(

a
u

Organic Chemistry-
Some Basic Principles
& Techniques
----······· 1 ·············· =·· ·· ·········· · ····· ···· ····a 4. The lUPAC name for the following compound is :
:' TOPI{ ' Oassification and Nomenclature [April 12, 2019 (II)]
\ of OJganic Compounds
~-------- ---- -- -------------------------------------
1. The IUPAC name of the following compound is:
!Sep. 06, 2020 (II))

~ N H,

0Ny 2
CHO
CH 2
(a) 3-methyl-4-(3-methylprop-l-enyl)-l-heptyne
(b) 3,5-0imethyl-4-propylhept-6-en-l-yne
(a) 2-nitro-4-hydroxymethyl-5-amino benzaldehyde (c) 3-methyl-4-( l-methylprop-2-ynyl)-l-heptene
(b) 3-amino4-h}'droxymethyl-5-nitrobenzaldehyde (d) 3,5-0imethyl-4-propylhept-1-en-6-yne
(c) 5-amino4-hydroxymethyl-2-nitrobenzaldehyde s. The correct IUPAC name of the following compound is:
(d) 4-amino-2-fonnyl-5-hydroxymethyl nitrobenzene [April 9, 2019 (I)]
2. The IUPAC name of the following compound is :
[Sep. 04, 2020 (I)]

JS)-OH
~Cl
CH 3
(a) 5-chloro-4-methyl- l-nitrobenzene
(b) 2-chloro- l-methyl-4-nitrobenzene
(c) 3-chloro-4-methyl-l-nitrobenzene
Br (d) 2-methyl-5-nitro-1-chlorobenzene
(a) 5-Bromo-3-methylcyclopentanoic acid 6. The IUPAC name of the following compound is :
CH3 OH
(b) 4-Bromo-2-methylcyclopentane carboxylic acid
I I
(c) 3-Bromo-5-methylcyclopentanoic acid H3C- CH - CH- CH 2 -COOH
(d) 3-Bromo-5-methylcyclopentane carboxylic acid [April 8, 2019 (I)]
3. The IUPAC name for the following compound is : (a) 4, 4-Dimethyl-3-hydroxybutanoic acid
[Sep. 02, 2020 (I)] (b) 2-Methyl-3-hydroxypentan-5-oic acid
CHO
(c) 3-H}'droxy-4-methylpentanoic acid
~ ~ /CH 3
H C/
3
'-.?' y 7.
(d) 4-Methyl-3-hydroxypentanoic acid
What is the IUPAC name of the following compound?
COOH CH3 CH3
(a) 2, 5-dimethyl-5-carboxy-hex-3-enal
(b)
(c)
(d)
2, 5-dimethyl-6-carboxy-hex-3-enal
2, 5-0imethyl-6-oxo-hex-3-enoic acid
6-formyl-2-methyl-hex-3-enoic acid
H>=x:, CH3
!Jan. 10, 2019 (II))
 (a) 3-Bromo-l, 2-dimethylbut-1-ene 14. The IUP AC name of the compound
(b) 3-Bromo-3-methyl-l, 2-dimethylprop-1-ene
(c) 2-Bromo-3-methylpent-3-ene
/0...,
H2C - CH - CH 3 is (Online May 7, 2012)
(d) 4-Bromo-3-methylpent-2-ene (a) I, 2-propoxide (b) propylene oxide
8. The IUPAC name of the following compound is : (c) 1,2-oxopropane (d) 1,2-epoxypropane
15. The IUP AC name of the following compound is

IOnline April 15, 2018(1)) CH 3 )c =c,/H

H C = C - CH 2CH 3
(a) 3-ethyl-4-methylhex-4-ene IOnline May 19, 2012)
(b) 4, 4-diethyl-3-methylbut-2-ene (a) (E)-2-hepten-4-yne (b) (Z)-5-hepten-3-yne
(c) 4-methyl-3-ethylhex-4-ene (c) (E)-5-hepten-3-yne (d) (Z)-2-hepten-4-yne
(d) 4-ethyl-3-methylhex-2-ene 16. Dipole moment is shown by (Online May 26, 2012)
9. The IUPAC name of the following compound is : (a) I, 2-dichlorobenzene
IOnline April 8, 2017) (b) trans-2, 3-dichloro-2-butene
(c) I, 4-chlorobenzene

(r'
(a) I, l-dimethyl- 2-ethylcyclohexane
(d)trans-1,2-dinitroethene
17. The IUPAC nameofneopentane is
(a) 2, 2-dimethylpropane (b) 2-methylpropane
12009)

(b) 2-ethyl- l, 1-dimethylcyclohexane (c) 2, 2-dimethylbutane (d) 2- methylbutane

18. The correct decreasing order of priority for the functional
(c) l-ethyl- 2,2-dimethylcyclohexane
groups of organic compounds in the IUPAC system of
(d) 2, 2-dimethyl- 1-ethylcyclohexane nomenclature is (2008)
10. The hydrocarbon with seven carbon atoms containing a (a) - COOH, - SO3H, - CONtti, - CHO
neopentyl and a vinyl group is: (Online April 9, 2016) (b) - SOll, - COOH,- CON~, - CHO
(a) 2, 2-dimethyl-4- pentene (c) - CHO, - COOH, - SO3H, - CON~
(b) 4, 4--dimethyl pentene (d) - CON~. - CHO, - SO3H, - COOH
(c) isopropyl- 2- butene
(d) 2, 2-dimethyl- 3- pentene
19. ThelUPACnameof~ is
11. In allene (C3H4 ), the t}Pe(s) ofhybridization of the carbon
atoms is (are): IOnllne April 11, 2014)
(a) 3-ethyl-4,4-dimethylheptane (2007)
(a) sp and sp3 (b) sp2 and sp
(b) I, 1-diethyl-2,2-dimethylpentane
(c) only sp2 (d) sp 2 and sp3
12. The correct IUPAC name of the following compound is: (c) 4, 4-dimethyl-5,5-diethylpentane
IOnline April 19, 20141 (d) 5, 5-diethyl-4,4-dimethylpentane.
20. The IUPAC name of the compound shown below is:
Cl

(a) 4- methyl - 3 - ethylhexane

68,
(a) 3-bromo-1-chlorocyclohexene
(b) 1-bromo-3-chlorocyclohexene
12006)
(b) 3- ethyl -4- methylhexane
(c) 3,4-ethylmethylhexane (c) 2-bromo-6-chlorocyclohex-1-ene
(d) 4- ethyl-3 - methylhexane (d) 6-bromo-2-chlorocyclohexene
13. Which of the following cannot be represented by 21. The IUPAC name of the compound is 12004)
resonance structures? (Online May 7, 2012)
(a) Dimethyl ether (b) Nitrate anion
(c) Carboxylate anion (d) Toluene
 (a) 3, 3-dimethyl - 1- cyclohexanol Geometrical isomerism is not possible at site (s) :
(b) I, 1-dimethyl-3-hydroxy cyclohexane (a) m (b) I
(c) 3, 3-dimethyl-1-hydroxycyclohexane (c) I and 111 (d) lU and IV
(d) I, l-dimethyl-3-cyclohexanol 29. The absolute configuration of
22. Which one of the following does not have sp2 hybridised

23.
carbon?
(a) Acetonitrile
(c) Acetone
(b) Acetic acid
(d) Acetamide
120041

The general formula CnH1n02 could be for open chain

(a) carboxylic acids
(c) dialdehydes
(b) diols
(d) diketones
120031
:1~~
CH 3
is: 12016)
24. The IUPAC name ofCH3COCH(CH3)2 is 120031
(a) (2S,3S) (b) (2R,3R) (c) (2R,3S) (d) (2S,3R)
(a) 2-methyl-3-butanone
30. Which of the following compounds will exhibit geometrical
(b) 4-methylisopropyl ketone
(c) 3-methyl-2-butanone isomerism? 12015)
(d) lsopropylmethyl ketone (a) 2 - Phenyl - I - butene
25. Which of the following compounds has wrong IUPAC (b) 1, I - Diphenyl - I -propene
name? 12002) (c) 1 - Phenyl - 2 - butene
(a) CHr CH2-CH2 -COO-CH2CH 3 ➔ ethyl butanoate (d) 3- Phenyl -1 - butene
(b) CH 3 - CH - CH 2 - CHO ➔ 3-methyl-butanal 31. The optically inactive compound from the fol lowing is :
I !Online April 10, 20151
CH 3 (a) 2 - chloropropanal
(c) CH 3 - CH - CH - CH3 ➔ 2-methyl-3-butanol (b) 2 - chlorobutane
I I (c) 2 - chloropentane
OH CH 3 (d) 2 - chloro - 2- methylbutane
32. The number of structural isomers for C6H14 is :
0
I !Online April 11, 20151
(d) CH3 - CH - C - CH2 - CH3 ➔ 2-methyl-3-pentanone (a) 4 (b) 3 (c) 6 (d) 5
I 33. Which of the following pairs ofcompounds are positional
CH3
isomers ? !Online April 11, 2015)
26. In which of the following species is the underlined carbon
~)CH 3 - CH 2 - CH 2 - C- CH 3
having sp3 hybridisation? 120021 II
(a) CH3 ~00H (b) CH3 ~Hi OH 0

(c) CH3 ~0C~ (d) Ctti =~H-CH3 and CHr CH 2 - C- CH 2 - CH 3

II
,,•········ 2 ·····················-··-···············--·- 0
( TOPIC Isomerism In Organic
-._ Compounds (b)CH3 - CH2 - CH2 - CH2 - CHO
'-······· ·······································-··· 0
27. Which ofthe following compounds will show the maximum II
and CH 3 - CH 2 -CH 2 - C- CH 3
'enol' content? [April 8, 2019 (m]
(a) ~COC8zCOOC2H5 (b) CJ\COC8zCOCJ\
(c) C}\COC}\ (d) CJ\COC8zCON8z
28. In the following structure, the double bonds are marked as
I, n, mand IV !Online April 9, 2017) and CH 3 - CH-CH2 - CHO
I
CH3

(d) CH 3 - CH2 - C-CH2 - CH 3

II
0

CH\3
and /CH - CH 2-CHO
CH 3
34. Which one of the following acids does not exhibit optical 43. Which one of the following conformations ofcyclohexane
isomerism? !Online April 12, 20141 is chiral? 12007)
(a) Lactic acid (b) Tartaric acid (a) Boat (b) Twist boat (c) Rigid (d) Oiair
(c) Maleic acid (d) a-aminoacids 44. Which of the following molecules is expected to rotate the
plane of plane-polarised light? 12007)
35. Arrange in the correct order of stability (decreasing order)
for the following molecules: !Online April 22, 2013) CHO
Me

H
(Il)µM, (b) HO+H
(I) CHO2H
Me H
H (c)~

SH
Me
H2N ~ N H2
(III)
(d) H l l ~ I I H
Me
Ph Ph
(a) (ij>(ll)>(lll)>(IV) (b) (IV)> (Ill) > (II) :::: (I)
45. Increasing order of stability among the three main
(c)(I)> (II) == (Ill)> (IV) (d) (III)> (I) :::: (II)> (IV) conformatioos (i.e. Eclipse,Anti, Gauche) of2-fluoroethanol
36. How many cyclic structures are possible for C4 H6? is 12006)
[Online May 7, 2012) (a) Eclipse, Anti, Gauche (b) Anti, Gauche, Eclipse
(a) 3 (b) 5 (c) 6 (d) 4 (c) Eclipse, Gauche, Anti (d) Gauche, Eclipse, Anti
37. Maleic acid and furnaric acids are IOnllne May 26, 2012) 46. Which types ofisomerism is shown by 2, 3-dichlorobutane?
(a) chain isomers (b) functional isomers 12005)
(c) tautomers (d) geometrical isomers (a) Structural (b) Geometric
38. The change in the optical rotation of freshly prepared (c) Optical (d) Diastereo
solution of glucose is known as: [2011 RS) 47. Which of the following will have a mesoisomer also?
(a) racemisation (b) specific rotation (a) 2, 3- Dichloropentane I2004)
(c) mutarotation (d) tautomerism (b) 2, 3-Dichlorobutane
39. Out of the following, the alkene that exhibits optical (c) 2-Chlorobutane
isomerism is 12010) (d) 2-H)droxypropanoic acid
(a) 3-methyl-2-pentene (b) 4-methyl-1-pentene 48. Amongst the following compounds, the optically active
(c) 3-methyl-1-pentene (d) 2-methyl-2-pentene alkane having lowest molecular mass is 12004)
40. The alkene that exhibits geometrical isomerism is: 12009) H
(a) 2- methyl propene (b) 2-butene I
(a) CHr C-<J
(c) 2- methyl -2-butene (d) propene I
C2Hs
41. The number ofstereoisomers possible for a compound of
the molecular formula CH3
CH3 - CH= CH - CH(OH) - Me is: I
12009) (b) CH 3 -CH 2 -CH-CH 3
(a) 2 (b) 4 (c) 6 (d) 3
(tjCH 3 -CH2-CH2-CH3
42. The absolute configuration of 12008)
(d) CH 3 -CH 2 -C = CH
49. Which of the following compounds is not chiral?
(a) l-chloro-2-methyl pentane I2004)
(b) 2-chloropentane
(a) S, S (b) R, R (c) R, S (d) S,R (c) 1-chloropentane
(d) 3-chloro-2-methyl pentane
SO. Among the following four structures I to IV, 120031 O 0
CH3 0 CH3
I II I
C2Hs - CH - C3H7 , CH 3 -C - CH-C 2H 5, (d) M.jx~OMe
( I)
( II )
O~OMe
H 57. Glycerol is separated in soap industries by:
I
H - C$ [Sep. 03, 2020 (I)]
I (a) Fractional distillation
H '
(111 ) (IV ) (b) Differential extraction
it is true that (c) Stearn distillation
(a) only I and II are chiral compounds (d) Distillation under reduced pressure
(b) only Ill is a chiral compound
58. The increasing order of basicity for the following
intermediates is (from weak to strong)[Jan. 09, 2020 (I)]
(c) only II and IV are chiral compounds
(d) all four are chiral compounds CH 3
SI. A similarity between optical and geometrical isomerism is I
that 120021 ll3C-ye
(a) each forms equal number of isomers for a given CH
compound (i) 3 (ii)
(b) if in a compound one is present then so is the other e e e
HC~C CH 3 CN
(c) both are included in stereoisomerism
(d) they have no similarity (iii) (iv) (v)
52. Which of the following does not show geometrical (a) (iii) < (i) < (ii) < (iv) < (v)
isomerism? 120021
(b) (v) < (i) < (iv) < (ii)< (iii)
(a) 1,2-dichlor~ 1-pentene (b) l ,3-dichlor~2-pentene
(c) (v) < (iii)<(ii) < (iv) < (i)
(c) I , 1-dichlor~ 1-pentene (d) l,4-dichlor~2-pentene
SJ. Racemic mixture is formed by mixing two 120021 (d) (iii) < (iv) < (ii) < (i) < (v)
(a) isomeric compounds 59. A flask contains a mixture of isohexane and 3-
(b) chi.rat compounds methylpentane. One of the liquids boils at 63 °C while the
(c) meso compounds other boils at 60 °C. What is the best way to separate the
(d) enantiomers with chiral carbon two liquids and which one will be distilled out first?
[Jan. 08, 2020 (I)]
54. Following types of compounds (as I, II) 120021
(a) fractional distillation, isohexane
CH3CH = CHCH 3 CH 3CHOH (b) simple distillation, 3-methylpentane
I (c) simple distillation, isohexane
CH 2CH 3 (d) fractional distillation, 3-methylpentane
(I) (II)
60. The correct order of stability for the following alkoxides
are studied in terms of isomerism in:
is:
(a) chain isomerism (b) position isomerism
o-
(c) con formers (d) stereoisomerism
y N02
(A) (C)

[Jan. fY1, 2020 (II)]

(a) (B) > (A) > (C) (b) (C) > (B) > (A)
SS. In an estimation of bromine by Cari us method, 1.6 g of an (c) (C) > (A) > (B) (d) (B) > (C) > (A)
organic compound gave 1.88 g of AgBr. The mass
61. The increasing order of nucleophilicity of the following
percentage of bromine in the compound is _ _
(Atomic mass, Ag = 108, Br = 80g mol- 1) nucleophiles is: [April 10, 2019 (m]
INV, Sep. 06, 2020 (1)1 (i) CH 3C0 2 (ii) Hp
56. Which one of the following compounds possesses the
most acidic hydrogen? !Sep. 03, 2020 (1)1 (iii) CH 3S03 (iv) OH·
N = CxC = N (a) (i) < (iv) < (iii) < (ii) (b) (ii)<(iii) < (iv) < (i)
(a) H H (b) H 3C - C=C - H (c) (iv)<(i)<(iii)<(ii) (d) (ii)<(iii)<(i)<(iv)
62. The increasing order of basicity of the following 68. A mixture containing the following four compounds is
compounds is (2018) extracted with 1M HCI. The compound that goes to
(t) ~ N H 2 (ii) ~ N H aqueous layer is: (Online April 8, 2017)

(iii)
~NH
NH2
l £
(iv) ~ NHCH3 (I)v
r°Ys" QQo-~ H

~dl
(a) (i)<(ii)<(iii)<(iv) (b) (ii)< (i) <(iii)< (iv) 0

63.
(c) (ii)<(i)<(iv)<(iii) (d) (iv)< (ii)< (i) < (iii)
The most polar compound among the following is :
(111)0-0......
(Online April 16, 2018)
(a) (I) (b) (II) (c) (UI) (d) (IV)

(a)()y
F

(b)~
A 69. The increasing order of the reactivity of the following
halides for the SN I reaction is (20171
CH3CHCH2CH3 CH3CH2CH2Cl
F I
F
Cl

(d)~
A (I) (II)

p-H3CO-C6 H4-CttiCl
F (Ill)
64. On the treatment of the following compound with a strong
acid, the most susceptible site for bond cleavage is: (a) (lll) < (II) < (l) (b) (0) <(I)< (lll)

m o.).___ (Online AprU IS, 2018(Il)(

70.
(c) (l)<(ill)<(ll)

stabilized?
(d) (Il) < (Ill) < (I)
Which of the following molecules is least resonance
(2017]

(b)o
2 5

6S.
(a) 02 - C3
(c) C4 - 05
(b) 05 - C6
(d) Cl - 02
Two compounds I and II are eluted by column chromato-
graphy(adsorption off> 11). Which one of the following is
(•JO 9.
a correct statement? (Online April 15, 2018 (II)(
(a) II moves slower and has higher R; value than I
(b) II moves faster and has higher R,- value than I <c>OI (d) ~
~N 0~
(c) I moves faster and has higher Rr value than II
(d) I moves slower and has higher R,-value than II 71. The distillation technique most suited for separating
66. Which of the following statements is not true about glycerol from pent-I-ye in the soap industry is: (20161
partition chromatography? (Online April 8, 2017] (a) Steam distillation.
(a) Mobile phase can be a gas (b) Distillation under reduced pressure.
(b) Stationary phase is a finely divided solid adsorbent (c) Simple distillation
(c) Separation depends upon equilibration of solute (d) Fractional distillation
between a mobile and a stationary phase 72. For which of the following molecule significant µ :t:- O?
(d) Paper chromatography is an example of partition (20141
Cl CN OH SH

¢ (fu)¢ (iv)¢
chromatography
67. The increasing order of the boiling points for the following
compounds is: (Online April 9, 20171 (i) (ill
C2"50H C2"5O C2"5CH3 C2"50CH3
(I) (II) (Ill) (IV) OH SH
Cl
(a) (Ill) < (IV) < (0) < (I) (b) (IV)< (III)< (I) < (Il)
(a) Only(i) (b) (i)and(ii)
(c) (II) < (UI) < (IV) < (I) (d) (Ill) < (II) < (I) < (IV)
(c) Only(iii) (d) (iii) and (iv)
73. In which of the following pairs A is more stable than B? 78. In nucleophilic substitution reaction, order of halogens as
!Online April 9, 20141 incoming (attacking) nucle~hile is:
A B 1- > Br - >Cl-

<•>O.
•
o· The order of halogens as departing nucleophile should
be :
(a) Br>J - >Cl-
(Online April 25, 2013]
(b) 1- > Br> c1-

(b)o·. 0• 79.
(c) Cl- >Br> 1- (d) c1- > 1- > Br
In the below mentioned compounds the decreasing order
• of reactivity towards electrophilic substitution is

(c) D: 0 ~
(Online May 12, 2012)

(d) Ph 3C-, (CH3) 3 c• (i)y (ii) ~

y~
74. A solution of( - ) - l - chloro - 1- phenylethane in toluene OCH3 CH 3
racemises slowly in the presence of a small amount of
SbC1 5, due to the formation of:
(a) carbanion (b) carbene
(2013) (iv)Q
(c) carbocation (d) free radical CF3
75. The order of stability ofthe following carbocations: 12013) (a) (iv)> (i) >(ii)> (iii) (b) (ii)> (iii)> (i) > (iv)
E9 (c) (iii)> (i)> (iv)> (ii) (d) (i)>(ii)>(iii)>(iv)
2
80. The correct order of increasing basicity of the given
CH 2 =CH-~H 2 ; CH 3 -CH 2 -~H 2 ;6CHl is: conjugate bases (R = CH 3) is
(a) RCOO < HC = C < R < NH 2
(20101

I II ~
Ill
(a) m> 0 > I (b) O>IO>I (b) R < HC =C < RCOO < NH 2
(c)l>O>ID (d) m> I> n (c) RCOO<NH 2 <HC=C<il
76. Which one of the following is most stable?
(Online April 9, 2013) (d) RCOO < HC = C< NH2 < R

(a)~ (b)o
+ 81. Arrange the carbanions,
-
(CH 3)]C ,C Cl3,(CH3)iCH ,C6HsCH2
-
(2009)

(c)o
UPh order of their decreasing stability is
+
(YH (a) (CH 3 )iCH > CCl 3 > C6 H5 CH 2 > (CH 3)JC
(d)y (b) CCl 3 > C6 H5 CH 2 > (CH 3 )iCH > (CH 3 )]C

Ph (c) (CH 3 )JC > (CH 3 )iCH > C6 H5 CH 2 > CCl 3

77. Given (Online April 25, 2013)
(d) C6 H5 CH 2 > CCl3 > (CH 3 )JC > (CH 3 )iCH

or560
82. The electrophile, Ee attacks the benzene ring to generate
the intermediate a-complex. Of the following, which a-
complex is lowest energy? (2008)
(A) (8) (C) (D)
In the above compounds correct order of reactivity in
electrophilic substitution reactions will be :
00B>A>C>D (b) D>C>B>A
(c) A> B> C> D (d) B>C> A> D
 0
(C) CN - (D) H 3C ~ ~ - o- is
~ II
0
(a) (C) > (B) >(A)> (D) (b) (B) > (C) >(A)> (D)
83. Presence ofa nitro group in a benzene ring 12007) (c) (D) > (C) > (B) > (A) (d) (A)>(B)>(C)>(D)
(a) deactivates the ring towards electrophilic substitution 89. The reaction 1200S, 2004)
(b) activates the ring towards electrophilic substitution
(c) renders the ring basic ,p0 e ,p0 e
R- C + Nu ---+R - C +X
(d) deactivates the ring towards nucleophilic substitution. '-x '-Nu
84. The increasing order of stability of the following free
is fastest when X is
radicals is 12006)
(a) OCOR (b) OC 2 H5 (c) NH 2 (d) Cl
(a) (C6H5)2CH <(C6Hs>J C<(CH3)3 C<(CH3)2CH
90. Consider the acidity of the carboxylic acids :
(b) (C~)2CH < (CH3)3 C <(C6H5)2C H <(C68s)3 C (1) PhCOOH
(2) o-NO2C6H4COOH
(c) (CH3)3C<(CH3)/:H <(C6H5)i<::H <(C6H5)3C
(3) p-NO2C6H4COOH
(d)(C6H5h C<(C6H5)iCH <(CH3)3 C<(CH3)iC:H (4) m-NOiC6H4COOH
85. CH 3Br+Nu - ----+CH 3 -Nu+Br- Which of the following order is correct? 120041
The decreasing order of the rate of the above reaction (a)2>4>1>3 (b) 2>4>3 > 1
with nucleophiles (Nu-) A to Dis 12006) (c) I >2>3>4 (d) 2> 3>4> I
[Nu- = (A) PhO-, (8) ACO-, (C) HO-, (D) CH 30-] 91. Which of the following is the strongest base? 12004)
(a)A>B>C>D
(c) D>C>A>B
(b) B>D>C>A

(d) D>C>B>A
(a)QNH, (b) o-NHCH 3

86.
9
CXMe ~ ..... Me
~
(c)O-NH 2
CH 3

OH /\
n-Bu Et 92. In the anion HCOO- the two carbon-oxygen bonds are
The alkene formed as a major product in the above found to be of equal length. What is the reason for it?
12003)
elimination reaction is 120061

(a)
UMe (b)
OMe (a) The C = 0 bond is weaker than the C - 0 bond
(b) The anion Hcoo- has two resonating structures
(c) The anion is obtained by removal ofa proton from the
acid molecule
(d) Electronic orbitals of carbon atom are hybridised
(c)M~ (d) Ctti=aii
93. Arrangement of (CH3)F - , (CH3)iCH- , CH3 - C"2 - when
87. Due to the presence of an unpaired electron, free radicals
attached to benzyl or an unsaturated group in increasing
are: 120051
order of inductive effect is (2002)
(a) cations (b) anions
(a) (CH3)3C - < (C~)2CH - < CH3- CH2-
(c) chemically inactive (d) chemically reactive
(b) CH3--CH 2- <(CH3)iCH - <(CH3)3C-
88. The decreasing order of nucleophilicity among the
(c) (CH3)2CH- <(CH3)3C -< CH3 -C"2 -
nucleophiles is 120051
(d) (CH3)F- <CH3C8i - <(CH3)2CH -
(A) CH 3c-o- (B) CH3O- 94. The functional group, which is found in amino acid is
II (a) - COOH group (b) - N"2 group (2002)
0
(c) - CH 3 group (d) both (a) and (b).
 7. (d) lUPAC name: 4-Bromo-3-methylpent-2-ene
OH
I. (c) ICH3 CH

5
NH2
H~~

2. (b)
0 2N

* CHO
5-Am ino-4-h ydrox ymethy 1-2-nitrobenza ldeh yde
8. (d)
5CH Br
3

0
II 4-Ethyl-3-methylhex-2-cne
C - OH
9. (b)
6

Br 5
4
4-Bromo-2-methylcyclopentane carboxylic acid
2-Ethyl- I, l-dimethylcyclohexane
3. (c) 6
CHO
CH3

½:H I
5 4
I
10. (b) H3C - C - CH2 - CH = CH2
I
CH 3
3 2 I

(2, 5-dimethyl 1-6-oxo-hex-3-enoic acid)

4, 4 - Dimethylpentene

CH3 H sp2 sp sp 2 H
1 2 3 4 sl 6 7 11. (b) ""-... C = C = C /
4. (d) H2C = CHiHiH-CH-C CH = H/ ""-...H
CH 3 CH 2 CH 3
I
I
CH 2
I 2
12. (b) CH CH - CH-CH-CH CH
3 4 5 6
3 2 2 3
I
CH 6H2
3
I
3. S-dimethyl-4-propylhept-l-en-6-yne CH 3
3-Ethyl-4-methylhexane
s. (b) 13. (a) Ethers, due to absence of delocalized pair of
electrons do not show resonance.
14. (d) l, 2-Epoxy propane is the correct IUPAC name of
given compound.
~Cl
CH3 I
IS. (a) CH3'--._2 3/H
2-Chloro-l-methyl-4-nitrobenzene
.,,,c =c, 4 s 6 ,
H/ '- C = C - CH 2CH 3
6. (c) (E) - 2 - hepten - 4 - yne
~H
16. (a) In l, 2-dichlorobenzene the two dipoles are at 60°
3-Hydroxy-4-methyl pcntanoic acid
(i.e. unsymmetric). Thus possesses dipole moment.
 28. (b)
17. (a) CH 3
I ~ 3
H3C- C - CH3
I
CH 3
Ncopcntane
a a
or 2.2- Dimethylpropane Both substituents are same
(Isomer not possible)
18. (a) The correct order of priority for the given functional 29. (d) COOH
group is
H~OH
0 0
II II H---fL-CI
- COOH > - S03H > - C- NH2 > - C- H
CH3
CH 3 At(2),

19.
7 6
(a) CH-CH-CH-C-CH-CH-CH
S 41 3 2 I
®\
~
3 2 2 I 2 3
1
CH3 CH2CH3
3-Ethyl-4.4-dimethylheptanc

Cl ·s 'configuration

20. (a)
6

5 O 4

3-Bromo-1-ehlorocyclohexene
Br

M
21. (a) • R•configuration
H
I
HO JO. (c) H3C-C=CH-CH2Ph
In l-phenyl-2-butene, the two groups around the doubly
3, 3-Dimethyl • I cyclohexanol
bonded carbons are different. This compound can show
cis-and trans-isomerism.
0 0
II
sp3sp3 spJ II 31. (d) The optically inactive compound must contains achiral
22. (a) H3C - C -CH 3 CH3-C-OH ; carbon atom(s). Option (d) contains achiral carbon atom
sp 2 sp2 a a
Acetone Acetic acid I I
CH 3 -C-CHO CH 3 -CH 2 -C-CH 3

spJ
0
II ~ ~
CH3 - C - NH2 2- Chloropropanol 2-Chlorobutane
sp2 (chiral) (chiral)
Acetonitrile Acetamide
Cl CH3
I I
23. (a) CnH2n02 is general formula for carboxylicacid CH3 -CH2 -CH2 - C-CH3 CH3 -CH2 -C-CH3
I I
H Cl
0 CH3
I 211 31 4 2-Chloropentane 2-Chloro-2-methylbutane
24. (c) CH3-C- CH-CH3 (chiral) (achiral)

3-Methyl-2-butanone ~=~
25. (c) The correct name is 3 - methylbutan - 2 - ol are same
(2)
26. (b) lo molecules (a), (c) and (d), the carbon atom has a
multiple bond, only (b) has sp3 hybridisation.

27. (b) Enolic form of acetylacetone (b) is quite stable due to

H-bonding which leads to stable 6-membered ring. (3) (4)
I (5)
The possible structural isomers = 5
33. (a) Pentan-2-one and pentan-3-one are position isomers. 42. (b) The absolute configuration is (R, R)
(b), (c), (d) contain different compounds aldehyde and (use priority rules to get the absolute configuration)
ketones. These exhibit functional group isomerism. 43. (b) Chiral conformation will not have plane of symmetry.
34. (c) Optically active compounds contain an asymmetric Since twist boat does not have plane of symmetry, it is
(chiral) carbon atom (a carbon atom attached to four chiral.
different atoms or groups). Therefore, all acids except
maleic acid exhibit optical isomerism. 4
35. (d)
36. (b) Five cyclic structures are possible for C4 H6 . These
are as following:

□~ L 5

44. (b) The organic compounds which have chiral carbon

atom (a carbon atom attached to four different groups or
Cyclobutene 2-methyl I-methyl atoms) and do not have plane of symmetry rotate plane
cyclopropene cyclopropene
polarised light.

L
CHO

methylene
[SJ
bicyclo
HO-C- H
1.
I
CH 2OH
(• is asymmetric carbon)

cyclopropane [I , I .OJ butane

37. (d) Maleic acid and fumaric acids are geometrical H H H
isomers. 45. (a)
H - C - COOH H - C - COOH
II II 6-
H - C - COOH HOOC - C - H .F
Maleic acid Fumaric acid +
38. (c) When either of the two forms of glucose is dissolved
in water, there is change in rotation till the equilibrium Due to hydrogen bonding between H & F gauche
value of+ 52.5°. This is known as mutarotation conformation is most stable, hence the correct order is
Eclipse, Anti, Gauche
a- D( +) Glucose .:== Equilibrium mixture
+ 111.5° +52 .5° Cl Cl
.:== J3--D-(+)Glucose 46. (c) CH 3 -t-f CH 3
, 2, 3-Dichlorobutane exhibits optical
+ 19 .5° H H
isomerism due to the presence of two asymmetric carbon
H atoms.
I
39. (c) H2C = HC - •
C - CH2 -CH3 47. (b) Note: Compounds containing two similar chiral C-
I atoms have plane of symmetry and can exist in meso form
CH 3 too.
3- Methyl-1-pentene
CH3
(b)
--~ "±<:'-·
40.
plane of symmetry
H+-CI
CH3
cis-2-Butene trans-2-Butene meso-2, 3-Dichlorobutane
• 48. (a) Only 2-cylcopropylbutane has a chiral centre.
41. (b) CH 3 - CH =CH - CHCH 3
I H
OH 1.
It exhibits both geometrical as well as optical isomerism. CH 3 - C
I
- <]
cis-R cis-S C2Hs
trans-R trans- S
49. (c) 1-chloropentane is not chiral while others are chiral in I 2 3 4 5
ClCH2CH = CHCHCH 3
nature
I
Cl
(d)
S3. (d) A mixture of equal amount oftwo enantiomers is called
a racemic mixture.
54. (d) Stereoisomerism, isomers differ in the arrangement of
1.2 3 4 5 groups in space. The two structures show sterioisomerism.
H3CCHCH2CH 2CH 3 Structure I shows geometrical isomerism as it contains
ti (b)
two different atoms or groups Hand CH 3 attached to each
carbon containing double bond.
2 3 4 5 H3~ /CH 3 H "- /CH 3
CIC~C"2C1½C~CH3 /C = c , _/C = C"-
H H H3Lv H
(c) 1ra,1s-butenc
cis-butcne
Structure D shows optical isomerism as it contains a chiral
carbon (attached to four different groups) atom.
CH 3 CH 3
•I I.
H-C-OH HO-C-H
I I
CH2CH 3 CH 3CH 2
SO. (a) Butyl alcohol (two enant iomcrs)
SS. (SO)
Mass of organic compound = 1.6 g
Mass ofAgBr = 1.88 g
0 CH3 1.88
II I ~ Ch ira
' I
Moles of Br= Moles of AgBr = - = 0.0 I
CH3 - C- C~C2Hs carbon 188
I Mass of Br = 0.01 x 80 = 0.80 g
H
(II) 0.80x 100
o/ofBr=---= 50%
/O 1.60
H
le Alternate Method :
H- C~
I Achiral o/
10 0
fB r = _
Wt._
of___;;__
AgBr X -
Molar mass of Br
- - - - - X 100
H carbon Wt. ofO.C. AgBr
(Ill)
1 88 80
= · X X 100 = 50%
CH 3 1.6 188
I S6. (d) Acidic strength oc - 1, - M effect. Due to strong - I,
C2H5 - C - C2H5 and - M effect of three - COOCH3 groups, it has most
~ ~Achiral acidic Hydrogen.
carbon S7. (d) Glycerol can be separated from spent-lye in soap
(IV)
industry by using reduce pressure distillation technique.
S1. (c) Both differ in the arrangement of group in space,
therefore grouped under sterio-isomerism. S8. (c) Basicity order can be determined by the cummulative
effect of the factors on the electron density of concerned
I 2 3 4 5
S2. (c) CICH =C CH2CH 2CH 3 atom.
I S9. (a) Liquid having lower boiling point comes out first in
Cl fractional distillation. Simple distillation can't be used as
(a)
boiling point difference is very small.
Cl 3-Methylpantane will show greater boiling point (63°C)
I 2 31 4 5 comparative to isohexane due to symmetrical structure.
Cl CH 2CH =C-CH 2CH 3 Therefore isohexane distilled out first.
(b)
60. (b) Electron withdrawing group like (NO2) increase stability
I 2 3 4 5
of alkoxide ion by dispersal of negative charge.
Cl2C = CHC"2CliiC~
(c)
 In (B) and (C) structures negative charge is in conjugation
with double bond and also stabilised by electron
withdrawing effect of nitro group. ~ H + CJ-',,,!____
61. (d) Higher the basicity of a base, stronger will be its 2 5
nucleophilic character. Further a stronger base has a 65. (b) Since, adsorption of I > II, I is firmly attached to
weaker conjugate acid. The acidic order of the conjugate column (stationary phase). Hence, it moves slowly and
acid of the given bases is will cover little distance, while II is loosely attached to
Hp' > C}\S03 H> C}\COOH> 8i0 column (stationary phase). Hence, it moves raster and will
Thus the increasing order of the basic nature or cover large distance.
nucleophilicity of the given species is 66. (b) Partition chromatography is the process of separation
whereby the component of the mixture get distributed into
H20 < CH3S03 < CH3Coo- < 0H - two phases that may be liquid-liquid, liquid gas but not to
(ii) (iii) (i) (iv)
solid-gas. Thus, it is not possible that the stationory phase
62. (c) is a finally devided solid adsorbent in partition
chromatography.
(i) 67. (a)
(I) CflsOH Hydrogen bonding
+ Hydrogen bonding > dipole-dipole
~ ANH ~ ./2NH2
(ii) / ~ Protonation➔ / ~ Dipole-dipole
(s/) C2HsCl is more polar than C2IfsOCH3so,
(iii) dipole-dipole C2H5Cl > dipole-dipole

A NH2

~NH
Protonation (III) C2HsCH3
C2HsOCH3
Weak vander Waals yarces
(IV) C28s~ Dipole-dipole
Thus, boiling points order is -
[ Equivalent resonance) (Ill)< (IV)< (II)< (I).

~ NHCH3
Protonatio'!.+ ~ +
(iv) NH 2 -CH3 68. (b) When the given mixture is shaken with I M HCl, amine
(2° and sp 3) $

Hence, correct order ofbasicitywill be: (ii)< (i) <(iv)< (iii). get protonated and becomes cation (R 2N H2 ), which
63. (c) Among the substituents attached to the given does not dissolve in organic solvent but usually dissolve
compounds, fluorine has maximum electronegativity. so in H20 due to its charge. So, shaking with aqueous HCI
it will push electron pair towards itself. In option (b), will pull amines into the aqueous phase and leave all other
the two F groups are attached opposite to each other, compounds in organic layer.
thus net dipole moment will cancel out and reduce its 69. (b) Since SN I reactions involve the formation of
polarity. In option (d), the F groups are attached in carbocation as intermediate in the rate determining step,
slightly opposite direction, thus this also decreases its more the stability of carbocation higher will be the
polarity. But in option (c), the compound has the two F reactivity of alkyl halides towards SN 1 route.
groups along same direction, thus net dipole moment
Since stability of carbocations follows order.
will increase in this direction and therefore it will exhibit (I) (I)
maximum polarity. Hence the compound in option (c) CH3 - C8i - CH 2 <CH3 - CH - CH2 - CH3
has maximum polarity. I• carbocation 2° carbocation
64. (b) The lone pair of electrons on 0 2 is involved in (I)

resonance with C = C. Hence 0 2 will not be protonated. <p - ~C0 - C6H4 - CH 2

Max. stable due to +M effect of - OCH 3 group.
The lone pair of electrons on 05 is not involved in
resonance with C = C. Hence, 05 will be protonated.
Chloride ion will then attack least substituted C atom (C6)

~ 6-fil4
70. (d) Q 0

is nooa,-omatic and hence lea~ reasonance

~~~
2 5 stabilized, whereas other three are aromatic.
71. (b) Pent-I-ye and glycerol are separated by distillation 76. (a) 3° carbocations are most stable.
under reduced pressure. 77. (a) - Cl and - CH3 groups are o and p directing. They are
Under the reduced pressure, the liquid boil at low electron releasing due to + M and hyperconjugation
temperature and the temperature ofdecomposition will not
effects. Further since such groups increase electron
reach. e.g. glycerol boils at 290 °C with decomposition but
at reduced pr~re it boils at 180° C without deccmposition. density in the nucleus, they facilitate further electrophilic
substitution and hence known as activating group. The
o-Q-~ o/H activating effect of these groups is in order of- CH3 > - X
72. (d) / but chlorine exceptionally deactive the ring due to strong
H -
- I effect. Hence, it is difficult to carry out substitution in
chlorobenzene than in benzene. Further - NO 2 is a
/s-Q-s/H deactivating group, hence deactivates the benzene
H - nucleus, i.e. hinder the further substitution. Thus
In both the molecules the bond moments are not cancelling nitrobenzene undergo electrophilic substitution with a
with each other and hence the molecules has a resultant
dipole. great difficulty, hence the correct order will be

73. (d) Ph 3 C• is more stable than (CH 3 ) 3 C• because

•
resonance stabilisation effect in Ph C is more pronounced
3
as compared to hyperconjugation stabilisation effect in
•
(CH3)] C, overall stability order among free radical is:
(B) (A) (C) (D)
Triphenylmethyl > benzyl > allyl > tertiary alkyl >
78. (b) Since the leaving group breaks away as a base, it is
secondary> primary> methyl > vinyl
easier to displace weaker bases as compared to stronger
74. (c) Carbocationsareplanar, hence can beattackedoneither bases. Thus less basic the substituent, the more easily it
side to foon racernic mixture. is displaced.
EB
Since the basic strength of the given groups is in order.
CI-CH-CH3 ~~~~e , Ph-CH-CH 3 +SbCl 6~ J- < Br<CI-
I (carbocation) Thus the order of halogen leaving groups is
Ph J- >Br>Cl-
(- ) Ph- CH -CH 3 +SbCl5
79. (d) - OCH3 and - CH3 groups are activating group
I
Cl while - Cf3 is a deactivating group. Thus order is
( d + l ) mixture
75. (d) Higher stability of allyl and benzyl carbocations is
due to dispersal of positive charge by resonance
~EB EB
CH2 = CH-CH2 ~CH2 -CH= CH 2
Resonating structures of ally I carbocation

80. (d) The corresponding conjugate acid are

CH 3COOH > CH = CH > NH 3 > RH
Most acidic Least acidic
:. the correct order ofbasicity is
Resonating structures of benzyl carbocation
whereas in alkyl carbocations dispersal of positive charge RCOO- < CH = C- < NH 2- < R -
on different hydrogen atoms is due to inductive effect. 81. (b)
Hence the correct order of stability will be
/Cl

6
EB
<c-cl > C6HsCH2
'c1
- ve charge - M effect +I effect ofCH 1 group
>CH 2 =CH-~H 2 >CH3 -CH 2 -~H 2
highly dispersed delocalises intensifies the - ve charge
Benzyl. Ill Allyl, I Propyl. II due to - I effect - ve charge
82. (b) ln option (b) the complex formed is with benzene Hence based on the above facts, the correct order of
whereas in other cases it is formed with nitrobenzene with nucleophilicity will be
- N02 group indifferent positions (o-, m-,p-). The complex CN - > CH 30 - > CH 3COO- > H3CC 6H4S03
formed with nitrobenzene in any position of - N0 2 group (C) (8) (A) (D)
is less stable than the complex formed with benzene, so 89. (d) - Cl is the best leaving group among the given
the most stable complex has lowest energy. options.
83. (a) Nitro group is electron withdrawing group, so it 90. (d) In carboxylic acids, presence of electron withdrawing
deactivates the ring towards electrophilic substitution. substituent e.g. - N0 2 disperses the negative charge of
84. (b) Theorderofstabilityoffreeradicals the anion and stabilises it and hence increases the acidity
. . .
(C 6H5 )] C >(C6H5 )i CH> (CH 3h C > (CH 3 )i CH
. of the parent acid.
Further o-isomer will have higher acidity than
The stabilisation of first two is due to resonance and last corresponding m-and p-isomers due to ortho and high
two is due to hyper conjugation. inductive effect of - N0 2 group. Since nitro group at p-
8S. (c) position has more pronounced electron withdrawing than
CH3CO(r <C6Hs0- <OH- < OCH3 - N02 group at m-position, hence the correct order is:
e -s are delocalised Max. e - density on 0
86. (d) Hofmann's rule: When theoretically more than one
type of alkenes are possible in eliminations reaction, the
alkene containing least alkylated (least substituted) double
@H< ~N0
2
bond is formed as major product. Hence

~
CC M
/N~ e
n-Bu
e
EB ........;;;;...

CH 24 yH 2
CCMe
N- Me
I
< ~H<@HN02

"1 n-Bu N0 2
H,--OH - +
CH 2 = CH2 91. (d) Lone pair of electrons present on the nitrogen of
benzyl amine is not involved in resonance.
Note: Therefore less sterically hundred 13-hydrogen is
removed. 92. (b) Hcoo- exists in following resonating structures
87. (d) Free radicals are electrically neutral, unstable and very
reactive on account of the presence of odd electrons.
o 00
II I
88. (a) In moving down a group, the basicity and H-c-o- ~ H - C =0
nucleophilicity are inversely related, i.e. nucleophilicity Hence in it both the carbon oxygen bonds are found equal.
increases while oosicity decreases. In going from left to right
93. (b) - CH3 group has + I effect, as number of- CH3 group
across a period, the basicity and nucleophil icity are directly
related. Both of the characteristics decrease as the increases, the inductive effect increases.
electronegativity of the atom bearing lone pair of electrons Therefore the correct order is
increases. Ifthe nuclcophilic centre oftwo or more species is CH3- C8i- < (CH3) 2CH- < (C~)3 C-
same, nucleophilicity parallels basicity, i.e. more basic the 94. (d) Amino acids contain - NHi and - COOH groups, e.g
species, stronger is its nucleophilicity. glycine HiNCHiCOOH.