CLS JEEAD-18-19 XI Che Target-4 SET-2 Chapter-12 PDF

Chapter 12
Organic Chemistry : Some Basic

Principles and Techniques
Solutions
SECTION - A
Objective Type Questions (One option is correct)
Structure, Classification, Nomenclature of Organic Compounds

1. The IUPAC name of the compound CH3 CH3
CH
CH3
CH3—CH—C—CH
CH3
CH3 CH
CH3 CH3
(1) 3-diisopropyl-2,4-dimethylpentane (2) 2, 4-dimethyl-3-diisopropylbutane

(3) 2, 4-dimethyl-3-3-bis(1-methylethyl) pentane (4) None of these
Sol. Answer (3)
5 carbon in longest chain.
Me
2. The IUPAC name of the compound
Et
(1) 3-methyl-6-ethylcyclohexene (2) 6-ethyl-3-methyl cyclohexene
(3) 3-ethyl-6-methyl cyclohexene (4) 6-methyl-3-ethyl cyclohexene
Sol. Answer (3)
Priority of Et is alphabetically higher.
Isomerism
3. Compound having molecular formula C5H12O cannot show
(1) Tautomerism (2) Position isomerism
(3) Metamerism (4) Functional isomerism
Sol. Answer (1)
Factual
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56 Organic Chemistry : Some Basic Principles and Techniques Solutions of Assignment (Set-2)
4. Which will have the highest melting point?
(1) (2) (3) (4)

Sol. Answer (3)
Due to symmetrical structure neopentane will have most efficient stacking and hence highest melting point.
5. Three dimensional arrangements which can be interconverted into one another due to rotation along a single
bond are known as
(1) Conformers (2) Diastereomers (3) Chain isomers (4) Positional isomers
Sol. Answer (1)
Conformers are formed due to rotation about single bond
O
6. The compounds and are
O
(1) Chain isomers (2) Metamers (3) Position isomers (4) Both (1) & (2)
Sol. Answer (4)
Both have different carbon chain length.
7. What is the index of hydrogen deficiency in the molecule C12H17NO?

(1) 4 (2) 5 (3) 6 (4) 7
Sol. Answer (2)
17  1
Index of hydrogen deficiency  (12  1) 
2
= 13 – 8 = 5
8. Which of the following compound cannot have a  bond?

(1) C10H21N (2) C7H12 (3) C20H40Cl2O (4) C30H50Br2O2
Sol. Answer (3)
Degrees of unsaturation in compound C 20 H 40 Cl 2 O is zero therefore the compound cannot have a
 bond.
9. Which of the following compounds will have highest enolic content?
(1) (2) CH3COCH2CHO (3) CH3CHO (4) CH3COCH3
Sol. Answer (1)
O O H
H
mos t stable enol

form s tabilized by
Aromatic character
10. The total number of structural monochloroderivatives possible in C5H12 is

(1) 6 (2) 7 (3) 8 (4) 5
Solutions of Assignment (Set-2) Organic Chemistry : Some Basic Principles and Techniques 57
Sol. Answer (3)
n-pentane, isopentane and neopentane form 3, 4 & 1 structural monohaloderivatives respectively.
Electronic displacement, Resonance, Aromaticity

11. In which of the following all electronic effects namely inductive, mesomeric and hyperconjugative effects are
present?
O
O
CH3
(1) (2) (3) (4)
H3C CH3
O
Sol. Answer (4)
In (1), (2) and (3) hyperconjugate effect is absent.
12. At conjugated position – NO imparts

(1) + M and + I effect (2) – M and – I effect (3) + M and – I effect (4) – M and + I effect
Sol. Answer (2)
 O (delocalization of p of double bonded N is difficult)
–N
13. In the given anion, –ve charge is delocalized on
(1) One atom (2) Three atom (3) Four atom (4) Five atom
Sol. Answer (3)
(2)
– (1)
(3)
(4)
14. Which of the following group will have the strongest electron donating mesomeric effect?
H
 O Me N O
(1) N (2) N (3) C=O (4) O–C
O Me H3C R
Sol. Answer (2)

Electron donating mesomeric effect of a group depends upon size, electronegativity and lone pair availability
of key atom.
15. Which of the following organic molecule cannot form hydrogen bond in pure state but can form the same in
water?
O
(1) (CH3CH2)2NH (2) CH3CHO (3) CH3CH2COOH (4) CH 3–C –NH 2
Sol. Answer (2)
H 3C H
  
C = O ----- H — O
H
16. Which of the following is correct order of dipole moment of o, m and p-methyl benzonitrile?
CH3 CH3 CH3 CH3 CH3 CH3

CN CN
(1) > > (2) > >
CN CN
CN CN
CH3 CH3 CH3 CH3 CH3 CH3

CN CN
(3) > > (4) > >
CN CN
CN CN
Sol. Answer (2)
CH3– is electron donating group and –CN is electron withdrawing group   12  22 – 212cosθ
17. Among the following, the most stable carbocation is

(1) CH3  CH CH3 (2) (3) (4)
Sol. Answer (2)

+
is an aromatic cation.
18. Resonance is not possible in
(1) (2) NH3 (3) NO2 (4) BH2

O
Sol. Answer (2)
Nitrogen cannot form five bonds due to absence of vacant low energy d orbital
19. Which of the following hydrocarbon is most acidic?
(1) (2) (3) (4)
Sol. Answer (1)
is most acidic because it generates most stable aromatic conjugate base.
20. Which of the following represents the correct order of stability of the given carbocations?
CH2
I
II III
(1) III > I > II (2) I > III > II (3) III > II > I (4) II > III > I
Sol. Answer (1)
IIIrd is aromatic (most stable) and IInd is antiaromatic (least stable)
21. In which of the following molecules positive charge is not delocalized because of resonance?

NH NH2

Me 
Me
(1)  C (2) (3) C—N (4) C
H3N NH2 Me Me NH2 NH2
Sol. Answer (1)
Nitrogen atom cannot form five bonds due to absence of vacant d-orbitals.
22. The number of sp2 hybridised carbon in one benzyne is

(1) 4 (2) 5 (3) 6 (4) 3
Sol. Answer (3)

. All carbon atoms are sp2 hybridised.

+
 Acidity and Basicity
23. In which of the following reactions equilibrium will shift towards right?
+ NaHCO3
(1) (2) C C—H + NaOH
H H
O
OH
C
(3) + NaHCO3 (4) OH
+ NaHCO3
Sol. Answer (4)

NaHCO3 a weak base can deprotonate a very strong benzoic acid. Other acids are very less acidic, hence
cannot be deprotonated by NaHCO3
O O
O
C H C
O C ONa
+ NaO OH
+ .
O
CO2 + H2O C
HO OH
24. Strongest and weakest acid among the following is

CH3 — NO2 CH3 — CHO CH3 — F CH3 — CN
I II III IV
(1) I and II (2) III and IV (3) III and II (4) I and III
Sol. Answer (4)

Conjugate base of nitromethane (CH3—NO2) is stabilized by very strong – I and – M effect of – NO2 group
O O O
H—CH2—N CH2—N CH2—N
O O O
B
Very stable
conjugate base
Conjugate base of CH3—F is only stabilized by – I effect of F atom hence it is less stable and CH3F is
least acidic.
25. Correct order of acidic strength for the given species
CH3—C N—H CH3—CH2—CH3 CH3—C C—H CH2—H
I II III IV
(1) I > II > IV > III (2) II > IV > III > I (3) III > I > IV > II (4) I > III > IV > II
Sol. Answer (4)
CH3—C — CH3—C —
B
— N—H —N
highly unstable More stable
due to presence
of positive charge
on highly en. sp—N
26. Which of the following will have weakest indicated C—H bond?
CH3
H3C C
H3C
(1) O2N CH2—H (2) CH2—H
H3C
H3C C
H3C
CH3
CH3
C
CH3
(3) CH2—H (4) CH3—H
CH3
C
CH3
CH3
Sol. Answer (3)
CH3
CH3
C
CH3
CH2—H
CH3
C
CH3
CH3
Therefore, indicated C—H bond in (3) is weakest.
27. Which of the following compounds will not dissolve in aqueous NaOH?
R O
O H
O S
H C H
(1) (2) OH (3) (4)
OH OH
HO
Sol. Answer (3)
OH is least acidic.
28. Most acidic species among the following is
O O S S O O
(1) (2) (3) (4)
O S O O
Sol. Answer (2)
Because its conjugate base is stabilized by p-d back bonding.
29. Which of the following is the strongest base in water?
(1) (2) NH2 (3) (4)

N
Sol. Answer (4)

In this compound lone pair of N is nondelocalized. Above all, the N atom is sp3-hybridized and hence, this
N is most basic.
N
3
sp
H
30. Which of the following is most acidic?
NH2 OH NH2
(1) (2) NH2 (3) CH3 – O – H (4) C
N
H H2N NH2
Sol. Answer (2)

It forms most stable conjugate base
31. Most acidic species among the following is

O
(1) CH3 – C – CH3 (2) CH3 – O – H (3) CH3 – C  C – H (4) H
Sol. Answer (2)
—O—H bond is most polar due to maximum electronegativity difference
Reaction Intermediates
32. Which of the following experimental techniques can be used to detect carbon free radicals in a reaction mixture?
(1) Magnetic susceptibility method (2) Polarimetry
(3) NMR-spectroscopy (4) IR-spectroscopy
Sol. Answer (1)
This method indirectly gives some information about the presence of unpaired electrons.
33. Which of the following reactions will not generate a carbanion?
(1) NaOEt NH 2
(1) (2)
Et-OH NO 2
O
SbF5
(3) (4) CH3 — C C — H 
NaNH2 /NH3

F
Sol. Answer (3)
O O
H SbF5 + [SbF6]
–
H NaOEt +
F
O O
NH2
CH3—C C—H CH3—C C
34. Out of the given reactive intermediates which will be attracted towards the magnetic field?
(1) Carbocation (2) Carbanion (3) Carbon free radial (4) Nitrene
Sol. Answer (3)
Carbon free radicals will have unpaired electrons and hence it will be attracted towards the magnetic field.
35. Which of the following species cannot behave as electrophile?

(1) BCl3 (2) AlCl3 (3) NH4+ (4) SO3
Sol. Answer (3)

NH4 does not have vacant orbital of appropriate energy.
36. Least stable carbocation among the following is

CH3
H3C – C – CH3 CH3
(1) (2) (3) CH3 – C – CH3 (4) CH

H2C CH2
CH3
CH2 CH2
Sol. Answer (4)
It has less number of resonating structures and less hyperconjugation effect.
37. The most stable free radical is _________
CH
(1) (2) (3) (4)
Sol. Answer (2)

Due to resonance and hyperconjugation both.
38. Which of the following double bond in the given molecule is most reactive towards a strong protic acid?
Me A C
Me
B D
Me
(1) A (2) B (3) C (4) D
Sol. Answer (1)
Attack of H+ on double bond (A) gives most stable carbocation.
CH 3
+ CH3
CH3
39. Among the following,
Cl Cl Cl
I II III
the correct order of reactivity of chloride is
(1) I > II > III (2) III > II > I (3) II > I > III (4) II > III > I
Sol. Answer (4)
Stability order is
+ + +
(Antiaromatic)
40. Correct stability order of the given free radicals is
CH3 CH3
(1) CH2 > > CH3— C > (CH3)2CH (2) > CH2 > CH3–C– > (CH3)2CH
CH3 CH3
CH3 CH3
(3) > CH3–C– > CH2 > (CH3)2CH (4) CH2 > CH3–C– > (CH3)2CH >
CH3 CH3
Sol. Answer (2)

Allyl C—H bond has lesser bond dissociation energy than benzylic C—H bond and hence corresponding allyl
free radical is more stable.
41. In which of the following homolytic bond fission takes place?

(1) Alkaline hydrolysis of ethylchloride (2) Addition of HBr to double bond
(3) Photochlorination of methane (4) Nitration of benzene
Sol. Answer (3)
Halogenation of methane proceeds through free radical mechanism. In the initiation step of this reaction. Free
radicals are generated through homolysis of a bond.
Initiation
 or h
Cl — Cl Cl + Cl
⎡ Purification, Separation, Quantitative and ⎤

⎢qualitative analysis of organic compounds ⎥
⎣ ⎦
42. Which of the following reagents can be used to separate benzoic acid from a mixture of Benzoic acid, Phenol,
Benzaldehyde and Toluene?
(1) aq. HCl (2) aq. NaHCO3 (3) Diethyl ether (4) NaOH
Sol. Answer (2)
When benzoic acid reacts with NaHCO3 it forms water soluble sodium benzoate and hence through extraction.
It can be separated.
43. A mixture contains four solid organic compounds A, B, C and D. On heating, only C changes from solid to vapour
state. The compound (C) can be separated from the mixture by
(1) Distillation (2) Kinetic resolution (3) Crystallization (4) Sublimation
Sol. Answer (4)
Solid is directly converted to vapour.
44. Which of the following compound will give blood red colour while doing the Lassaigne’s test for N?
NH2
(1) (NH2)2 C O (2) H2N (C6H4) SO3H (3) C6H5SO3H (4)

Cl
Sol. Answer (2)

When both N and S is present in a compound. It gives blood red precipitate in Lassaigne’s test.
45. Which of the following compounds will give negative Lassaigne’s test for Nitrogen?
(1) NH2 (2) N N
NO2
(3) N (4)
Sol. Answer (2)

It is azo compound. Azo compound gives negative Lassaigne’s test.
46. The number of structural isomers for C6H14 is [IIT-JEE-2007]
(1) 3 (2) 4 (3) 5 (4) 6
Sol. Answer (3)
47. Among the following, the least stable resonance structure is [IIT-JEE-2007]
 O O O O
  
(1) (2) N (3)  (4)  
N  N N
| | | |
O O O O
Sol. Answer (1)
48. Hyperconjugation involves overlap of the following orbitals [IIT-JEE-2008]

(1) – (2) –p (3) p – p (4) –
Sol. Answer (2)
Hyperconjugation involves -p conjugation.
49. The correct stability order for the following species is [IIT-JEE-2008]
  
O O 
(I) (II) (III) (IV)
(1) (II) > (IV) > (I) > (III) (2) (I) > (II) > (III) > (IV) (3) (II) > (I) > (IV) > (III) (4) (I) > (III) > (II) > (IV)
Sol. Answer (4)
I & III are stabilized by resonance, hyperconjugation and + inductive effect.
 order is (I) > (III) > (II) > (IV)
50. The correct acidity order of the following is [IIT-JEE-2009]
OH OH COOH COOH
Cl CH3
(I) (II) (III) (IV)
(1) (III) > (IV) > (II) > (I) (2) (IV) > (III) > (I) > (II) (3) (III) > (II) > (I) > (IV) (4) (II) > (III) > (IV) > (I)
Sol. Answer (1)
COOH COOH OH OH
> > >
CH3 Cl
(+I effect) (–I effect)
51. The IUPAC name of the following compound is [IIT-JEE-2009]
OH
CN
Br
(1) 4-Bromo-3-cyanophenol (2) 2-Bromo-5-hydroxybenzonitrile
(3) 2-Cyano-4-hydroxybromobenzene (4) 6-Bromo-3-hydroxybenzonitrile
Sol. Answer (2)
OH
CN
Br
2-Bromo-5 hydroxy benzonitrile.
52. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is
[IIT-JEE-2009]
H H
1 + 5
2 4
H3C—C —C—C
3
—CH3
HO H CH3
(1) CH3 at C-4 (2) H at C-4 (3) CH3 at C-2 (4) H at C-2
Sol. Answer (4)
H H H H
1 + 5 +
2 4
H3C—C —C—C
3
—CH3 CH3—C—C—C—CH3
HO H CH3 :OH H CH3

More stable resonance
stabilized carbocation
53. The correct stability order of the following resonance structures is [IIT-JEE-2009]
 –  – –  – 
H2C  N  N H2 C— N  N H2 C— N  N H2 C— N  N
(I) (II) (III) (IV)
(1) (I) > (II) > (IV) > (III) (2) (I) > (III) > (II) > (IV)
(3) (II) > (I) > (III) > (IV) (4) (III) > (I) > (IV) > (II)
Sol. Answer (2)
Resonating structures having maximum number of covalent bonds are more contributing. Among
charge separated resonating structures, structures where opposite charge are close enough are more
contributing.
54. Among the following compounds, the most acidic is [IIT-JEE-2011]

(1) p-nitrophenol (2) p-hydroxybenzoic acid
(3) o-hydroxybenzoic acid (4) p-toluic acid
Sol. Answer (3)
O H O
–
C C

O –H O
H H
O O
Most acidic Stabilized by strong
intramolecular hydrogen
bonding
55. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) [IIT-JEE-2012]
(1) sp and sp3 (2) sp and sp2 (3) Only sp2 (4) sp2 and sp3
Sol. Answer (2)
H (sp) H
C=C=C
H H
(sp2) (sp2)
(Allene)
56. The order of basicity among the following compounds is [JEE(Advanced)-2017]

NH NH2
H3C NH2 N NH HN N
H2N NH
I II III IV
(1) IV > I > II > III (2) IV > II > III > I (3) I > IV > III > II (4) II > I > IV > III
Sol. Answer (1)
NH2
H2N NH
IV
Resonance with two NH2 groups increases electron density on 'N' of NH
NH
Lesser increase of electron density on = NH due to
only one resonance with one –NH2
CH3 NH2
sp2
N
N This LPe– is not available as it is involve in aromatic Sextet.

2
H 'N' is bonded to sp C on both sides.
III
N This LPe– is not involve in aromaticity. So more available

H
Also, 'N' is bonded to sp3 C on one side.
II
 IV > I > II > III
SECTION - B
Objective Type Questions (More than one options are correct)
1. Which of the following bicyclic compounds are isomers?
(1) (2) (3) (4)
Sol. Answer (1, 2, 3, 4)

All of them have same molecular formula hence, they are isomers.
2. Which of the following will involve homolysis of a bond?

O O
h
(1) Ph—C—O—O—C—Ph h (2) RO — Cl 
CH3
+ BuLi
(3) CH3—C—OH H (4)

CH3
Sol. Answer (1, 2)
O O O
h
Ph—C—O—O—C—Ph 2Ph—C—O
h
R—O—Cl R—O + Cl
3. Species which will exhibit geometrical isomerism among the following is/are
T D
CH3
H
C C C N—OH
(1) (2) Br (3) (4) N2H2
H 3C
H Me
Sol. Answer (1, 3, 4)
4. Which of the following molecular formula will exhibit functional isomerism as well as metamerism?
(1) C4H10O (2) C4H11N (3) C4H8O (4) C4H9Cl
For molecular formula C4H11N only saturated amines are possible (1°, 2° & 3° amines are functional isomers)
Molecular formula C4H9Cl only represents saturated alkyl chloride. Therefore metamerism is not possible.
5. Out of the given isomeric hydrocarbons which will undergoes rearrangement reaction in acidic medium?
(1) (2) (3) (4)
Sol. Answer (2, 3)
+H
(1)
Stable tertiary
carbocation
+H
(2)
Stable tertiary
carbocation
(No rearrangement
possible)
6. Which of the following carbocation is stabilised by resonance?


CH2
 
CH 3 
(1) CH2  CH — CH2 (2) C (3) C (4)
CH 3
Sol. Answer (1, 2, 3, 4)
7. Which of the following carbocations have potential to rearrange?
CH3 
   CH2
(1) CH3 — C — C — O (2) (3) — CH (4)
CH3 CH3
CH3 CH 3
+
CH3—C + CO
+
 CH3—C—C = O
CH3 CH 3
+
CH—CH3 +
CH3

+ +
CH2

8. Formic acid is more acidic than

(1) Benzoic acid (2) Acetic acid
(3) Phenol (4) Benzene sulphonic acid
In benzoic acid +R effect of benzene in acetic acid. +I effect of CH3–group and in phenol formation of less
stable resonating structures makes formic acid more acidic.
9. Which of the following will have C  O bond length almost similar to C — O bond length?
O O
O
(1) (2) (3) (4) O  C  O
Sol. Answer (1, 2)

–
O
–
O
+ +
Both are aromatic
10. The correct order of stability is/are

  
(1) HC  C  H2 C  CH  CH3  CH2 (2) HC  C > H C = CH > CH3–CH
2 2
CH2
  
(3) HC  C  H2 C  CH  CH3  CH2 (4)

 Due to percentage S-character (electronegativity) anion of sp hybridized carbon is most stable.
 Due to lower bond energy of allylic H as compared to benzylic H, allyl radical is more stable than benzyl
radical.
11. Which of the following is not stabilised by hyperconjugation?

Me Me

 
(1) CH3 (2) CH2 (3) (4) 
Me Me

 In CH3 and there is no  hydrogen
+
 In CH2 , stability is due to overlapping of p-orbital
12. Dichloro ethene shows

(1) Geometrical isomerism (2) Position isomerism (3) Metamerism (4) Chain isomerism
Sol. Answer (1, 2)
Cl
Cl – CH = CH – Cl can show geometrical isomerism and CH 2 CH is its position isomer
Cl
13. A compound having molecular formula C4H10O can show

(1) Metamerism (2) Functional isomerism (3) Chain isomerism (4) Position isomerism
Sol. Answer (1, 2, 3, 4)

All four isomerism are possible. Optical isomer is possible by 2-methyl-1-butanol.
14. Which of the following correctly represents the order of quality mentioned in bracket?
(1) sp – sp > sp2 – sp2 > sp3 – sp3 (bond energy) (2) sp – sp3 > sp – sp2 > sp – sp (polarity in bond)
(3) sp3 – s < sp2 – s < sp – s (% s character) (4) sp3 – sp3 > sp2 – sp2 > sp – sp (bond stability)
sp, sp2 & sp3 have 50%, 33% and 25% s-character.
15. Consider the following compounds
N N
H NH2
(I) (II) (III)
Which of the following statements are correct?

(1) I is more basic than II (2) II is more basic than I and III
(3) III is more basic than II (4) I is weakly acidic
Sol. Answer (2, 4)
Due to higher Kb for II, it is more basic than I and II.
16. Which of the following correctly represent the acidic strength of given acids?
(1) Cl3CH > F3CH (2) CH3COOH > CH3CH2OH
OH OH
(3) H2O > CH3CH2OH (4) >
NO2
Sol. Answer (1, 2, 3, 4)
CCl3 is more stable than CF3– due to presence of d-orbital in CCl3 hence CHCl3 is more acidic than CFCl3.
17. Which of the following correctly represents the stability of reactive intermediate?
+
(1) CH3–CH2 < CH3OCH2 (2)
CH2 CH2
CH3

(3) > (4) CH3–CH3–C  < CH3CH2
CH3
NO2 CH3


CH3 —O— CH2 is a resonance stabilized carbocation.
18. The correct order of basic strength in aqueous medium is/are

(1) (C2H5)2NH > (C2H5)3N > C2H5–NH2
(2) (CH3)2NH > CH3–NH2 > (CH3)3N
(3) CH3 – NH – CH2 – CH3 > CH3  CH  CH3 > CH3 – CH2 – CH2 – NH2
|
NH2
(4) C2H5 – NH2 > CH3 – NH2 > CH2 = CH – NH2
Sol. Answer (1, 2, 3, 4)
These orders are due to steric hindrance and different Kb value
19. Keto-enol Tautomerism is observed in

(1) C6H5–CHO (2) C6H5–CO–CH3
(3) (4) C6H5–CO–CH2–CO–CH3

NH2

C6H5 CHO has no –H. Therefore it will not exhibit tautomerism
O O H
H 2N H NH2
20. Which of the following can exhibit geometrical isomerism?
H H
(1) C6H5CH = N – OH (2) (3) (CH3)2C = C(CH3)2 (4)
Me Me
Sol. Answer (1, 4)
Ph OH Ph
C N and C N
H H OH
Geometrical isomers
H H H Me
and
Me Me Me H
Geometrical isomers
21. The compounds which cannot react with NaOH is/are

OH
(1) CH3  C  CH (2) NH3 (3) C2H5OH (4)
OH– cannot neutrallise CH3—C  CH, NH3 and C2H5OH due to their very low acidic strength (weaker acids
than H2O)
22. The hybridisation of N is correctly given in

(1) sp3 in acetamide (2) sp2 in pyridine (3) sp2 in pyrrole (4) sp in methyl cyanide
O
 

CH—C—NH
3 2 N N CH3 — C  N
 sp2 sp
sp 2
sp2 H
23. Which of the following Lewis structures are valid resonating structures for the azide ion?
N
– 
(1) N—N—N (2) N N N (3) N N N (4)
N N
Sol. Answer (1, 3)

2
N N N
Invalid resonating structure because of extension of octet around N.
N
N N Invalid structure because position N atom is changing as well as no. of -electrons are also
changing.
24. In the given compound the hybridisation states of C atom is/are not
(1) sp2 (2) sp3 (3) sp (4) dsp2

All carbon atoms are sp2 hybridised due to resonance.
25. In Lassaigne’s test, the sodium extract of an organic compound containing both N and S on treatment with FeCl3
solution produces a blood-red colour. The appearance of this blood red colour is due to
(1) [Fe(SCN)4]– (2) FeCl2(SCN) (3) [Fe(SCN)(H2O)5]2+ (4) Na4[Fe(CN)5NOS]
All of three are possible and (4) is Prussian blue coloured
26. Amongst the given options the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is(are) [IIT-JEE-2011]
H H H
(1) C—C (2) H—C C—C (3) H2C = C = O (4) H2C = C = CH2
H 2C CH2 CH2
Sol. Answer (2, 3)

H
C H
H
C
sp C C C O
2
C
H sp
2
H
H
All atoms lie in one Planar

plane in all conformation
H
H
C C C
H is non-planar
H
H
H
C C H
H C C
H H
Non-planar in many conformations due to rotation along.
C2 — C3 bond.
27. Which of the following molecules, in pure form, is (are) unstable at room temperature? [IIT-JEE-2012]
O
O
(1) (2) (3) (4)
Sol. Answer (2, 3)
The compound is antiaromatic and hence unstable at room temperature. The other compound
–
O O
+
is also unstable at room temperature due to partial positive charge at carbonyl C-atom
28. Among P, Q, R and S, the aromatic compound(s) is/are [IIT-JEE-2013]
Cl
AlCl3
P
NaH
Q
(NH4)2CO3
R
100-115 °C
OO
O
HCl
S
(1) P (2) Q (3) R (4) S
Sol. Answer (1, 2, 3, 4)
AlCl3
Cl AlCl4 (P)
(i)
(AROMATIC)
Na
NaH
(Q) + H2
(ii)
(AROMATIC)
(NH4)2CO3
R
(iii) 100–115ºC
O O

(NH4)2CO3 2NH3 + CO2 + H2O
 IMPE
+ NH3
O O O O NH2 O NH2 OH
H
H H H H
N N N
 IMPE
–2H2O
HO OH O OH
(R) AROMATIC
HCl
(iv) O OH Cl (S)
(AROMATIC)
29. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to [IIT-JEE-2013]
(1)   p (empty) and   electron delocalisations
(2)  * and   electron delocalisations
(3)   p (filled) and   electron delocalisations
(4) p (filled)  and   electron delocalisations
Sol. Answer (1)
In hyperconjugation   p (empty) electron delocalization for tert-butyl carbocation and   * electron
delocalization for 2-butene will take place.
30. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are
[JEE(Advanced)-2014]
(1) Tert-butanol and 2-methylpropan-2-ol
(2) Tert-butanol and 1, 1-dimethylethan-1-ol
(3) n-butanol and butan-1-ol
(4) Isobutyl alcohol and 2-methylpropan-1-ol

Common name IUPAC name
OH
(1) tert-butanol 2-methylpropanol
(3) OH n-butanol butan-1-ol
(4) OH isobutyl alcohol 2-methyl propan-1-ol
31. The IUPAC name(s) of the following compound is(are) [JEE(Advanced)-2017]
H3C Cl
(1) 1-chloro-4-methylbenzene (2) 4-chlorotoluene

(3) 4-methylchlorobenzene (4) 1-methyl-4-chlorobenzene
Sol. Answer (1, 2)
IUPAC name
Cl CH3
1 1
2 2
(1) (2) 4-chlorotoluene
1-chloro-4-methylbenzene 3
3
4 4
CH3 Cl
SECTION - C
Linked Comprehension Type Questions
Comprehension-I
Tautomerism, strictly defined could be used to describe the reversible interconversion of isomers. Interconversion
of isomers is due to mobility of an atom or a group.
R R
R—HC—C O R—CH C—O
H H
In the above examples the composition of the equilibrium mixture is of course, governed by the relative
thermodynamic stability of the two forms under the particular conditions being studied.
1. In which of the following tautomeric equilibrium concentration of right hand product is more than left hand
product?
H
O O
O O CH3 O
(1) CH3—N CH2—N (2)
O O—H H3C O H2C OH
O OH O
O OH O
(3) (4) C
EtO OEt EtO OEt
Sol. Answer (3)
In dienone phenol tautomerism phenol form is more stable due to its aromatic character.
O O
H
H
More stable
2. In which of the following solvent percentage enol content is maximum for 2,4-pentanedione?
(1) CH3CN (2) H2O (3) n-Hexane (4) Ethanol
Sol. Answer (3)
In non-polar solvent enol content would be maximum
Comprehension-II
Names of organic compounds are under the latest guide line of IUPAC. IUPAC means international union of
pure and applied chemistry. The main rules are longest chain rule, lowest number rule etc. We have to include
the rules for naming the substituents, multiple bonds and even functional groups.
1. Write the IUPAC name of the following compound
CN
CN
(1) 3,3-Diethenyl pentane1,5-dinitrile (2) 3,ethenyl,3-ethyl pentane 1,5-dinitrile
(3) 3,3-diethenyl pentane 1,5-dicyanide (4) None of these
Sol. Answer (1)
(4)
(5)
CN
(3)
(2)
CN
(1)
OH
2. , IUPAC name is
OH
(1) 3,3-diethenyl pentane 1,5-diol (2) 2,2-diethenyl propane 1,3-diol
(3) 2, 3-diethenyl propane 1,3-diol (4) 3,3-diethenyl propane 1,3-dialcohol
Sol. Answer (2)
(3)
(2) OH
(1)
OH
3. Write IUPAC name of

3
4 2
1
5
6 4
3
1 2
(1) 5-(3,3-dimethyl cyclobutyl) 1,2,2,3-tetra ethyl cyclohexane

(2) 5-(3,3-dimethyl cyclobutyl) 1,3-diethyl 2,2-dimethyl cyclohexane
(3) 1,2,2,3-tetra ethyl 5-(3,3-dimethyl cyclobutyl) cyclohexane
(4) None of these
Sol. Answer (1)
Fact
Comprehension-III
Weak Acid does not dissociate completely into its ions. It is in equilibrium with its conjugate base. Greater is the
K
stability of conjugate base, greater is value of k for that equilibrium making the equilibrium move in (HA a H++A–)
forward direction. i.e., more is the degree of dissociation of that acid. Same is the case for weak bases. Factors
affecting the stability of conjugate acid or base are electronic effect like resonance effect and inductive effect acting
upon the species.
1. Which of the following is strongest acid?
OH OH OH OH
CH3
(1) (2) (3) (4)
CH3
CH3
Sol. Answer (1)
Alkyl group (electron donor) decreases acidic strength of phenol
2. Which of the following is having most acidic -Hydrogen?
O
(1) CH3—NO2 (2) CH2 NO2 (3) NO2 CH NO2 (4)
NO2 NO2
Sol. Answer (3) O
H
Conjugate base of O2N C NO2 is
NO2
Stabilized by three strong electron withdrawing groups

i.e., O O

N C N
O O
N
O O
Stabilized by –I and –M effect of three –NO2 groups
3. Which of the following is most basic due to +R effect of any substituent?
NH2 NH2
..
(1) N (2) .. (3) (4)
N OCH3
H
CH3 OCH3
Sol. Answer (4)
+R effect of –OCH3 predominates over –I effect
Comprehension-IV
Hyperconjugation is defined as No bond resonance. The concept of hyperconjugation arose from the discovery
of electron releasing pattern for alkyl groups. It involves  electrons of C–H bond. Greater the number of C–H
bond (  -hydrogen atom w.r.t. double bond) more will be hyperconjugative structures, more will be stability. Heat
of hydrogenation of alkene are affected by hyperconjugative effects.
1. Which of the following is incorrect hyperconjugative structure?
H H H H
H C H H C H H C H H C H
(1) (2) (3) (4)
Sol. Answer (3)

H is released as H+ not as H–
2. Which of the following has highest magnitude of enthalpy of hydrogenation?
(1) (2) (3) (4)
Sol. Answer (1)

Hydrocarbon (1) is least stable, as it is not stabilized by resonance, and has lesser number of hyper
conjugative structures.
SECTION - D
Assertion-Reason Type Questions
1. STATEMENT-1 : In naphthalene all C—C bonds are equal.
Naphthalene
and
STATEMENT-2 : Like benzene naphthalene is also aromatic.
Sol. Answer (4)
More contributing Less contributing
 All C—C bonds are not equal.
2. STATEMENT-1 : p-Nitroaniline is more polar than nitrobenzene.

and
STATEMENT-2 : Nitro group has – M effect.
Sol. Answer (2)
Both statements are correct but reason for this is combined effect of –NO2 and –NH2.
3. STATEMENT-1 : All C—C bonds are equal in [10]-Annulene.

and
STATEMENT-2 : [10]-Annulene is a non-aromatic compound.
Sol. Answer (4)
All C—C bonds are not equal in [10]-Annulene.
HO O OH
4. STATEMENT-1 : is less acidic than

HO
O
Squaric acid Phenol
and
STATEMENT-2 : Conjugate base of phenol is resonance stabilized.
Sol. Answer (4)
Infact squaric acid is more acidic than phenol.
Br
5. STATEMENT-1 : When is treated with excess of Ag+ ion. One mole of the compound reacts
Br
Br
Br
(X)
with four moles of Ag+.

and
STATEMENT-2 : Ag+ is a Lewis acid hence it reacts with Br– ion on which is a Lewis base.
Sol. Answer (4)
Compound (X) will give only two moles of AgBr.
6. STATEMENT-1 : A compound with odd number of nitrogen always contains odd molecular weight.
and
STATEMENT-2 : Nitrogen has odd molecular mass.
Sol. Answer (3)
Molecular mass of nitrogen is 14.
7. STATEMENT-1 : Aldehydes and ketones having same molecular formulae are structural isomers.
and
STATEMENT-2 : Aldehydes and ketones are metamers.
Sol. Answer (3)
Aldehydes and ketones cannot be metamers.
8. STATEMENT-1 : Carbocationic rearrangement is known as electrophilic rearrangement.
and
STATEMENT-2 : Carbocations are stabilized by both hyperconjugation and +I effect.
Sol. Answer (4)
Carbocationic rearrangement is known as nucleophilic rearrangement.
9. STATEMENT-1 : Cyclopentanone exhibits keto-enol tautomerism.

and
STATEMENT-2 : Cyclopentanone has two hydrogen atoms attached to the carbon atom adjacent to carbonyl
group.
Sol. Answer (1)
O OH
Tautomers
10. STATEMENT-1 : CH3 CH2 CH2 is less stable than CH3 – N – CH2
|
H
and
STATEMENT-2 : Carbocation with adjacent hetero-atom like N, O are less stable.
Sol. Answer (3)
If ‘N’ or ‘O’ are attached to carbocation. These groups participate in the delocalization of +ve charge.
11. STATEMENT-1 : Cyclopropane is more stable than cyclobutane.

and
STATEMENT-2 : Angle strain in cyclopropane is higher than cyclobutane.
Sol. Answer (4)
1
Angle strain  of cyclic compound.
stability
O
||
12. STATEMENT-1 : Keto form is less stable than enol form.
O
||
and
STATEMENT-2 : Enol form is stabilized by aromaticity.
Sol. Answer (1)
O OH
O
OH
13. STATEMENT-1 : Aniline undergoes Friedel-Craft alkylation more readily than Toluene.
and
STATEMENT-2 : Aniline undergoes fast electrophilic substitution than Toluene.
Sol. Answer (4)
Aniline does not follow Friedel-Craft reaction.
14. STATEMENT-1 : Bridge head carbocation is less stable than Bridge head carbanion.
and
STATEMENT-2 : C atom in carbocation is sp2 generally hybridized.
Sol. Answer (2)
Carbocation and carbanion are generally sp2 and sp3 hybridised
SECTION - E
Matrix-Match Type Questions
1. Match the following
Column-I Column-II
(Molecular formula) (Type of isomerism)
(A) C6H12O (p) Functional isomerism
(B) C4H11N (q) Geometrical isomerism
(C) C6H12 (r) Metamerism
(D) C5H12O (s) Tautomerism
(t) Position isomerism

Sol. Answer A(p, q, r, s, t), B(p, r, t), C(q, t), D(p, r, t)
C6H12O has one degree of unsaturation.
 Carbonyl compounds, unsaturated alcohols and ethers are possible. This can also exhibit geometrical
isomerism
C4H11N can form 1°, 2° & 3° amines which are functional isomer.

Column-I Column-II
(Estimation) (Method)
(A) C (p) Liebig method
(B) H (q) Duma method
(C) N (r) Kjeldahl's method
(D) X (Chalcogen) (s) Carius method

Sol. Answer A(p), B(p), C(q, r), D(s)
Factual based
Column-I Column-II
(Estimation) (Percentage)
(A) 0.45 gm organic compound gives 1.1 gm (p) 66.6% C
CO2 and 0.3 gm H2O 7.4% H
(B) C : H : N ratio in compound 18 : 2 : 7 (q) 26% N
(C) 0.37 gm of a given compound gave 0.631 gm AgBr (r) Equivalent mass of acid is 122
(D) 0.122 gm of an organic acid required (s) 72.6% Br
N
10 cm3 NaOH for neutralisation
10
Sol. Answer A(p), B(p, q), C(s), D(s)
12 Mass of CO2
(A) Percentage of C = 44  Mass of organic compound  100
12 1.10
   100  66.6%
44 0.45
2 Mass of H2 O
Percentage of H = 18  Mass of compound  100
2 0.3
   100  7.4%
18 0.45
18
(B) Percentage of C =  100  66.66%
27
2
Percentage of H =  100  7.40%
27
7
Percentage of N =  100  26%
27
80 Mass of AgBr
(C) Percentage of Br = 188  Mass of compound  100
80 0.631
  100  72.6
188 0.37
N
(D) 10 cm3 of alkali required acid = 0.122 g
10
0.122
1000 cm3 of 1 N alkali required acid =  1000  10
10
= 122 g
But 1000 cm3 of 1 N alkali contain 1 gm equivalent of the alkali which must react with 1 gm equivalent
of acid.
 Equivalent weight of acid = 122
4. Match the carbocation in column-I with the effect which is major, stabilizing factor for it in column-II
Column-I Column-II
(A) Carbocation (p) Nucleophile
(B) Carbanion (q) Electrophile
(C) Free radical (r) Stabilized by +I effect
(D) Carbene (s) Stabilized by resonance
Sol. Answer A(q, r, s), B(p, s), C(r, s), D(p, q, s)

Carbocation is electrophile and stabilised by +I effect resonance and hyperconjugation.
Carbanion is nucleophiles and stabilized by resonance and –I effect
Free radical is electrophile and stabilised by resonance and hyperconjugation.
Carbene can act as electrophile and nucleophile both.
5. Match the carbocation in column-I with the effect which is major, stabilizing factor for it in column-II
Column-I Column-II
(A) (p) Aromatic character
(B) CH3 — CH (q) Resonance

CH3
(C) (r) Hyperconjugation
(D) CH3 — O — CH2 (s) Inductive effect

Sol. Answer A(q), B(r, s), C(p, q), D(q, s)
is resonance stabilised but antiaromatic
+
CH3 CH has 6 –H for hyperconjugation and 2 methyl groups for + I effect
CH3
+
is aromatic resonance stabilised cation
 
CH3 –O– CH2 is resonance stabilised because it can form CH3 – O  CH2
Column-I Column-II
+
(A) (p) Resonance stabilisation
O
(B) (q) Aromatic molecule
CH3
(C) (r) Hyperconjugation effect is observed
(D) CH3 – CH = CH – CH = CH2 (s) At least one carbon is sp2 hybridised

(t) Achiral compound
Sol. Answer A(p, r, s, t), B(p, q, s, t), C(p, q, r, s, t), D(p, r, s, t)
Resonance is possible in A and B. B and C are aromatic. (C) and (D) have hyperconjugation effect due to
-hydrogen.
7. Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II.
[IIT-JEE-2008]
Column I Column II

(A) H2N—NH3Cl (p) Sodium fusion extract of the compound gives Prussian blue
colour with FeSO4

NH3l
(B) HO (q) Gives positive FeCI3 test
COOH

(C) HO NH3Cl (r) Gives white precipitate with AgNO3

(D) O2N NH—NH3Br (s) Reacts with aldehydes to form the corresponding
NO2
hydrazone derivative
Sol. Answer A(r, s); B(p, q); C(p, q, r), D(p)
SECTION - F
Integer Answer Type Questions
1. One mole of a compound with molecular formula C30H43N absorbs 8 moles of H2 gas under catalytic
hydrogenation. Then what is the ratio of number of  bonds to the number of rings in the compound?
Sol. Answer (4)
43  1
Degrees of unsaturation in the compound = 31  = 31 – 21 = 10
2
 Out of which 8  bonds are present
 bond 8
Hence  4
ring 2
2.
How many intermediates are possible (excluding stereoisomer) when above mentioned molecule is attacked
by 1 equivalent H+?
Sol. Answer (6)
3. On how many atoms positive charge is delocalized in the given ion?
Sol. Answer (4)
F F F F
Hence positive charge is delocalized over four atoms.
4. How many of the given species will behave as an electrophile?
CCl2, NH3, CH3, NH 4, CH 3, OH, BF3, AlCl3, Br

Sol. Answer (5)
–
NH3, NH4, CH3 and OH are not electrophiles, infact they are nucleophiles
5. How many bicyclic isomers are possible for the molecular formula C6H12O?
Sol. Answer (0)
Index of hydrogen deficiency is 1.
 Bicyclic system is not possible for this.
6. How many of the given species will evolve CO2 with NaHCO3?
OH OH OH
HO O O CH CH2
O2N NO2 O OH OH
, , , , H
,
O
HO HO OH
NO2
O O OH OH
NO2 NO2
, , , ,
O
O NO2
Sol. Answers (3)
Trinitrophenol, squaric acid and Vth product can give CO2 with NaHCO3.
7. How many total types of products are formed by dehydrohalogenation of 2-chlorobutane?

Sol. Answer (3)
1-Butene, Cis-2-butene,trans-2-butene
8. The total number of structural dihaloderivatives possible in n-pentane are ____.
Sol. Answer (9)
(1, 1), (1, 2), (1, 3), (1, 4), (1, 5), (2, 2), (2, 3), (2, 4), (3, 3)
Dihaloderivatives are nine different compounds.
9. Amongst the following, the total number of compounds soluble in aqueous NaOH is [IIT-JEE-2010]
H3C CH3
N COOH OCH2CH3 OH
CH2OH
NO2 OH CH2CH3 COOH

CH2CH3
N
H3C CH3
Sol. Answer (4)

Carboxylic acids and aromatic alcohols dissolves in aqueous NaOH.
COOH OH OH COOH
, , ,
N
H3C CH3
will be soluble in aqueous NaOH.
10. The total number of contributing structures showing hyperconjugation (involving C-H bonds) for the following
carbocation is [IIT-JEE-2011]
H3C CH2CH3
+
Sol. Answer (6)
HC
3 CHCH
2 3
+
It contains 6 -hydrogen atoms.

 6 contributing structures are possible
11. The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is
[IIT-JEE-2010]
Sol. Answer (5)
Index of hydrogen deficiency in the compound C4H6 is 2. Therefore either bicyclic compound or cycloalkenes
are possible as cyclic isomers.
 Possible isomers are
, , , ,
12. The number of resonance structures for N is [JEE(Advanced)-2015]

OH
NaOH
N
Sol. Answer (9)
OH O
NaOH
–H2O
O O O O
II III IV V
O O O
III VI VII
O O
VIII IX
13. Among the following, the number of aromatic compound(s) is [JEE(Advanced)-2017]
+ + +
Sol. Answer (5)
, , , and are aromatic.

+
+
and are non-aromatic while and are antiaromatic compounds.
SECTION - G
Multiple True-False Type Questions
1. STATEMENT-1 : Phenol is more acidic than benzoic acid.
STATEMENT-2 : Fluorobenzene is less reactive than chlorobenzene towards electrophilic substitution.
STATEMENT-3 : Friedel Craft alkylation is not possible in tertiary butyl benzene.
(1) T F T (2) F F F (3) F T F (4) T T F
Sol. Answer (2)
Phenol is less acidic than benzoic acid due to less stability of C6H5O– than C6H5COO–. Fluorobenzene is
more reactive than chlorobenzene.
O
  
2. STATEMENT-1 : CH3  O  CH2 is more stable than O  N  CH2 .
STATEMENT-2 : + is antiaromatic molecule.
STATEMENT-3 : Phenoxide is more stable than ethoxide.
(1) F F T (2) T T F (3) F T F (4) T F T
Sol. Answer (4)
.. 
In CH3  O
..  CH2 , resonance is effective. + – is aromatic (10 e–). Phenoxide is resonance
stabilised.
SECTION - H
Aakash Challengers Questions
1. Rank the given species in the increasing order of water solubility?
CHO CHO OH CHO

OH HO OH OH
OHC
OH OHC HO
OH CHO CHO OH
I II III IV
Sol. Correct increasing order of water solubility would be
II < I < III < IV
Increasing solubility
in water
Greater the number of intermolecular hydrogen bond with solvent molecule higher the solubility.
2. The given six compounds are similarly sized, very similar molecular weight and number of electrons, but the
boiling point of these compounds are quite different (30°C–141°C). Rank these compounds in the increasing
order of boiling point (lowest boiling first)
OH O O NH2
N
I II III
OH
IV V VI
VI < V < IV < II < I < III

Sol.
Increasing boiling point
Strongest hydrogen bond is present in III. While weakest intermolecular force of attraction is present in VI.
3. For the given pair of compounds, identify the compound you expect to have the higher boiling point and explain
your reasoning.
N — H and NH2
Sol. NH2
To predict relative boiling points, look for differences in

(i) Hydrogen bonding
(ii) Molecular weight and surface area and
(iii) Dipole moment
4. Which of the following reactive intermediate is more stable and why?
I II
Sol. II > I
Bridge head carbocation are least stable. Because bridge head carbon cannot attain planarity.
5. Salt of Ph3C—X– can be stored for months. Explain why.
Sol. Triphenyl methyl cation is very stable, due to resonance.
+ In triphenyl methyl carbocation positive charge can be delocalized in all the 3 ring systems
C
causing the lowering of energy and making the carbocation very stable.
6. For the dehydration reaction
CH2OH CH2 CH3

H+ + +
Explain the mechanism discussing formation of all the 3 products.
Sol.
H
CH2OH CH2 O CH2
H+ H
(H2O being a rearrangement
good leaving of carbocation
group)
CH2 elimination
of H
CH3
CH3
CH2 Ring expansion

to bring release –H
from ring strain
CH2 – OH + CH2
H
Ring expansion
Hydride shift
CH3
-H elimination
7. Which of the following carbanion is less stable and why?
OCH3 OCH3
NH2
or
NH2
OCH3
NH2
Sol. is less stable, as a methoxyl group has negative (electron-withdrawing) inductive effect so
OCH3
negative charge will be less available on , making it more stable.

NH2
Hint : Electrons in both the carbanions are out of the plane of the  cloud, hence there is no resonance
interaction, only the inductive effect works.
NH2
8. Aromatic amines are weakly basic, whereas is strongly basic, explain this unusual behaviour.
Sol. Planarity between lone pair of nitrogen and  electron of ring is lost due to two bulky groups on ortho position.
9. Which of the following hydrocarbons can be readily deprotonated by NaOEt? Explain.
H; ; ;
I II III IV
Sol. Only III can be deprotonated by NaOEt as its conjugate base is aromatic.
10. Pick out the correct statements about the barrier of rotation about the indicated bond in the given compounds.
I II III IV
(1) I and IV will have nearly same barrier of rotation

(2) II and III will have nearly same barrier of rotation
(3) At room temperature I will have frozen rotation
(4) III will have relatively lower barrier of rotation as compared to IV
Sol. Answer (1, 2, 3, 4)
In II and III charge separated structures are more contributing.
11. Arrange the given species in the increasing acidic strength :
I II III IV
(1) II < I < IV < III (2) IV < III < I < II (3) II < I < III < IV (4) III < IV < II < I
Sol. Answer (3)
Stronger acids have more stable conjugate base.
–H
Least acidic
Lesser delocalization
of negative charge,
hence least stable
12. Order of basicity of the following species is
N N
N N
N
N
H N N
H
I II III IV
(1) I > II > IV > III (2) III > IV > II > I (3) IV > III > I > II (4) II > I > III > IV
Sol. Answer (4)
Conjugate acids of I and II are stabilized by resonance.
13. The correct stability order of the following resonance structures is
OMe O—Me
Me Me
N N CH2
Me CH2 Me
(I) (II)
O—Me OMe
Me Me
N CH2 N CH2
Me Me
(IV) (III)
(1) I < III < IV < II (2) I < IV < III < II (3) I < IV < II < III (4) IV < I < II < III
Sol. Answer (3)
More number of covalent bonds more contributing structures.
14. What would be the major product of the given reaction? Justify mechanistically for the formation of your product?
H2SO4

CH2—OH
Sol. Alcohols in the presence of H+ will result into formation of carbocation which will result into the formation of
more stable carbocation.
15. Write mechanism for the following transformation
HNO3
NO2
Sol. HNO3 generates NO 2 ion through self ionization which attacks on aromatic ring to give the desired product.
16. Correct statements among the following is/are
D D D D
(1) and are identical compounds
D D D D
(2) and are structural isomers
D D
D D
(3) and are identical compounds
D D
D D
(4) and are structural isomers
Sol. Answer (2, 3)
is anti-aromatic while is aromatic.
17. Species in which all C—C bonds are not equal is/are
(1) (2) (3) (4)

(1) is anti-aromatic while (3) and (4) are non-aromatic. Therefore in these molecules less effective -
electron delocalization will occur and hence all C—C bonds will not be equal.
18. Consider the following equilibrium between two conformers of methyl cyclohexane
Me
Keq
Me
Me at axial Me at equatorial
position position
What is the percentage of axial conformer if the equilibrium constant for the given equilibrium is 18?
Sol. Answer (5)
[Equatorial conformer] 18
K 
[Axial conformer] 1
[Equatorial conformer] 18
Percentage equatorial conformer   100   100 = 95%
[Equatorial]  [Axial conformer] 18 1
Percentage axial conformer = 5%
19. Most stable carbocation among the following is
(1) (2) (3) (4)
I II
III IV
Sol. Answer (2)

Maximum delocalization of positive charge occur in II.
20. For which of the following compound tautomerization reaction is very slow?
O—H O O—H O
(1) C C (2) C C
F2C CH3 HF2C CH3 H2C CH3 H3C CH3
O O
(3) (4)
H
O O
O O
Sol. Answer (1) H
In case of highly fluorinated enols the enol form is less stable than keto form. Yet enol form can be kept at
room temperature for long periods of time because the tautomerization reaction is very slow.
21. Aromatic species among the following is/are
(1) (2) (3) B—R (4)
Sol. Answer (3, 4)

Both are planar and contain 6 & 14 e– respectively.
22. A solution of the sodium salt of diphenyl methane, Ph2CHNa in diethyl ether is orange, due to absorption of
light in the blue region by the delocalized diphenyl methide ion, when colorless triphenyl methane is added,
the color changes to red. Explain this result. Would you expect the addition of diphenyl methane to the sodium
salt of triphenyl methane, in diethyl ether to result in a change in color from red to orange? Give explanation.

Sol. Ph2CHNa  Ph3 CH
Ph2 CH2  Ph3 CNa
23. Consider the following tautomeric equilibrium

Me Me
H
Et3N 50%
D2O 50%
H H
H
Correct statement about the above equilibrium is
(1) This interconversion is an intermolecular process (2) It is an intramolecular process
(3) Interconversion involves carbanion intermediate (4) Interconversion involves carbocation intermediate
Sol. Answer (2)
In the given example neither carbanion is formed nor carbocations is formed.
24. Most stable and least stable species respectively among the following are
O
O O
S S
S O S S
O O
O O
I II III IV
(1) II and I (2) IV and II (3) III and II (4) II and IV

Sol. Answer (4)
Maximum delocalization of negative charge is taking place in II. Electro negativity of S is less than oxygen.
25. Compare acidic strength of
O O O O
NH3 H—C CH3—S—OH
O—H HH
O
I II III IV
(1) II > I > III > IV (2) IV > II > I > III (3) III > IV > II > I (4) II > IV > I > III
Sol. Answer (2)
IV > II > I > III
Decreasing acidic strength
pKa these acids are

Acid pKa
I 5
II 3.5
III 10
IV 1
26. Which of the following species can be used as antioxidant?
(Note : Antioxidants have capability to trap free radicals)
CH—CH2 OH OH
O
O
OH OH
(1) (2) H (3) (4)
HO OH
Except naphthalene all three compounds can trap free radicals due to presence of oxygen.


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Chapter 12

Organic Chemistry : Some Basic

Structure, Classification, Nomenclature of Organic Compounds

(1) 3-diisopropyl-2,4-dimethylpentane (2) 2, 4-dimethyl-3-diisopropylbutane

2. The IUPAC name of the compound

4. Which will have the highest melting point?

(1) (2) (3) (4)

7. What is the index of hydrogen deficiency in the molecule C12H17NO?

8. Which of the following compound cannot have a  bond?

9. Which of the following compounds will have highest enolic content?

(1) (2) CH3COCH2CHO (3) CH3CHO (4) CH3COCH3

Sol. Answer (1)

mos t stable enol

10. The total number of structural monochloroderivatives possible in C5H12 is

Electronic displacement, Resonance, Aromaticity

12. At conjugated position – NO imparts

13. In the given anion, –ve charge is delocalized on

Sol. Answer (2)

CH3 CH3 CH3 CH3 CH3 CH3

CH3 CH3 CH3 CH3 CH3 CH3

17. Among the following, the most stable carbocation is

Sol. Answer (2)

18. Resonance is not possible in

(1) (2) NH3 (3) NO2 (4) BH2

19. Which of the following hydrocarbon is most acidic?

(1) (2) (3) (4)

Sol. Answer (1)

is most acidic because it generates most stable aromatic conjugate base.

22. The number of sp2 hybridised carbon in one benzyne is

. All carbon atoms are sp2 hybridised.

Sol. Answer (4)

24. Strongest and weakest acid among the following is

Sol. Answer (4)

25. Correct order of acidic strength for the given species

CH3—C N—H CH3—CH2—CH3 CH3—C C—H CH2—H

Sol. Answer (3)

28. Most acidic species among the following is

29. Which of the following is the strongest base in water?

(1) (2) NH2 (3) (4)

Sol. Answer (4)

Sol. Answer (2)

31. Most acidic species among the following is

33. Which of the following reactions will not generate a carbanion?

35. Which of the following species cannot behave as electrophile?

36. Least stable carbocation among the following is

(1) (2) (3) CH3 – C – CH3 (4) CH

(1) (2) (3) (4)

Sol. Answer (2)

39. Among the following,

40. Correct stability order of the given free radicals is

Sol. Answer (2)

41. In which of the following homolytic bond fission takes place?

⎡ Purification, Separation, Quantitative and ⎤

(1) (NH2)2 C O (2) H2N (C6H4) SO3H (3) C6H5SO3H (4)

Sol. Answer (2)

(1) NH2 (2) N N

Sol. Answer (2)

Sol. Answer (1)

48. Hyperconjugation involves overlap of the following orbitals [IIT-JEE-2008]

50. The correct acidity order of the following is [IIT-JEE-2009]

> > >

51. The IUPAC name of the following compound is [IIT-JEE-2009]

HO H CH3 :OH H CH3