c) d)
5. The correct way (s) of representing 2-bromobutane is/are
a) CH3CHBrCH2CH3 b) H3C CH2 c) d) All of the above
CH CH3
Br Br
6. The IUPAC name for
a) 1-hydroxypentane -1.4 dione
b) 1,4 – dioxopentanol
c) 1-carboxybutan -3- one d) 4-oxopentanoic acid

7. In which of the following, functional group isomerism is not possible ?

a) Alcohols b) Aldehydes c) Alkyl halides d) Cyanides
8. The number of structural isomers possible for the molecular formula = C 3H9N is
a) 4 b) 5 c) 2 d) 3
9. Study the structures given below carefully and choose the type of isomerism they represent.

a)chain isomerism b) position isomerism c) Functional isomerism d) metamerism

10. The IUPAC name of iso-octane is
a) 2,2 – dimethylpentane b) 2,3 – dimethylpentane
c) 2, 3, 3 – trimethylpentane d) 2,2,4 – trimethylpentane.
11. Write the correct IUPAC name of the following.

a) 1- chloro – 2, 4- dinitrobenzene b) 6- choloro -1 , 3- dinitrobenzene

c) 1- chloro-4, 6 – dinitrobenzene d) 2- choloro-1, 5- dinitrobenzene
12. What is the correct order of decreasing stability of the following cations ?
a) II > I > III
b) II > III > I
c) III > I > II
d) I > II > III
13. Which of the following compounds will exhibit geometrical isomerism ?
a) 1-phenyl – 2 butene b) 3-phenyl -1- butene
c) 2-phenyl 1-butene d) 1 , 1 – dipheny 1- 1 – butene
14. In which of the following compounds the carbon marked with asterisk is expected to have greatest positive charge
a) *CH3 – CH2 – Cl b) *CH3 – CH2 – Mg+Cl- c) *CH3 – CH2 – Br d) *CH3 – CH2-CH3
15. Choose the correct order of stability of carbocation using the concept of hyperconjugation.

a) I < II < III < IV b) IV < III < II < I c) III < IV < II < I d)None of these
16. The difference in energy between the actual structure and lowest energy canonical form is called
a) Resonance energy b) Localisation energy c) Both (a) and (b) d) All of these
17. Consider the following compounds.

Which of the following statements is/are true regarding I and II ?

a) I shows + R – effect whereas II shows -R – effect b) I shows – R – effect, whereas II shows + R – effect
c) Both I and II show + R – effect c) Both I and II show – R- effect
18. How many σ and π bonds are present in HC ≡ C – CH = CH –CH3 ?
a) 9σ , 4 π b) 10σ , 3 π c) 6σ , 6 π d) 5σ , 5 π
19. Which of the following represents the given sequence of hybridisation of carbon atoms from left to right sp 2, sp2, sp,
sp ?
a) H2C = CH – C ≡ CH b) HC = C-CH = CH2 c) H3C-CH=CH –CH3 d) H2C = CH- CH= CH2
20. The hybridisation of carbons of C-C single bond of HC ≡C – CH = CH2 is
a) sp3 – sp3 b) sp –sp2 c) sp3-sp d) sp2-sp3
21. What are the hybridization and shapes of the following molecules ?
i) CH3F ii) HC ≡ N
2 3
a) (i) sp , Trigonal planar ; ii) sp , tetrahedral b) (i) sp3, tetrahedral ; (ii) sp, linear
c) (i) sp, liner ; (ii) sp3 , trigonal planar d) (i) sp2, trigonal planar (ii) sp2 trigonal planar
22. IUPAC names of the given structures are

(i) (ii)

a) (i) hexane, (ii) 3- methylbutane b) (i) isopentane, (ii) 2,2 – dimethylbutane

c) (i) 3 – ethylbutane, (ii) isopentante d)(i) 3 –methylpentane, (ii) 2- methylbutane.
23. Correct name for the given compound, CH 3 –CH2 –CH - CH2 – CH – CH2 – CH3 is
CH2CH3 CH3
a) 3- ethyl – 5 – methylheptane b) 5- ethyl -3- methylheptane
c) 1, 1 – diethyl -3- methylpentane d) 3- methyl – 5,5- dietpthylpentane.
24. IUPAC name of (CH3)3 C – CH = CH2 is
a) 2, 2- dimethylbut – 3- ene b) 2, 2- dimethylpent -4- ene
c) 3, 3 – dimethylbut -1- ene d) hex -1- ene
25. Which of the following represents 3- methylpenta – 1, 3 – diene ?
a) CH2 = CH(CH2)2 CH3 b) CH2 = CHCH(CH3)CH2CH3 c) CH3CH = C(CH3)CH =CH2 d) CH3CH=C(CH3)2
26. The correct representation of 4-hydroxy -2- methylpent – 2- en- 1 –al is
a) CH3 – CH – CH = C – CHO b) CH3 – CH – CH = C – CHO
OH CH3 CH3 OH
CH3
c) CH3 – C – CH = C – CHO d) CH3 – CH – CH2 – CH - CHO
OH CH3 OH CH3
27. Which of the following IUPAC name is not correctly matched ?
Cl
a) - Cyclopentane b) - Chlorocyclohexane
NO2
c) 1, 1 – dimethylcyclohexane d) - 3 – Nitrocyclohexane

28. The correct IUPAC name of the following compound is

a) 2 – ethyl - 1 – chlorocylohexanol Cl
b) 4 – Chloro – 5 ethylcycloxannol
c) 4 –hydroxy – 2- ethyl – 1 – clorocyclohxane H2C2 OH
d) 4 – Chloro – 3 ethycylcyclohexanol
29. The IUPAC name of the compound shown below is Cl
a) 2 – bromo – 6 – chlorocyclohex – 1 – ene
b) 6 – bromo – 2 – chlorocylohexen Br
c) 3 – bromo – 1 – chlorocyclohexene d) 1 – bromo – 3 – chlorocyclohexene
30. What is the minimum number of carbon atoms of an alkane must have to form an isomer ?
a) 4 b) 3 c) 2 d) 1
31. Heterolysis of a carbon –chlorine bond produces
a) Two free radicals b) two carbocations c) one cation and one anion d) two carbanions
32. Inductive effect involves
a) displacement of σ - electrons resulting in polarisation
b) displacement of π - electrons resulting in polarisation
c) displacement of σ - electrons
d) delocalisation of π – electrons.
33. Which of the following alcohols on dehydration gives most stable carbocation ?
CH3
a) CH3 – CH – CH2OH b) CH3 – C – OH c) CH3 – CH2 – CH2 – CH2OH d) CH3 – CH – CH2CH3
CH3 OH
34. Assertion : Rotation about C =C is restricted
Reason : Electron charge cloud of the π bond is located above and below the plane of bonding atoms.
a) if both assertion and reason are true and reason is the correct explanation of assertion
b) if both assertion and reason are true but reason is not the correct explanation of assertion
c) if assertion is true but reason is false
d) if both assertion and reason are false
35. Assertion : Alkanes containing more than three carbon atoms exhibit chain isomerism.
Reason : In an alkane, all Carbon atoms are sp 3 hybridised.
a) if both assertion and reason are true and reason is the correct explanation of assertion
b) if both assertion and reason are true but reason is not the correct explanation of assertion
c) if assertion is true but reason is false
d) if both assertion and reason are false
36. Assertion : The order of stability of carbocations is 3° > 2° > 1° .
Reason : Carbon atom in corbocation is in sp3 state of hybridisation.
a) if both assertion and reason are true and reason is the correct explanation of assertion
b) if both assertion and reason are true but reason is not the correct explanation of assertion
c) if assertion is true but reason is false
d) if both assertion and reason are false
37. Which of the statements is not correct regarding sp hybridisation of carbon ?
a) it is shown by compounds with C≡C bond b) it leads to the formation of too hybridised and two
unhybridised orbitals of carbon
c) it results in tetrahedral geometry d) the bond angle in compounds containing sp hybrid orbitals is 180 °
38. The hybridisation of carbon atoms in C – C single bond of HC ≡ C – CH=CH-CH2 – CH3
a) sp3, sp3 b) sp2 sp3 c) sp, sp2 d) sp3 sp
39. What is the IUPAC name of the compound :
CH2 – CH2 – COOH
OH
a) 3 – hydroxypropanoic acid b)2 – hydroxy –1 – amino – propanoic acid
c) 2 – amino – 3 – hydroxypropanoic acid d)1 – amino – 2 – hydroxypropanoic acid
40. Which of the following species has electron releasing (or + I inductive ) effect ?
a) – NO2 b) –COOH c) (CH3)2CH- d) C6H5-
41. CnH2n+2 is the general formula of
a) alkenes b) alkanes c) arenes c) Both alkenes and cycloalkanes
42. The IUPAC name of the following compound is : CH –CH 2 – CH3

a) 2- Cyclohexyl butane b) 1 – Phenylpropane c) 3- Cyclohexyl butane d) 3 – Phenyl butane

43. The first organic compound synthesised in the laboratory by:
a) faraday b) Joul c) F. Wohler d) None of these
44. Which of the following compounds, the carbon marked with asterisk is least electronegative ?
b) CH3 – CH2-* CH2- CH3 b) CH3 - * CH = CH – CH3
c) CH3 – CH2 – C ≡* CH d) CH3 – CH2 –CH = * CH2
45. Correct IUPAC name for H3C –CH−¿CH-CH3 is
C2H5 C2H5
a) 2-ethyl-3- methyplentane (b) 3, 4- dimethylhexane
c) 2-sec-butylbutane d) 2, 3 – dimethylbutane