GOCSHEET2021

CONTENT
S.No Pages
1. Theory 04 – 35
2. EXERCISE - 1 36 – 39
3. EXERCISE - 2 [Level - 1] 40 – 44
4. EXERCISE - 2 [Level - 2] 45 – 57
5. EXERCISE - 3 58 – 65
6. EXERCISE - 4 [Level - 1] 66 – 71
7. EXERCISE - 4 [Level - 2] 72 – 75
8. ANSWER KEY 76 – 78
9. SOLUTION 79 – 144
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HOMOLYTIC BOND FISSION HOMOLYSIS
The bond cleavage in which each bonded atom gets their own contribution
A – B  A  B
or
Free Radical
A
B
• Cleavage takes place due to

HELP (H = Heat, E = Electricity,
L = light, P = Peroxide)
• Favoured when E.N. difference is less or zero.
• Cleavage favoured in non polar solvent.
HETROLYTIC BOND FISSION
– +
C + A (C is more electronegative)
(Carbanion)
C A
+ –
C + A
(A is more
electronegative)
(Carbocation or
carbonium ion)
• It is formed when the electronegativity difference between the bonded atoms is more
• formation is favoured by polar solvent
 –  –
C A .............. H – O
|
Attraction 
H
+ve charge of the solvent attracts the –ve pole of compound and the –ve pole of the solvent attracts +ve pole of
compound and the bond breaks.
INTERMEDIATES OF ORGANIC COMPOUNDS

Free Radical Carbocation Carbanion
(1) Lone pair 0 0 1
(2) Bond pair 3 3 3
(3) Unpaired e– 1 × ×
(4) Bond Angle 120º 120º 107º
(5) Hybridisation sp2 sp2 sp3
(6) Shape Trigonal planer Trigonal planer Pyramidal
(7) Magnetic property Paramagnetic Diamagnetic Diamagnetic
(8) Stability order 3º > 2º > 1º 3º > 2º > 1º 1º > 2º > 3º
(As per inductive effect)
(9) e– rich/deficient/poor ED(Deficient) ED ER(Rich)
(10) Reactivity order 1º > 2º > 3º 1º > 2º > 3º 3º > 2º > 1º
(11) +I/–I (stablized) +I +I –I
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ELECTRONIC DISPLACEMENT EFFECT

The displacement of electrons within the same molecule is known as electronic displacement. These effects
affect the stability of a species or compound and it also affect the acidic & basic strength.
Electronic Displacement Effect is divided into two parts:
(1) Permanent effect
(2) Temporary effect
(1) Permanent effect :

(i) Inductive effect
(ii) Mesomeric (resonance) effect
(iii) Hyperconjugation
(2) Temporary effect:
(i) Electromeric effect
(ii) Inductomeric effect
(i) Inductive effect:
It is an effect in which permanent polarisation arises due to partial displacement of -electrons along carbon
chain or partial displacement of sigma-bonded electron toward more electronegative atom in carbon chain.
C – C – C – Cl
Magnitude of partial positive charge
– (net charge remain constant in a molecule having inductive effect)
Inductive effect
It is a permanent effect
         –
C C C C C X (–I effect of X)
5 4 3 2 1
if X i.e more electronegative

(After carbon No. 3 the effect disappears)
(+ I effect of Y)
+ +
H–N–H R–N–R
* | < | (– I effect order)
H R
* O– < O < O+ (–I effect order)

• It is a permanent effect
• It is caused due to electronegative difference.
• It operates via  bonded electron.
• It is distance dependent effect.
• As distance increases, its effect decreases.
• It can be neglected after third carbon.
• It is a destablising effect.
• It is divided into 2 parts. (On the basis of electronegativity w.r.t. hydrogen atom)
(1) +I effect (2) – I effect
If any atom or group having electronegativity greater than that of hydrogen. than it is considered as – I effect and
vice-versa.
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+I effect
(i) e– releasing group
(ii) EN less than H
(iii) Those group which are showing + I effect, disperses partial – ve charge on the C-chain
– I effect
(i) e– accepting group
(ii) EN greater than H
(iii) Those group showing –I effect disperses + ve charge on the C-chain
Eg. CH3 – CH2 – Cl (–I of Cl)
Eg. CH3 – CH = CH2 (–I of –CH=CH2 & +I of –CH3)
Eg. CH3 – CH2 – C  CH (–I of –C  CH & + I of –CH2–CH3)
Eg. I – Cl
+I –I
Eg. CH2 = CH (–I of –ph)
Order of –I effect showing group:
O
– NF3 >– NR3 >– NH3 >–NO2 >–CN >–C–H
O O
> –C–R > –C–OH > –F > –Cl >–Br>–I
(–I order) – C  CH > – CH = CH2

Order of + I effect showing group
– CH2 > – NH > – O > – CMe3 > – CHMe2
> – CH2Me > CT3 > CD3 > CH3 > T > D > H
Bond Strength : CT3 > CD3 > CH3 (+ I of T > D > H)

Q. Why carbon - hydrogen bond is longer than C - T bond
Ans As the mass increases, vibration decreases as a result of which the heavier isotope will be more closer to the C-
atom for a longer time. Therefore C – T bond is stronger C – T > C – D > C – H
Which implies that C – H bond has longest bond
APPLICATION OF INDUCTIVE EFFECT

To compare the stability of intermediates.
Intermediates
These are real separable species having measurable stability formed during coversion of reactant to product.
(After bond cleavage and before bond formation).
6 types of intermediates:
(i) Free radical (ii) Carbocation
(iii) Carbanion (iv) Carbene (v) Nitrene (vi) Benzyne
They are formed by homolytical and heterolytical cleavage.
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MESOMERIC EFFECT (RESONANCE EFFECT)

Delocalisation of  electrons in any conjugated system is known as mesomeric effect
Types
1 + M effect (+R)
2 – M Effect (–R)
* Consider the following conjugated system
H2 C = CH – CH = CH – Y CH2 – CH = CH – CH = Y+
(+M effect of y)
* Consider another conjugated system
O–
+
C=C–C=C–N=O C–C=C–C=N
O
O
(– M effect of NO ) 2
MESOMERIC EFFECT IN PHENOL (+ M EFFECT)
+ + +
OH O–H O–H O–H O–H
– –
+M effect in aniline
+ + +
NH2 NH2 NH2 NH2 NH2
– –
If the movement of e– is towards ring  (+M effect)

This effect increases the electron density over benzene ring.
* –M effect in Benzaldehyde
H–C=O H – C – O– H – C – O– H – C – O– H – C = O
+ +
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SOLVED EXAMPLE
EXAMPLE 1
Idenfity the compound showing +M or –M seperately
O
OH – C = O SH
OH – S = O
(a) (b) (c)
SOLUTION
(a) (–M) (b) (–M) (c) +M
* +M group increases electron density of ring while – M decreases the electron density of benzene ring.
* if NO2 is present on the ortho or para position then along with its –I effect, It will also show –M effect.
+ + +
OH O–H O–H O–H
–
N=O N=O N=O N–O
O O O O
(–M)
* Above compound have +M of –OH and –M of NO2 group.
+ +
OH O–H O–H
–
O –
=
N N=O
N=O
O
O O
as we can easily see that –NO2 at meta position is not attracting e– density towards it self and that's why it will not
show –M effect at m-position
RESONANCE
Delocalisation of -electrons in conjugation is known as resonance.
(Actual Structure)
(resonating structures) (Resonance hybrid)
in this form
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CONDITION FOR SHOWING RESONANCE

1. Molecule should be planer, nearly planer or a part of it is planar
Q.1 Which are planer
(A) (B) *(C) *(D)
Because all carbon atoms are sp2 hybridised.

2. Molecule should have conjugated system.
Conjugated System :
Continuous unhybridised p-orbital parallel to each–other.
Types of Conjugated System:
(1) -bond alternate to -bond
CH2 = CH – CH = CH2
(2) -bond alternate to + charge

CH2 = CH – CH2+
+
Eg. CH 2 = CH – CH = CH2
CH2 – CH = CH – CH2
R.S. CH2 CH CH CH2
CH2 – CH = CH – CH2
+ _ _ +
Eg. CH2 = CH – CH2
CH2 – CH = CH2 CH2 CH CH2
Eg. CH2 = CH – CH2
CH2 – CH = CH2
CH2 CH CH2
(4) CH2 = CH – NH2 CH2 – CH = NH2
(5) CH 2 = CH – CH2
H + H
(6) CH2 = CH – BH2 B B
H H
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CH 2 = CH – C CH
(7)
CH 2 – CH = C = CH
1. Resonance takes place due to delocalization of e–.

(a) Resonance (b) Resonance absent
(c) Resonance (d) Resonance
2. Position of the atoms remains the same, only delocalization of e– takes place.
O OH
Note:– CH3 – C – NH2 CH3 – C = NH
[They are not resonating structure rather they are tautomer]
3. Bond pair get converted into lone pair and l.p. get converted into b.p.
CH 2 = C – NH 2 CH2 – C = NH2
4. In Resonance No. of unpaired e– remains the same

CH2=CH–CH=CH2 CH2 – CH = CH – CH2
(They are not resonating structure)
Resonating Structure :
(1) Hypothetical strtucture exist on paper
(2) The energy difference b/w different resonating structure is very small.
(3) All R. S. contribute twoards the formation of resonance hybrid (Their contribution may different)
(4) A single R. S. Can't explain each & every property of that particular compound
Draw The Resonating Structures : –
CH2 = CH – CH= CH – NH2

Q.1
CH2 – CH = CH – CH = NH2
O O O O O
N O N N
O O O
N N O
–m of NO2 group
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Resonance Hybrid : –
It is a real structure which explain all the properties of a compound, formed by the contribution of different R. S..
It has got maximum stability as compared R. S.
Resonance Energy : –
It is the diffrence b/w theoretical value of H.O.H & experimental value.
Or
It is the difference b/w more stable R.S. & R. H.
* More the resonance energy, more stable will be the molecule.
* Cyclohexane is thermodynamically more stable than benzene, even though resonance energy of benzene is more.
* Resoance energy is a absolute term.
CONTRIBUTION OF DIFFERENT R. S. TOWARDS RESONANCE HYBRID
(1) Non-polar R. S. contribute more than polar R. S.
(a) CH2 = CH – CH = CH2
(b) CH2–CH = CH – CH2
(c) CH2 – CH = CH – CH2
a>b=c stability
(2) Polar R. S. with complete octet will contribute more as compared with the one with incomplete octet
CH3 – CH+ – OCH3  CH3 – CH = :O+ – CH3
Incomplete octet Complete octet
(3) In polar R. S. The –ve charge should be on more electro – ve atom & +ve charge should be on more electro + ve
atom
O O
(a) CH – C – CH CH2 = C – CH3 (more stable )
2 3
O O
(b) CH2 – C – CH3 CH2 = C – CH3
(4) Compound with more covalent bond will contribute more

(5) Unlike charges should be closer to each other whereas like charges should be isotated.
(6) Extended conjugation contribute more than cross conjugation.
<
Cross conjugation < Extended conjugation

Fries Rule :–
Compound with more benzenoid structure are more stable as their Resonance energy is greater than those in
which lesser no. of benzenoid structure are present.
R. E. is <
* If double bond is participating in resonance then it will aquire partial single bond character as a result of which
bond length increase & bond strength decreases.
If a single bond is involved in resonance then it will aquire partial doulbe bond character. As a result of which bond
length decreases & bond strength increase.
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+ +
OH O–H O–H
–
Q.1
–
(a) (b) (c)
+
O–H O–H
(d) (e)
a=e>b=d>c
Q.2 (a) CH2 = N = N
(b) CH2 – N N
(c) CH2 – N = N (incomplete)
(d) CH – N = N (incomplete)
2
a>b>c>d
Cl F
Q.3 H–C Cl H–C F
Cl F
– –
–H –H
Cl F
Stability C Cl < C F
Cl F
(back bonding)
Q.4 (a) CH2 = CH – F

(b) CH2 – CH = F+ a > b (stability)
2 N N N
sp -N
H H H
N N N
H H H
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Note :
When lone pair as well as double bond is present on some atom. Then only  bond will participating resonance.
Where as lone pair remains sp2 hybridised orbital.
When an atom has two or more then two lone pair then only one lone pair will participate in resonance and the
other one remains in sp2 hybridised orbital.
HYPER CONJUGATION
Permanent polarisation caused by delocalisation of -electrons into -molecular orbital is known as
hyperconjugation
H H
|
H – C – CH2 H–C CH2
| |
H H
Hyper conjugation is called No bond Resonance
* More  C – H bond, more will be the no bond resonating structure (Hyper conjugation)
• More  (C – H) bond, more will be the stability of free radical.
(CH3)3C > (CH3)2CH > CH3 – CH2 > CH3

9  (C – H) 6  (C – H) 3  (C – H) 0
Stability order
Properties of Free Radical

1. It is a neutral species.
2. It has one upaired electron that's why paramagnetic in nature.
Structure :

C H3  methyl free Radical

C H3 CH2  ethyl free radical
3. its hydridisation is sp2 and triangular planer shape.
Note :
unpaired electron is not counted while calculating the hybridisation state.
H H
(unpaired electron stay perpendicular to the plane)

Stability of free Radical :
Its stability can be determined with the help of hyperconjugation as well as Resonance effect
ALLYLIC FREE RADICAL
CH2 = CH – CH2 CH2 – CH = CH2

(Homolysis)
(Free Radical is on next carbon to doubly bonded carbon atoms) Effect of Resonance > Hyper conjugation
CH2 – CH = CH2 > (CH3)3C

(stability)
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BENZYLIC FREE RADICAL
CH2 CH2 CH2
CH2
CH2
(5 Resonating structure)
* More Resonating structure, more will be the stability of the free Radical.
CH
(di-benzylic free Radical)

No. of Resonating structure = 7
(Tri-benzylic free Radical) No. of Resonating structure = 10

Stability Order :
   
Ph 3 C  Ph 2 C H  Ph C H 2  CH 2  CH – C H 2 
   
(CH 3 )3 C  (CH 3 ) 2 C H  CH 3 – C H 2  C H 3
EXAMPLE 2
Compare the stability of the following free Radical.
 
(a) CH3 – C H2 (b) CH2  C H (c) CH  C H
SOLUTION

(a) CH3 – C H2 will be most stable due to hyper conjugation.
 
Between CH2  C H and CH  C
sp
 more s-character
 more electronegative
 e– density maximum
 more repulsion  less stable
Ans. a>b>c
* More repulsion, less stability
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EXAMPLE 3
Compare the stability of the following free Radicals
Tending 
(a) to sp due (b) CH  C H
to allylic
structure sp2
(very unstable)

CH  C
(c) actual sp
 More repulsion  less stability
(Therefore this resonating structure is not possible)

SOLUTION b>a>c
EXAMPLE 4
*   
(a) CH3 – CH – CH3 (b) CH3 – C H2 – CH3 (c) CH3 – C H3 (d) C H4
|
CH3

Compare the C– H bond energy of the above compounds.
SOLUTION
After forming free radical from the compound
   
CH 3 – C – CH 3 CH 3 – C H – CH 3 CH3 – C H2 C H3
|
CH 3
(3°) (2°) (1°) methyl free radical

(a) (b) (c) (d)
(most stable)

therefore will have more
tendency to come in this form

And C – H bond will break very readily  bond energies will be very less.
a < b < c < d < (bond energies order)
1
* Bond energy 
stability of free Radical
* Bond length  stability of free Radical
GOC
EXAMPLE 5
Compare the potential energy of the following compounds (above compounds)
SOLUTION
If compound after being in free Radical form is very stable (i.e., less energy) it mean it would have possessed
more energy initially i.e. it potential energy will be most
a<b<c<d
* Potential energy  stability of free Radical
EXAMPLE 6
Compare the bond energies of C – H bond
(at a, b, c, d, e and f position)
(2° benzylic) (2° benzylic, allylic) (2° benzylic, allylic) (1° benzylic)
CH3 – CH2 – –CH2 – CH = CH – CH2 – –CH3

(a) (b) (c) (d) (e) (f)
vinylic vinylic
b>e>a>f>c=d?
Stability order of free Radical that might be formed after removal of H (Homolytically) from the given carbon.
 e<b<a<f<c =d
(C – H bond energies)
• In the above compound while comparing 2° benzylic allylic stability at two given position
CH2 CH2
and
CH3 CH2 – CH3
while drawing the resonating structure of the
CH2 CH2 CH2
CH3 CH3 H–C–H
(Here inspite of Resonace three  (C – H) bond are available for no bond Resonance.
CH2
 Therefore extra stable than which have only two  (C – H) bond for Hyper conjugation.
CH2CH3
Therefore 2° benzylic allylic corresponding to structure (a) is more stable than that of structure (b)
GOC
EXAMPLE 7
Compare the stability of the following free Radical
CH2 CH3
CH 2 = CH – CH 2
(d)
(b) (c)
(a)
SOLUTION
CH2
CH3
CH 2 = CH – CH 2
(a) (b) (d)

(c)
1° allylic 2° allylic + 2H
3° allylic + 5H
CH2 – CH = CH2
(d)
(only resonance)
CH2
H
H  c>b>a>d
(Resonance + 2H)
EXAMPLE 8
Compare the potential energy of CH3 – CH3, CH2 = CH2 CH  CH
SOLUTION
After making free Radical of the above compounds
 
CH3 – C H2  CH  C
, CH2  C H
(most  stable ) (least stable )
  
CH3 – C H 2  CH2  C H  CH  C
(a) (b) (c )
a>b>c
GOC
CARBOCATION
 
C H3  Methyl Carbocation CH3 – C H2  Ethyl Carbocation

CH3 – C H – C H2  Isopropyl Carbocation
|
CH3
Properties of Carbocation :
1. it is positivly charged species 2. it has sixtet of electrons i.e. diamagnetic
3. it is formed by heterolysis 4. it is generally formed due to polar solvent
Structure :
(sp2) Triangular planer
Stability :
Its stability can be determined with the help of Inductive effect, Hyper conjugation and Resonance effect.
Stability of Carbocation :
 +
C H3 , CH3 CH2
(+ I effect)
1
ch arg e 
Stability
 +
C H3 , < CH3 CH2 (stability order)
Stability of carbocation can also be determined by Hyper conjugation (no bond Resonance)
H H+
| + |
H – C – CH2 H – C = CH2
| |
H H
+ +
CH3 – C – CH3 CH3 – CH + +
| > | > CH3 – CH > CH3
CH3 CH3
9  C – H bond 6 C – H bond 3 C – H bond
ALLYLIC CARBOCATION
+ +
CH2 = CH – CH2 CH2 – CH = CH2
allylic carbocation Actual Resonance
BENZYLIC CARBOCATION
+
CH2 CH2 CH2 CH2
 
ph 2 C H  7 Re sonating strucutre ph 3 C  10 Re sonating strucutre
   
ph 3 C  ph2 C H  (CH3 )3 C  ph C H2
GOC
EXAMPLE 9
Compare the stability of th following carbocation
  
(a) CH3 – C H2 (b) CH 2  C H (c) CH  C
sp2 sp
 more s charactor
 more electronegativity
 +ve charge on more electronegative element is symbol of unstability.
a>b>c
EXAMPLE 10
Compare the stability of the following compounds
   
(a) C H2 – CF3 (b) C H2 – CCl3 (c) C H2 – CBr3 (d) C H3
SOLUTION
d>c>b>a
F being most electron attracting group decreases the e– density from positively charged C-atom and decreases
the charge density and makes the carbocation less stable.
EXAMPLE 11
Compare the stability of the following carbocation :
+ +  
(a) CH2 – F (b) CH2 – Cl (c) C H2–Br (d) C H2 – I
SOLUTION
Due to greater size of Iodine, its L.P. will not be available for coordinate bond. Therefore L.P. would not stabilize
corbocation.
+ making it most stable
In case of F due to its small size its lone pair can be easily coordinated to C
a>b>c>d (Stability)
* By coordination the carbocation completes its octet and structure having complete octet of its atom is supposed to
be most stable.
+ .. + +
..
CH2 – F.. CH2 F CH2 = F

(Each atom has its full octet)
+ +
C A ph3C
*
(stability)
Note :
In Resonating Structure of ph3 C , at least one C gets sixtet of e– and hence less stable than coordinated compound.
EXAMPLE 12
Compare the stabilities of the following corbocation
  
(a) CH2NH2 (b) C H2 – OH (c) C H2 – F
SOLUTION
N, O, F belongs to same period
 In period Electronegativity of the atom is deciding factor
 F being most electronegative, holds its e– pair very firmly.
 Its L.P. will not be easily available for coordination.
 Stability by it will be minimum.
a>b>c
GOC
EXAMPLE 13
Compare the following corbocation in order of their stability.
 
(a) C H2 – Cl (b) C H2 – OH
SOLUTION
If periods of atoms which have to donate their electrons for coordination (for stability) is different then atomic size
will be deciding factor. The atom whose size is greater will be unable to make its e– pair available for coordination.
b>a
EXAMPLE 14
Compare the stability of the following compounds
+  +
(a) CH3 CH2 – CH2 (b) CH2  CH – C H2 (allylic ) (c) ph CH2 – CH2
SOLUTION
 more s-character
 more e.n.
 attracts e–
 reduces, stability
b>a>c
CARBANION
1. it is a –ve charged species
2. it has octet of electrons.
3. diamagnetic
Strucutre :
* if –ve charge is in Resonance then the hybridisation of carbanion is sp2 (Triangular planer shape)
* If –ve charge is not in Resonance then the hybridisation of carbanion is sp3 (pyramidal)
Stability :
Its stability can be determined with the help of
(1) Inductive effect
(2) Resonance effect
EXAMPLE 15
– –
CH3 , CH3 CH2
(a) (b)
a > b (stability)
* Stability of the carbanion is as follows
– – – – –
Ph3C > Ph2CH > Ph CH2 > CH2 = CH – CH2 > CH  C >
– – – – –
CH2 = CH > CH3 > CH3 – CH2 > (CH3)2CH > (CH3)3C
EXAMPLE 16
Compare the stability of the following carbacation
+
 
CH  C CH2  C H
(a) (b) (c)
actual (sp ) sp 2
SP2
SOLUTION
c>a>b
GOC
EXAMPLE 17
Compare the stability of the following carbanion
– –
CH  C
–
sp CH2 = CH
(a) (b) –ve charge is attracted by (c)  become more stable
sp hybridised carbon sp2
tending sp (most electronegative)
SOLUTION
b>a>c
EXAMPLE 18
Compare the stability of the following carbanion
– – –
(a) CH – CF (b) CH – CCl (c) CH – CBr
2 3 2 3 2 3
SOLUTION
a>b>c
EXAMPLE 19
Arrange the following anion order of their stability
(a) Cl–, (b) Br–
–
(c) F (d) I– (maximum size)
 maximum dispersion of –ve charge
 max stability
SOLUTION
d>b>a>c
EXAMPLE 20
Compare the stability of the following
(a) CH 3 (b) NH2 (c) OH (d) F
SOLUTION
Same period element (C, N, O, F)
 Stability  E.N. of the atom
d>c>b>a
EXAMPLE 21
Compare the acidic strength
(a) HCl (b) HF
(C) HBr (D) HI
SOLUTION
Acidic strength  stability of the anion formed (conjugate base)
as we know I– > Br– > Cl– > F–
 H I > HBr > HCl > HF
EXAMPLE 22
Compare the Acidic strength of the following
(a) NH3 (b) PH3
(c) AsH3 (d) SbH3 (e) BiH3
SOLUTION
Anion formed from there acids are
N H2  P H2  AsH 2  S bH2  B iH 2
(Stability )
 acidic strength e > d > c > b > a
GOC
EXAMPLE 23
Compare the acidic strength of the following comounds CH4, NH3, H2O, HF
SOLUTION
The conjugate base of the given acid is as follows
– – – –
CH3 , N H2 , O H, F
we have already proved that
– – – –
F > O H > NH2 > CH3 (Stability)
 HF > H2O > NH3 > CH4 (acidic strength)
EXAMPLE 24
Compare the stability of the following carbanion.
– – – –
CH2 CH2 CH2 CH2
NO2
(–M, –I)
(a) (b) (c) (d)
NO2
(–I) NO2
(–M, –I)
SOLUTION
d>c>b>a
* +M or –M is not distance dependent
EXAMPLE 25
compare the stability of the following carbocation
+
+ CH2
CH2
+ +
CH2 CH2
NO2
(a) (b) (c) (d) (–M, –I)
NO2
NO2
(–I) (–M, –I)
SOLUTION
a>b>c>d
EXAMPLE 26
Compare the stability of the following carbocation.
+
CH2 + + +
CH2 CH2 CH2
(a) (b) (c) (d)

Cl
(+M, –I) NH2 OH OCH3
(+M) (+M) (+M)
but –I > +M for Cl
SOLUTION
+M (OH) > +M (OCH3)
b>c>d>a
GOC
EXAMPLE 27
Compare the stability of the following carbocation
+ +
CH2 CH2 +
CH2
(a) (b) (c)
F (–I > +M) Cl
SOLUTION
c>a>b
EXAMPLE 28
Compare order of dehydration of the following alcohols :
OH
| OH
(a) C – C
|
–C
(b) | (c) C – C – C – OH
C–C–C
C
SOLUTION
After formation of carbocation
+ + +
C–C–C , C–C–C
, C–C–C
|
C
Since 3° carbocation is most stable therefore it will show greatest tendency to lose water as after lose of water
it comes in stable form.
TYPES OF REAGENT
1. Electrophilic reagent : All electron deficient atom or group of atoms is known as Electrophilic reagent, the
electrophile attacks at the electron rich centre.
(a) all positively charged species are electrophile
H+, NO2+, Br+, Cl+, etc.
(b) The compound in which the octet of central atom is not complete
BF3, AlCl3, ZnCl2, etc.
(c) all the compound in which the central atom can expand its octet
SnCl4, SiCl4, etc.
(d) all polarising functional group are electrophile as well as nuelophile
C = O , –C  N, etc.
Nucleophile :
All electron rich compounds are nucleophile and attack at the electron deficient centre.
(a) all negatively charqed species
H–, Cl–, NO2–, Br–, CH3– etc.
(b) the compound in which the central atom has lone pair of electron.
 
NH3, H2O, R N H2 , R O H etc.
(c) all organometallic compounds are nucleophile
R – Mgx, RLi, R2Cd
(d) The compound having  e– density, CH2 = CH2, etc.
GOC
Nucleophilicity :
The power of nucleophile is known as nucleophilicity .
 The nucleophilicity of negative charge is greater than the nucleophilicity of lone pair
O H  H2 O
CH3 O  CH3 OH
 If lone pair or –ve charge is present on the different atom then less electronegativity, more will be the nucleophilicity.
CH3 – , NH2 – , OH – , F –
Nucleophilicity CH3 –  NH2 –  OH–  F –

 NH3 < PH3 < AsH3 < SbH3 < BiH3 (Nucleophilicity)
 If –ve charge or lone pair of electron is present on the same atom then the less stable –ve charge will be the better
nucleophile
OH– , CH3 O, CH3 COO –
CH3O –  OH–  CH3COO– (nucleophilicity)
ACTIVATOR & DEACTIVATOR

The groups in benzene which show +M effect or +I effect Increases the electron density on benzene it means
they activate the ring towards electrophile and known as activator.
NH2 OH
, , –CH3,–OR,–NHMe,
COO– O–
The groups which shows –M or –I effect (resultant) decreases the e– density from benzene ring. It means they
deactivate the ring towards electrophile
CHO NO2 COOH SO3H NO CCl3 CN NC
, , , , , , , etc.
ORTHO, PARA & META DIRECTOR

The groups which shows +I (resultant) or +M effect then negative charge is developed at the ortho & para
position. Therefore electrophile attack at the ortho & para position and the groups are known as OP director.
G G+ G+ G+
– –
–
+M Effect
• The groups which shows –M effect or – I effect (resultant) then +ve charge is developed at the ortho & para
position this means electron density is minimum at the ortho & para positions and electronphile will attack at the
meta position the groups are known as meta director.
CCl3 CN NO2 NO NC
, , , , ,
GOC
O O
O
COOH CHO SO3H N=O O N – O– N – O– N – O–
+ +
, ,
HEAT OF HYDROGENATION(H.O.H)
It is the amount of energy realeased when one mole of H2 is added to any unsaturated system.
CH2 = CH2 + H2  CH3 – CH3 + energy
HOH is exothermic process H = – ve
*HOH No. of -bonds in compound
If no. of -bonds is same then
1
*HOH  stabilityof compound
 In case of alkene
1 1
** HOH  stability of compound  No. of α H
Example
a + H2 + 29 kcal
b + 2 H2 + 58 kcal 55 kcal
(expected) (actual)
c + 3 H2 + 87 k cal 51 k cal
(expected) (actual)
b>c>a
Energy
HOH
+H2 +2H2 +3H2
H= – 29 58 87
H= – 55 H=– 51
RE = 3 k Cal RE = 36 k Cal
GOC
Aromaticity (Huckle Rule) :
Cyclic, planar and completely conjugated system with (4n+2) electrons (where n = 0, 1, 2, 3, ......) are known as
Aromatic compounds. These compounds gain extra stability which is known as aromaticity.
Example
O
Anti aromatic compounds : Cyclic planar and completely conjugated system, with 4n electrons (where n = 1,
2, 3,....) are known as Antiaromatic compounds. These compounds are highly unstable & paramagnetic in nature
due to presence of unpaired electrons.
Ex.
(i) Cyclic  (i) Cyclic 

(ii) Planar  (ii) Planar 
(iii) Comp. conjugated  (iii) Comp. conjugated 
(iv) 4n = 4, n = 1 (iv) 4n = 4, n = 1
Both the Compounds are anti aromatic.

Note : Anti aromatic compounds have tendency to get dimerise and leading to the formation of non aromatic compounds.
Some examples of Arromatic(A), Non-arromatic(NA) and Anti-arromatic(AA)
(1) (A) (2) (AA) (3) (AA)
(4) (NA) (5) (AA) (6) (A)
O O–H OH
+
H
(7) (A)
Br
(8) AgNO3/ (A)
(9) (A) (2e) (10) (A) (6e)
(11) (NA) (12) (NA)
GOC
(13) (AA) (4e) (14) (A) (15) (NA)
O Br H H
+
H AgNO3 NH2
(16) (A) (17) (A) (18) (AA)
Br O
+
AgNO3 H
(19) (A) (20) (AA) (21) (AA)
O
(22) (A) (23) (A) (24) (A)

N N
H
O
(25) (A) (26) (A) (27) (NA)

O N=N
S
Acidity & Basicity
HA H + A
Acid Conjugate base
Note :
More stable the conjugate base (i.e., A ), more will be the forward reaction which results more acidic nature of
HA.
EXAMPLE 29
Compare the acidic strength of the following acids.
(a) C – C – C – COOH
(b) C = C – C – COOH
(c) C  C – C – COOH
SOLUTION
The acid whose conjugate base is most stable will be more acidic.
After forming conjugate base from the above acids.
(a) C – C – C – COO–
sp3
(b) C = C – C – COO–
sp2
(c) C  C – C – COO–
sp
It is clear that sp hybridised carbon being most electronegative will decrease e– density from O most effectively
making the conjugate base most stable.
c>b>a (acidic strength)
GOC
EXAMPLE 30
Which is more acidic between the two
(a) CHF3 (b) CHCl3
SOLUTION
CHF3 > CHCl3
If we consider the –I effect of F and Cl But this effect will not be considered here
After the removal of proton
F Cl
(a) – C F (b) –
C Cl
F Cl
(vacant d-orbital available where C will coordinate its electron) (p – d bonding)
 a < b (acidic strength)
EXAMPLE 31
Compare the acidic strength of the following
(a) CHF3
(b) CHCl3
(c) CHBr3 (p – d bonding in Br is not as much as effective as in Cl due to large size of Br)
SOLUTION
CHCl3 > CHBr3 > CHF3
EXAMPLE 32
(a) CH (CN)3 (b) CH (NO2)3 (c) CHCl3
SOLUTION
After removing H+
C N
–
C
CN (Resonance) In its resonating structure, –ve charge will be on N)
CN
O
N=O
–
C
N=O (Resonance) (– In its resonating structure –ve charge will reside on O
O N=O
O
 more effective Resonance
Cl
–
C
Cl (p – d)
Cl
b>a>c
* –ve charge on O is more
stable than –ve charge on N as O is more electronegative than N.
* P – d Resonance < Actual Resonance
EXAMPLE 33
(a) CH  CH (b) CH2 = CH2 (c) CH3 – CH3
SOLUTION
–
CH  C > CH2  CH > CH3 – CH2
sp sp2 sp3
(Stability of the conjugate base)
 a>b>c (acidic strength)
GOC
EXAMPLE 34
Compare the acidic strength of the following :
(a) CH3 – CH2 – CH2 – COOH
(b) CH3 – CH – CH – COOH
|
Cl
(c) CH3 – CH – CH – COOH
|
F
(d) CH3 – CH – CH – COOH
|
NO 2
SOLUTION
d>c>b>a
EXAMPLE 35
Compare the acidic strength of the following :
(a) H2O (b) H2S (c) H2Se (d) H2Te
SOLUTION
Conjugate base is in an stability order
OH  HS  HS e  H2 Te
 H2O < H2S < H2Se < H2Te (acidic strength)
EXAMPLE 36
Compare the acidic strength of the following compound
CH3 CH2Cl CH2F
(a) (b) (c) (d)
SOLUTION
After forming conjugate base of the above
CHCl
CH2
–
p – d bonding due
–ve charge is not vacant d-orbital of Cl
in resonance
(most stable)
CHF
C – I effect of F
decrease e– density
from C making the
carbanion stable
c>d>b>a
GOC
EXAMPLE 37
Compare the reactivity of the following compounds with 1 mole of AgNO3
CH2Cl
Cl CH2Cl CHCl2
(a) (b) (c) (d)
CH3
SOLUTION
After removing Cl–
+
+ CH2
(+ve charge is not on resonance

 least stable)
+
CH – Cl
(most stable as L.P. of Cl will be coordinated to +ve charge completing the octet of each atom and making the
corbocation most stable)
+
CH2
(By hyper conjugation)
CH3
extent of +ve charge decreases stability increases
EXAMPLE 38
Compare the acidic strength
CH3
CH3 CH3 CH3
NO2
(a) (b) (c) (d)
NO2
NO2
SOLUTION
After making conjugate base
–
CH2
CH2
CH2 CH2
NO2
(–I, –M)
NO2 NO2
(–I)
(–I, –M)
c>b>a>d
GOC
BASIC STRENGTH
+
A H
A+ – H
Basic strength directly depends on the availibility of lone pair for H+
EXAMPLE 39
Compare the basic strength of following
SOLUTION
(a) NH3
(b) PH3
(c) AsH3 Basic strength
(d) SbH3
(e) BiH3
EXAMPLE 40
Compare the basic strength of the following
(a) C H3 (b) NH2
(c) O H (d) F
SOLUTION
C H3 , NH2 , O H , F
CH4 < NH3 < H2O < HF
(acidic strength)
– – – –
CH3 > NH2 > OH > F
(Basic strength)
* Strong Acids have weak conjugate base.
– – – –
CH3 > NH2 > OH > F
(Nucleophilicity)
* For the same period
less electronegativity, more nucleophilicity as more electronegative element has less tendencey to give its electron
pair.
EXAMPLE 41
Which is more basic O H or HS ?
SOLUTION
OH > HS
–
Which is more basic NH3 or NH
2
forming conjugate acid
+
NH 4 > NH 3 (acidity)
–
 NH3 < NH2 (Basicity)
COMPARISON OF BASICITY OF AMMONIA AND ALKYL AMINES :

EXAMPLE 42
Compare the basic strength of the following NH3, CH3NH2, (CH3)2NH, (CH3)3N Factors which affect the
basicity of Amines
(1) steric effects (2) Inductive effect (3) solvation effect.
GOC
• The base whose conjugate acid is more stable will be more acidic forming conjugate acid of the given base
   
NH4 , CH3 NH3 , (CH3 )2 NH2 , (CH3 )3 NH
Stability order of conjugate acid
   
(CH3 )3 NH  (CH3 )2 NH2  CH3 NH3  NH4
(due to +I effect)
Therefore basic strength
(CH3)3N > (CH3)2NH > CH3NH2 > NH3
(vapor phase or gaseous is phase or in Non polar solvent)
In Aqueous solution or in polar solvent
(CH3)2NH > CH3NH2 > (CH3)3N > NH3
• In aqueous solution, the conjugate acids form H-bonds (intermolecular) with water molecules and stabilise them
selves conjugat acid of 1° amine which has largest no. of H-atoms form maximum H-bond with water and is most
stable. Consequently 1° amine is most basic.
• Due to steric effect 1° amine is considered more basic as compared to 3° amine as lone pair is hindered by three
alkyl group and less available for H+.
Considering the combined effect of the three (Inductive, solvation and steric effect) we can conclude that
2° > 1° > 3° > NH3
• Aromatic amines are least basic as their lone pair is in conjugation and less avaibable for protonation.
EXAMPLE 43
N NH2
(no Resonance as
ring will break if we
draw the resonating
(a) structure) (b) (c)
(Resonance)
(most basic)
(if L.P. will be participate in Resonance, then molecule becomes aromatic)

 Hence L.P. will have a greater tendency to take part in Resonance and will be less available for H+
 This compound will be least basic.
EXAMPLE 44
sp
Common for all
(a) CH  C – CH2 – NH2
(b) CH2 = CH – CH2 – NH2
sp2
(c) CH2 – CH2 – CH2 – NH2
sp3
SOLUTION
sp hybridised carbon being most electronegative will attract e– density from nitrogen and will make it less available
for H+. Hence basicity decreases.
c>b>a
GOC
EXAMPLE 45
Compare the basic strength
H
|
N H
|
N
(a) O (b)
(–I of O at attracts e– density
from N making it less basic)
a<b
EXAMPLE 46
Compare the basicity of the following compounds

(a) CH3 – CH2 – CH = CH – N H2
(b) CH 3 – CH2 – CH 2 – CH 2 – NH 2
sp3
(c) CH2 = CH – CH2 – CH2 – NH2
sp2
(d) CH  C – CH2 – CH2 – NH2
sp
SOLUTION
In part (a) the lone pair of nitrogen in Resonance therefore will be less available for H+ making it least basic
among all followed by sp, sp2, sp3 hybridised carbon atoms.
b>c>d>a
EXAMPLE 47
Compare the basicity of the numbered nitrogen atoms.
(As L.P. in
Resonance)
H sp2 sp2
|
N N
H–N 1 2 3
sp3 N
as L.P. is not in Resonance

(or in conjugation)
SOLUTION
The planerity of ring will be destroyed if L.P. will take part in Resonance.
Basicity order of Nitrogen follows the order
N(sp3) > N(sp2) > N(sp)
1 > 3> 2
sp2 sp2
(In this sp2, l.p. is in Resonance with ring hence will be less available for H+ therefore it will be least basic)
GOC
EXAMPLE 48
NH2
NH2
NH2
(a) (b) (c)
NO2 NO2
SOLUTION
In part (a) NO2 is at p-position Hence will attract e– density by both –M and –I
In part (b) NO2 is at m-position hence will attract e– density by –I only
There is no such effect in part (c)
 Availibity of L.P. on nitrogen in part (a) is minimum followed by b and then c.
c>b>a
Ortho effect :
The ortho substituted aniline are less basic than aniline and ortho substituted benzoic acids are more acidic than
benzoic acid.
• Ortho effect is valid only for benzoic acid and aniline.
NH2 NH2
NO2
e.g. < Also
NH2 NH2
CH3
<
EXAMPLE 49
Compare the basic strength of the following :
NH2
NH2
NH2
NH2
CH3
(a) (b) (c) (d)

CH3 CH3
(+I) (+I)
(+I, Hyperconjugation)
SOLUTION
a>b>d>c
* Due to ortho effect d > c
if c is less basic than d then it will be certainly less basic than b as b is more basic than d.
EXAMPLE 50
Compare the basic strength of the following :
NH2
NH2
NH2 NH2
NO2
(a) (b) (c) (d)
NO2 NO2
GOC
SOLUTION Do your selves

S.I.P  Steric inhibition of Protonation (ortho effect)
+
NH2 NH3
G G
H+
after protonation, repulsion increases therefore ortho substituted aniline is less basic than aniline
S.I.R  Steric inhibition of resonance
NH2
CH3
NH3
CH3 NO2
(a) CH3 (b)
NO2
(Shows –I as well as
– M this means delocalisation
(Shows only –I effect) of e– is more)
GOC
Exercise - 1 Objective Problems | JEE Main

Basic Concept (Bonding)
1. Bond formation is:
(A) always exothermic (B) always endothermic
(C) neither exothermic nor endothermic (D) sometimes exothermic and sometimes endothermic
2. CH2 = CH – CN
3 2 1
C1 - C2 bond of this molecules is formed by:
(A) sp3-sp2 overlap (B) sp2-sp3 overlap (C) sp-sp2 overlap (D) sp2-sp2 overlap
3. Find out the hybridisation state of carbon atoms in given compounds from left to right.
CH3 – CH = CH – CH = C = CH – C  C – CH3
(A) sp3 sp2 sp2 sp2 sp sp2 sp sp sp3 (B) sp3 sp2 sp2 sp sp sp sp sp sp3
(C) sp3 sp2 sp2 sp2 sp2 sp2 sp sp sp3 (D) sp3 sp sp sp2 sp sp2 sp sp sp3
4. Total number of and -bonds are in naphthalene is:

(A) 5 and 18 (B) 6 and 19  (C) 5 and 19 (D) 7 and 26
5. In which of the following molecules resonance takes place through out the entire system?
(A) (B) (C)
NH
COOCH3
(D) | (E)
COOCH3
Inductive Effect
6. The inductive effect -
(A) implies the atom’s ability to cause bond polarization
(B) increases with increase of distance
(C) implies the transfer of lone pair of electrons from more electronegative atom to the lesser electronegative
atom in a molecule
(D) implies the transfer of lone pair of electrons from lesser electronegative atom to the more electronegative
atom in a molecule
CH3
7. When – CH3, CH3 – CH – and CH3 – C – groups are introduced on benzene ring then correct order of their
CH3 CH3
inductive effect is
CH3 CH3
(A) CH3 – > CH3 – CH – > CH3 – C – (B) CH3 – C – > CH3 – CH – > CH3 –
CH3 CH3 CH3 CH3
CH3 CH3
(C) CH3 – CH – > CH3 > CH3 – C – (D) CH3 – C – > CH3 – > CH3 – CH –
CH3 CH3 CH3 CH3
GOC
8. Express in decreasing order of (+) -

CH3
CH3 CH3–CH–CH2–
(a) CH3CH2 – CH2 – (b) CH3 – (c) CH3–C–CH2–CH3 (d) CH3–C– (e)
CH2CH3
CH3
Correct answer is -
(A) (c) > (d) > (e) > (a) > (b) (B) (d) > (a) > (b) > (c) > (e)
(C) (a) > (b) > (c) > (d) > (e) (D) (a) > (b) > (c) > (e) > (d)
9. Consider the following carbanions

(i) CH3 – CH2 (ii) CH2 = CH (iii)
Correct order of stability of these carboanions in decreasing order is :
(A) i > ii > iii (B) ii > i > iii (C) iii > ii > i (D) iii > i > ii
Inductive & Acid, Base
10. In which of the following compounds is hydroxylic proton the most acidic ?
F O O
H H
(A) O (B) I O
H (C) (D)
H F F
11. Consider following acid

ClCH2COOH, CH3COOH, CH3CH2COOH
I II III
Correct order of their pH value is :
(A) III < II < I (B) I < II < III (C) I < III < II (D) II < I < III
12. Which among the given acid has lowest pKa value -
(A) Chloroacetic acid (B) Bromoacetic acid (C) Nitroacetic acid (D) Cyanoacetic acid
13. Arrange in decreasing pKa

(a) F – CH2CH2 COOH (b) Cl – CH – CH2 – COOH
Cl
(c) F – CH2 – COOH (d) Br – CH2 – CH2 – COOH
Correct answer is :
(A) b > d > a > c (B) a > c > d > b (C) d > a > b > c (D) d > b > a > c
14. The correct order of increasing acid strength of the compound is :

Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO2 H
Me
(A) d < a < c< d (B) d < a < b < c (C) a < d < c < b (D) b < d < a < c
15. The correct order of increasing basic nature of the bases NH3, CH3NH2 and (CH3)2NH is gas phase
(A) NH3 < CH3NH2 < (CH3)2NH (B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH (D) (CH3)2NH < NH3 < CH3NH2
16. Arrange basicity of the given compounds in decreasing order -

(a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 (c) CH  C – NH2
(A) a > b > c (B) a > c > b (C) c > b > a (D) b > c > a
17. Which one of the following is the strongest base in aqueous solution ?
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
RESONANCE
GOC
18. In which of the following molecules, all atoms are not coplanar ?
O
O
(A) (B) (C) (D)

O
O O
19. (I) CH2 = CH – CH = CH2 (II) CH2 – CH = CH – CH2 (II) CH2 – CH = CH – CH2
Among these, which are canonical structures ?
(A) I and II (B) I and III (C) II and III (D) all
O O O
|| | |
20. C C C
H OH H OH H OH
I II III
Among these canonical structures, the correct order of stability is

(A) I > II > III (B) III > II > I (C) I > III > II (D) II > I > III
21.
Among these canonical structures which one is least stable ?

(A) I (B) II (C) III (D) IV
22. For phenol which of the following resonating structure is the most stable ?
OH OH
OH
(A) (B) (C) (D) All have equal stability
23. The most stable resonating structure of following compound is :
O=N
.. ..N = O
..
(A) O = N N=O (B) O – N N–O
(C) O = N N=O
(D) O – N N=O
GOC
24.
N N N N N
I II III IV V
Among these canonical structures of pyridine, the correct order of stability is :
(A) (I = V) > (II = IV) > III (B) (II = IV) > (I = V) > III
(C) (I = V) > III > (II = IV) (D) III > (II = IV) > (I = V)
25.
N N N N N
| | | | |
H H H H H
(I) (II) (III) (IV) (V)
(A) (III = IV) > (II = V) > I (B) I > (II = V) > (III = IV)
(C) I > (III = IV) > (II = V) (D) (II = V) > (III = V) > I
26. ‘M’ effect is the resonance of -

(A)  electrons only (B)  electrons only (C)  and  both (D) (+)ve and (–) charge.
27. Which of the following contain + M but -  effect -

(A) O = CH – (B) – NO2 (C) – Cl (D) CH3 –
m o
p OH
28.
m o
In phenol, -electron density is maximum on
(A) ortho and meta positions (B) ortho and para positions
(C) meta and pera positions (D) none of these
29. Which of the following compounds has maximum electron density in ring ?
NO2 OH O COO
(A) (B) (C) (D)
30. In which of the following molecules -electron density in ring is minimum?

NO2
NO2 OCH3 NO2
(A) (B) (C) (D)
H2N NO2
GOC
Exercise - 2 (Level-I) Objective Problems | JEE Main

Stability of Intermediate
1. Rank the following free radicals in order of decreasing stability
(I) C6H5 CH C6H5 (II) C6H5 – CH – CH = CH2
(III) CH3 – CH – CH3 (IV) C6H5 – CH – CH3
(V) CH3CH CHCH2 CH 2 (VI) CH3 – CH2 – C – CH3
CH3
(A) I > II > IV > VI > III > V (B) VI > V > IV > III > II > I
(C) I > II > III > IV > V > VI (D) I > IV > VI > V > II > III
2. Rank thefollowing radicals in order of decreasing stability
(I) (II) (III) (IV)
(A) III > II > I > IV (B) III > IV > I > II (C) II > III > I > IV (D) IV > II > I > III
3. Select the most stable carboncation among the following -


(A) (B)

(C) (D) 
4. Write correct order of stability of following carbocations:
CMe3 CMe3 CMe3

(I) (II) (III) CMe2 (IV)
Me Me Me
Me
Me Me Me
(A) I > II > III > IV (B) III > II > I > IV (C) III > I > II > IV (D) III > II > IV > I
5. Arrange the following carbocations in the increasing order of their stability.
(I) (II) (III)
(A) I > II > III (B) I > II = III (C) I > III > II (D) III > I > II
6. Which of the following carbocation will be most stable ?

O CH3
(A) H C + (B) H C +
3 CH CH3 3 CH
CH3
+
(C) H C + (D) H3C C
3 CH CH3
CH3
GOC
7. Statement-1: Me – CH2 is more stable than MeO – CH2

Statement-2: Me is a +I group whereas MeO is a –I group.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for statement-1.
(C) Statement1 is false, statement-2 is true.
(D) Statement1 is true, statement-2 is false.
8. Ease of ionization to produce carbocation and bromide ion under the treatment of Ag will be maximum in which
of the following compounds?
O N Br
(A) (B) (C) N Br (D)
O Br Br CH3
Ph
9. In which of the following pairs, first species is more stable than second ?
O O O O O
–
(A) CH3CH2O– or CH3CO (B) CH 3CCHCH2CH or CH3CCHCH3
O O
O O
(C) CH 3CHCH2CCH 3 or CH 3CH2CHCCH 3 (D) N– or N–
10. The order of stability of the following carbanion is:
(I) CH3CH2 (II) (III) (IV)
(A) I > II > III > IV (B) I > III > II > IV (C) IV > III > II > I (D) III > IV > I > II
11. Arrange the carbonions,

(CH3 )3C, CCl3, (CH 3) 2CH, C6H5CH 2 in order of their decreasing stability
(A) (CH3)2CH > CCl3 > C 6H 5CH 2 > (CH 3) 3C (B) CCl3 > C 6H 5CH2 > (CH3)2CH > (CH 3) 3C
(C) (CH3)3C > (CH3)2CH > C6H5CH 2 > CCl 3 (D) C6H5CH2 > CCl3 > (CH3)3C > (CH3)2CH
1 1 1
2 2 2
12. 3 3 3
4 4 4
There are three canonical structures of napthalene. Examine them and find correct statement among the following:
(A) All C–C bonds are of some length (B) C1-C2 bond is shorter than C2-C3 bond.
(C) C1-C2 bond is longer than C2-C3 bond (D) None.
13. Which of the following has longest C – O bond:
O
O O O
(A) (B) (C) (D)
CH2
GOC
14. Among the following molecules, the correct order of C - C bond length is :
(A) C2H6 > C2H4 > C6H6 > C2H2 (B) C2H6 > C6H6 > C2H4 > C2H2 (C6H6 is benzene)
(C) C2H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6
AROMATICITY
15. In which of the following molecules -electron density in ring is maximum?
NO2 O NH2 OCH3
(A) (B) (C) (D)
16. (I) (II) (III)
Which of these cyclopropene systems is aromatic?

(A) I (B) II (C) III (D) all of these
17. (I) (II) (III)
Which of these species is anti-aromatic ?

(A) I only (B) II only (C) III only (D) both II and III
18. Which of the following compouds is not aromatic?
O O
(A) (B) (C) (D)
O O O
O
O
19. N=N
The most stable canonical structure of this molecule is :
(A) N=N (B) N=N (C) N N (D) All are equally stable
20.
O
The most stable canonical structure of this molecule is:
O O O O
(A) (B) (C) (D)
GOC
21. (I) (II) (III)
The barrier for rotation about the indicated bonds Will be maximum in which of these three compounds ?
(A) I (B) II (C) III (D) same in all
22. Identify the odd species out Which of the species among the following is different from others ?
(A) (B) (C) (D)
23. Which of the following heterocyclic compounds would have aromatic character ?
N N N–H
(A) (B) N–H (C) (D) N–H
N N–H
24. Which one of the following carbonyl compound when treated with dilute acid forms the more stable carbocation
?
CH3
O HO O
|| ||
(A) CH3 – C – CH3 (B) (C) (D) C6H5 – C – C6H5
HO OH
O O
25. The order of the rate of formation of carbocations from the following iodo compound is:
(I) (II) (III)

H I H I H I
(A) I > II > III (B) I > III > II (C) III > II > I (D) II > III > I
26. Write correct order of reactivity of following halogen derivatives towards AgNO3.
Cl
(I) (II) CH2 = CH – Cl (III) Et3 C – Cl (IV) PhCH2Cl
(V) Ph3C – Cl
(A) I > V > IV > III > II (B) V > IV > I > III > II
(C) V > I > IV > III > II (D) I > V > III > IV > II
27. Which of the following species is not aromatic ?
(A) (B) (C) (D)

O O
GOC
28. (I) (II) (III)

O N
N
|
H
The aromatic character is maximum in which of these three compounds ?
(A) I (B) II (C) III (D) Same in all
29. CH3COOH CH3COONa CH3CONH2

(I) (II) (III)
Among these compounds, the correct order of resonance energy is :
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III
O O O O
30. (I) (II) (III) (IV)
Among these compounds, which one has maximum resonance energy ?

(A) I (B) II (C) III (D) IV
31. (I) (II)
Which of the following orders is correct for the resonance energy of these two compounds ?
(A) I > II (B) II > I
(C) I = II (D) there is nothing like -electron energy
GOC
Exercise - 2 (Level-II) Multiple Correct | JEE Advanced

RESONANCE
1. Which of the following statements is (are) true about resonance.

(a) Resonance is an intramolecular process.
(b) Resonance involves delocalization of both  and  electrons.
(c) Resonance involves delocalization of  electrons and lone pair only.
(d) Resonance decreases potential energy of a molecule.
(e) Resonance has no effect on the potential energy of a molecule.
(f) Resonance is the only way to increase molecular stability.
(g) Resonance is not the only way to increase molecular stability.
(h) Any resonating molecule is always more stable than any nonresonating molecule.
(i) The canonical structure explains all features of a molecule.
(j) The resonance hybrid explains all features of a molecule.
(k) Resonating structures are real and resonance hybrid is imaginary.
(l) Resonance hybrid is real and resonating structures are imaginary.
(m) Resonance hybrid is always more stable than all canonical structures.
2. Resonance energy will be more if

(a) canonical structures are equivalent than if canonical structures are non-equivalent.
(b) molecule is aromatic than if molecule is not aromatic.
3. A canonical structure will be more stable if

(a) it has more number of  bonds than if it has less number of  bonds.
(b) the octate of all atoms are complete than if octate of all atoms are not complete.
(c) it involves cyclic delocalization of (4n + 2) – electrons than if it involves acyclic delocalization of (4n + 2)  –
electrons.
(d) it involves cyclic delocalization (4n)  – electrons than if it involves acyclic delocalizationof (4n)  – electrons.
(e) +ve charge is on more electronegative atom than if +ve charge is on less electronegative atoms.
(f) –ve charge is on more electronegative atom than if –ve charge is on less electronegative atom.
4. Consider structural formulas A, B and C:
(A) (B) (C)

(a) Are A, B and C constitutional isomers, or are they resonance forms?
(b) Which structures have a negatively charged carbon?
(c) Which structures have a positively charged carbon?
(d) Which structures have a positively charged nitrogen?
(e) Which structures have a negatively charged nitrogen?
(f) What is the net charge on each structure?
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
GOC
5. How many of the following compounds give CO2 on reaction with NaHCO3 ?
,HCl, , , , , HCOOH , C2H5–OH , CH3COOH ,
6. Identify more stable canonical structure in each of the following pairs :
O O
(a) C .. C 
(b)
H OH H OH
 
(c) (d) C H  CH  CH  O 
 CH 2  CH  CH  O
2
(e)
7. In the following sets of resonance forms, label the major and minor contributors and state which structures would
be of equal energy. Add any missing resonance forms.
(a) CH 3—CH–CN CH3—CH=CN
O¯ O¯
+
(b) CH —C=CH–CH—CH
3 3 CH3—C—CH=CH—CH3
+
O O O¯ O
(c) CH —C–CH–C—CH CH3—C=CH–C—CH3
3 3
(d) [CH3 – CH – CH = CH – NO2 CH3 – CH = CH – CH – NO2 ]
NH2 NH2
(e) +
CH3—CH2—C—NH2 CH3—CH2—C = NH2
+
Resonance Energy
8. Which of the following pairs has higher resonance energy ?
(a) CH3COOH and CH3COONa (b) CH2 = CH – O and CH2 = CH – OH
COO O
(c) and (d) and
(e) and CH2 = CH – CH = CH – CH = CH2
GOC
9. Which of the following pairs has less resonance energy ?
(a) CO32– and HCOO– (b) and CH2 = CH – CH2–
(c) and CH2 = CH – CH = CH2 (d) and CH2 = CH – CH2+
10. Which of the following pairs has higher resonance energy ?
(a) and (b) and
(c) and (d) CH2 = CH – OH and CH2 = CH – CH = CH – OH
(e) and
AROMATIC
11. H–O–CN H–N=C=O
(Cyanic acid) (Isocyanic acid)
Loss of proton from these two acids produces
(A) same anion (B) different anions (C) same cation (D) different cations
12. Ease of ionization to produce carbocation and bromide ion under the treatment of Ag will be maximum in
whichof the following compounds ?
Br Br
(A) Br (B) (C) (D)
OCH 3 Br
Cl
13. 2SbCl5 P will be
Cl
(A) 2– (B) 2+ 2SbCl6 (C) (D) mixture of (a) and (b)
KH
14. P will be
n-BuLi
P
(A) (B) (C) mixture of (A) & (B) (D) none of these
GOC
15. Which one of the following statements is True:
(1) (2)
(A) PhLi adds to both compound with equal ease

(B) PhLi does not add to either of the compound
(C) PhLi react readily with 1 but does not add to 2
(D) PhLi react readility with 2 but does not add to 1
16. Correct order of rate of hydrolysis or rate of reaction toward AgNO3 for following compounds is :
Br Br
Br Br
(I) (II) (III) (IV)
(A) III > II > IV > I (B) I > II > III > IV (C) III > I > II > IV (D) III > II > I > IV
17. HClO4 P will be
H
ClO4 H
(A) (B) (C) ClO4 (D) Mixture of (A) & (B)
OH OH O
18. Ag ClO4 P
Cl
P will be :
(A) ClO4 (B) Ag (C) Mixture of (A) & (B) (D) None of these
19. Aromatic compounds is/are:
N O
(A) (B) (C) (D)
N B
N
|
H
20. Which of the following reactions give aromatic compound ?

O O
KH HI
(A) (B) HBr (C) (D) HBr
GOC
Stability of Intermediate
21. Write stability order of following intermediates:
CH 3
  |
(i) (a) CH 3  CH 2 (b) CH 3  CH  CH 3 (c) CH 3  C 
|
CH 3

 
(ii) (a) (b) (c)

(iii) (a) (b)  (c)

C H3
  |
(iv) (a) CH3  CH2 (b) CH3  CH CH3 (c) C H3  C 
|
C H3
(v) (a) (b) (c)
(vi) (a) (b) (c)
CH 3
  |
(vii) (a) HC  C (b) CH3  CH CH3 (c) CH 3 C
|
CH 3
(viii) (a) (b) (c)
(ix) (a) (b) (c)
(x) (a) (b) (c) (d)
 
(xi) (a) HC  C (b) CH2  CH (c) CH3  CH2
 
(xii) (a) HC  C (b) CH2  CH (c) CH3  CH2
GOC
22. Write stability order of following intermediates:

 
CH 2 CH2 CH2
(i) (a) (b) (c)
N OMe
O O
CH2 CH 2 CH2
CH2
(ii) (a) (b) (c) (d)
Cl N CN
º
O O
CH2 CH2 CH2

OH
(iii) (a) (b) (c)
OH
OH
CH2 CH2
(iv) (a) (b)

F Cl

(v) (a) CH 2 CH (b) CH2  CH3
O
O O O
(vi) (a) (b) (c)
CH2 CH2 –CH2
(vii) (a) (b) (c)
(viii) (a) (b) (c)
(ix) (a) (b)
(x) (a) (b) (c) (d)
(xi) (a) (b) (c)
GOC
 
CH 2 CH2 CH2

H
(xii) (a) (b) H (c) C H
C H H
H
H C H
H
CH2 CH2 CH2 CH2
(xiii) (a) (b) (c) (d)

CH3 CH2Me CH Me2 CMe3
Bond Length
23. In which of the following pairs, indicated bond is of greater strength :
(a) CH 3  CH 2  Br and CH 3  CH 2  Cl
 
(b) CH 3  CH  CH  Br and CH 3  CH  CH 3
 |
Br
(c) and CH 3  CH 2  Cl

(d) CH 2  CH  CH  CH 2 and CH 2  CH 2  CH 2  CH 3
 
(e) and
24. In which of the following pairs, indicated bond having less bond dissociation energy :
(a) and CH 2  CH 2

(b) CH 3  C  CH and HC  CH
 
(c) and
(d) and
(e) and (f) and
GOC
25. Compare the C–N bond-length in the following species:
(i) (ii) (iii)
26. Which of the following statements would be true about this compound:
NO2
5
1 3
NO2 NO2
Br
(A) All three C – N bonds are of same length.
(B) C1 – N and C3 – N bonds are of same length but shorter than C5 – N bond
(C) C1 – N and C3 – N bonds are of same length but longer than C5 – N bond
(D) C1 – N and C3 – N bonds are of different length but bot are longer than C5 – N bond.
27. Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane
(c) or
28. Consider the given reaction:
Pd / C
+ 3H2 
In the above reaction which one of the given ring will undergo reduction?
Heat of Hydrogeneration & Combustion

29. Compare heat of hydrogenation (Decreasing order)
(a) heat of hydrogenation
(i)
(ii)
GOC
(b) and
(c) and
(d) and
(e) CH2 = CH – CH and
CH2 = C
30. (I) Stability order and (II) heat of hydrogenation orders.
(A) (i) (ii)
(iii) (iv)
(B) (i)
(ii)
(iii)
31. Among the following pairs identify the one which gives higher heat of hydrogenation :
(a) and (b) and
(c) CH3 – CH = CH – CH3 and CH3 – CH2 – CH = CH2 (d) and
32. Match each alkene with the appropriate heat of combustion:

Heats of combustion (kJ/mol) : 5293 ; 4658; 4650; 4638; 4632
(a) 1-Heptene
(b) 2,4-Dimethyl-1-pentene
(c) 2,4-Dimethyl-2-pentene
(d) 4,4-Dimethyl-2-pentene
(e) 2,4,4-Trimethyl-2-pentene
GOC
33. Write increasing order of heat of hydrogenation :
(i) (a) (b)
(ii) (a) (b)
(c) (d)
(iii) (a) (b)
(c) (d) (e)
(iv) (a) (b) (c)
(v) (a) (b) (c)
(HOH per  bond)
(vi) (a) (b)
(c) (HOH per benzene ring)
(vii) (a) (b)
(viii) (a) (b)
34. Give decreasing order of heat of combustion (HOC):
(i) (a) (b) (c)
(ii) (a) (b) (c)
(d)
(iii) (a) (b)
(iv) (a) (b) (c)
GOC
35. Arrange in order of C–H bond energy
a
H-CH2
d
H-CH-CH-C-CH3
c b
H e H H
CH2
f
H
36. Use the following data to answer the questions below:
H2
H = – 28.6 Kcal mol–1
Ni
excess H2
(Ni)

H = – 116.2 Kcal mol–1 Anthracene

Calculate the resonance energy of anthracene in kcal/mol.
37. Arrange the given phenols in their decreasing order of acidity:
(I) C6H5–OH (II) F OH (III) Cl OH (IV) O2N OH
Select the correct answer from the given code:

(A) IV > III > I > II (B) IV > II > III > I (C) IV > III > II > I (D) IV > I > III > II
38. Which one of the following is the most acidic?
(A) (B) (C) (D) CH2=CH–CH3
Acid & Base

39. Which one of the following phenols will show highest acidity?
CH3
CH3 H3C OH
H3 C OH OH
OH
(A) (B) O2N (C) (D)
H3 C NO2 H3C
CH3 CH3 NO2
NO2
40. Which of the following is weakest acid?
COOH COOH
COOH COOH
(A) (B) (C) (D) OH
OH OH
GOC
41. The correct pKa order of the follwoing acids is :
HO OH O HO OH
O O O O O O
(I) (II) (III)
(A) I > II > III (B) III > II > I (C) III > I > II (D) I > III > II
42. Arrange pH of the given compounds in decreasing order:

(1) Phenol (2) Ethyl alcohol
(3) Formic acid (4) Benzoic acid
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 4 > 3 (C)3 > 2 > 4 > 1 (D) 4 > 3 > 1 > 2
43. Consider the following compound :
OH
OH O2N NO2
O
O
OH
(A) (B) (C) CH3CCOOH (D)
COOH
O OH NO2
Which of the above compounds reacts with NaHCO3 giving CO2 ?

44. Match the column:
Column I Column II
(A) (P) Six  electrons
(B) (Q) Four  electrons
NH
(C) (R) Aromatic Compounds
N
H
H– N
(D) (S) Anti-aromatic compound
GOC

Column I Column II
(A) (P) Hybrid state of each atom sp2
(B) (Q) Anti aromatic
(C) (R) Delocalisation of  bond
(D) (S) Non aromatic
(T) Obeys Huckel's Rule for aromaticity
46. Match the column :

Column I Column II
(A) NH (P) Non aromatic
(B) (Q) Anti aromatic
(C) (R) Resonance

O
(D) (S) Aromatic

Column I Column II
+ +
(A) CH3OCH2 or CH2NHCH2
(P) First is more stable than second
+ +
(B) CH3OCH2CH2 or CH3OCH2
(Q) Second is more stable than first
(C) + or + (R) Not resonating structure of each other
+ +
CHCH3 CHCH3
(D) or (S) Resonance is present in both carbocation
GOC
Exercise - 3 | Subjective | JEE Advanced

ACIDS
1. Write the correct order of acidic strength of following compounds:
(i) (a) H–F (b) H–Cl (c) H–Br (d) H–I
(ii) (a) CH4 (b) NH3 (c) H2O (d) H–F
CH3
(iii) (a) CH3–CH2–O–H (b) CH 3  CH  O  H (c) CH3–C–O–H
|
CH 3 CH3
(iv) (a) F–CH2–CH2–O–H (b) NO2–CH2–CH2–O–H (c) Br–CH2–CH2–O–H

(d) NH 3  CH 2  CH 2  O  H
2. Write the correct order of acidic strength of following compounds:

(i) (a) CH3COOH (b) CH3CH2OH (c) C6H5OH (d) C6H5SO3H
(ii) (a) (b) (c)

COOH COOH COOH
COOH COOH CH2  COOH

(iii) (a) | (b) CH 2 (c) |
COOH COOH CH2  COOH
3. Write correct order of acidic strength of following compounds:
O O Cl O
(i) (a) Cl–CH2–C–O–H (b) Cl–CH2–C–O–H (c) Cl–C–C–O–H
Cl Cl
O O O
(ii) (a) CH3–CH2–CH–C–O–H (b) CH3–CH–CH 2–C–O–H (c) CH2–CH2–CH 2–C–O–H
F F F
O O O
|| || ||
(iii) (a) NO2  CH2  C  O  H (b) F  CH2  C  O  H (c) Ph  CH2  C  O  H
O
||
(d) CH3  CH2  C  O  H
O–H O–H O–H O–H O–H O–H

Cl
(i) (a) (b) (c) (ii) (a) (b) (c)
Cl
NO2 Cl CH3 Cl
O–H O–H O–H O–H
(iii) (a) (b) (c) (d)
GOC
O–H O–H O–H O–H

O
N
(i)(a) O (b) (c) (d)
O
N
O N
O O
O–H
O–H O–H O–H
O
N NO2 NO2 NO2
(ii) (a) (b) O (c) (d)
NO2
NO2 NO2
O O
C–O–H C–O–H
CH3
(i) (a) (b)
COOH COOH
Cl Br
(ii) (a) (b)
O
O O
C–O–H
C–O–H C–O–H
OMe
(iii) (a) (b) (c)
OMe OMe
O
C–O–H O O
C–O–H C–O–H
NO2
(iv)(a) (b) (c)
N NO 2
O O
GOC
7. Select the strongest acid in each of the following sets :
OH OH OH OH
(i) (a) (b) (c) (d)
CH3 NO2 Cl NH2
OH OH OH OH
(ii) (a) (b) (c) (d)

NO2 F CH3
OH OH OH OH
OMe
(iii) (a) (b) (c) (d)

OMe
OMe
8. Say which pka belong to which functional group in case of following amino acids :
COOH
(i) cysteine : HS 1.8, 8.3 & 10.8
NH2
COOH
(ii) glutamic acid : HO2C
NH2
: 2.19, 4.25, 9.67
9. Record the following sets of compounds according to increasing pKa ( = – log Ka)
OH OH
(a) , , cyclohexane carboxylic acid.
(b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid
(d) Phenol,o-nitrophenol, o-cresol
(e) Hexylamine, aniline, methylamine
10. Explain which is a stronger acid.

O O
(a) CH3CH3 BrCH2NO2 (b) CH3–C–CH 3 & CH3–C–CH2 CN
(c) CH3 – CHO CH3 – NO2
11. Explain which is a weaker acid.
OH OH OH OH SH OH
(a) or (c) or (b) or
O=C–CH3 O=C–CH3 CH3
GOC
12. Which of the following would you predict to be the stronger acid ?
O O
COOH
(a) or N C – OH
O
(b) CH3 – CH2 – CH2 – OH or CH3 – CH = CH – OH
(c) CH3 – CH = CH – CH2 – OH or CH3 – CH = CH – OH
Bases
13. Write increasing order of basic strength of following:
(i) (a) F  (b) Cl (c) Br  (d) I
(ii) (a) CH3 b) NH2 (c) OH (d) F 
(iii) (a) R–NH2 (b) Ph–NH2 (c) R–C–NH2
O
(iv) (a) NH3 (b) MeNH2
(c) Me2NH (d) Me3N (Gas phase)
(v) (a) NH3 (b) MeNH2
(c) Me2NH (d) Me3N (in H2O)

O
(i) (a) (b) (c)
NH NH N
Me
NH2 NH2
(ii) (a) (b) (c)

NH
N N N
(iii) (a) (b) (c)
O2N Me F
NH2 NH2
NH2 NH2
(iv) (a) (b) (c) (d)


NH3 Cl CH 3 H
    
(i) (a) CH3–CH2– NH2 (b) CH3 – CH = N H (c) CH3 – C  N
.. .. ..
(ii) (a) CH3–C–NH 2 (b) CH3 – CH2 – NH2 (c) CH3–C–NH 2 (d) NH2–C–NH2
O NH
.. NH
..
NH2
(iii) (a) (b) (c)

N N
GOC
O
NH2 NH–CH2–CH3
NH – C – CH3
(iv) (a) (b) (c)
NH2 NH2
Me Me
(v) (a) (b) Me Me

N N
O O O O
NH2 NH2 NH2 NH2
(i) (a) (b) (c) (d)

NO2 CN OMe NH2
NH2
NH2
NH2 H
C H H
(ii) (a) (b) (c)
H C H
C
H H
H
H
NH2
NH2
NH2
NO2
(iii) (a) (b) (c)
NO2 NO2
NH2 NH2 H NH2

C H
(iv) (a) (b) (c)
H
NMe2 Me Me
NMe2
N
OMe
(v) (a) (b) (c)
OMe OMe
GOC
17. Select the strongest base in following compound :

O S
(i) (a) (b) (c) (d)
N N
N N
H H H
NH2
(ii) (a) (b) (c) (d) N

NH
N
H
N
(iii) (a) (b) (c) (d)
N N N
N
H CH3 H
H
H H Me
+
N¯Li
N N N
(iv) (a) (b) (c) (d)
18. Arrange the following compound in decreasing order of their basicity.

(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC  CNa
NH2 C – NH2
(ii) (a) NH2 (b) CH2 – NH2 (c) (d)
NO2 O
(iii) (a) HO¯ (b) NH3 (c) H2O
19. Basicity order in following compound is :
CH3 CH3
O
Nb
H2 N – C– CH2 CH2 – NH – C – CH3
c
NH
a
N
CH3 d CH3
(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
20. Consider the following bases:

(I) o-nitroaniline (II) m-nitroaniline (III) p-nitroaniline
The decreasing order of basicity is:
(A) II > III > I (B) II > I > III (C) I > II >III (D) I > III > II
21. Consider the basicity of the following aromatic amines:

(I) aniline (II) p-nitroaniline (III) p-methoxyaniline (IV) p-methylaniline
The correct order of decreasing basicity is:
(A) III > IV > I > II (B) III > IV > II > I (C) I > II > III > IV (D) IV > III > II > I
GOC
22. Which one of the following is least basic in character?
(A) N (B) N N–H (C) N (D) N

H H H
23. In each of the following pair of compounds, which is more basic in aqueous solution? Give an explanation for your
choice:
NH
(a) CH3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2

(c) n-PrNH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl-N,N-dimethylaniline
(e) m-nitroaniline or p-nitroaniline
24. From the following pair, select the stronger base:

(a) p-methoxy aniline or p-cyanoaniline (b) pyridine or pyrrole
(c) CH3CN or CH3CH2NH2
25. Explain which compound is the weaker base.

NH2 NH2
(a) or (b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–
NO2
OH OH
O O O O
CH2 CF3
(c) O––C–C–OH or HO–C–C–OH (d) or
26. Rank the following amines in increasing basic nature.

NH2 NH2 NH2 NH2
CH 3 NO2
(a)
(i) (ii) (iii) (iv)

NH2
NH 2 NH2
CH 3
(b)
CH 3 CH3
(i) (ii) (iii) (iv)
27. Arrange the basic strength of the following compounds.

(a) OH– CH3COO– Cl–
(i) (ii) (iii)
(b) CH  C– CH2 = CH– CH3CH2–
(i) (ii) (iii)
(c) (i) CH2 = CHCH2NH2
(ii) CH3CH2CH2NH2
(iii) CH  C – CH2NH2
GOC
28. Arrange the basic strength of the following compounds.
NH2 NH–C6 H5 NH2
(a)
(i) (ii) (iii)
NH2
NH2 NH 2
Cl
(b)
Cl Cl
(i) (ii) (iii)

NH2 NH2 NH2
(c)
H3C O2N
(i) (ii) (iii)
29. Arrange the following compounds in order of increasing basicity.

(a) CH3NH2, CH3 NH 3 , CH3NH— (b) CH3O—, CH3NH—, CH3 CH2
(c) CH3CH = CH—, CH3CH2 CH2 , CH3CC—
30. Rank the amines in each set in order of increasing basicity.
H
NH2 NH2 N
(a
H
H N
N N
(b)
H H H
N N N N
(c)
7 6
5
4 5 N 5 N
4 6 1
8
31. N N–H 2
N N 1 3 9N 4
N
1 3 3
2 2
H
Pyrimidine Imidazole Purine

Among the following which statement(s) is/are ture:
(A) Both N of pyrimidine are of same basic strength
(B) In imidazole protonation takes places on N–1.
(C) Purine has 3 basic N.
(D) Pyrimidine imidazole and purine all are aromatic
GOC
Exercise - 4 | Level-I Previous Year | JEE Main

1. Amongst the following the most basic compound is - [AIEEE-2005]
(A) aniline (B) benzylamine (C) p–nitroaniline (D) acetanilide
2. The number and type of bonds between two carbon atoms in calcium carbide are [AIEEE 2005]
(A) two sigma, two pi (B) two sigma, one pi (C) one sigma, two pi (D) one sigma, one pi
3. Due to the presence of an unpaired electron, free radicals are [AIEEE 2005]
(A) cations (B) anions (C) chemically inactive (D) chemically reactive
4. Among the following acids which has the lowest PKa value ? [AIEEE 2005]
(A) CH3CH2COOH (B) (CH2)2 CH – COOH
(C) HCOOH (D) CH3COOH
5. The increasing order of stability of the following free radicals is - [AIEEE 2006]
  
(A) (C6H5)3 C < (C6H5)2 C H < (CH3)3 C < (CH3)2 C H
   
(B) (C6H5)2 C H < (C6H5)3 C < (CH3)3 C < (CH3)2 C H
   
(C) (CH3)2 C H < (CH3)3 C < (C6H5)3 C < (C6H5)2 C H
   
(D) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3 C
6. The correct order of increasing acid strength of the compound is : [AIEEE 2006]
Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO2H is
Me
(A) d < a < c < b (B) d < a < b < c (C) a < d < c < b (D) b < d < a < c
7. Which one of the following is the strongest base in aqueous solution ? [AIEEE-2007]
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
8. Presence of a nitro group in a benzene ring : [AIEEE 2007]

(A) activates the ring towards electrophilic substitution
(B) renders the ring basic
(C) deactivates the ring towards nucleophilic substitution
(D) deactivates the ring towards electrophilic substitution
9. Arrange the carbanions, (CH3)3 C , C Cl 3 , (CH3)2 C H , C6H5 C H 2 , in order of their decreasing stability -
(A) (CH3)2 C H > C Cl 3 > C6H5 C H 2 > (CH3)3 C [AIEEE 2009]
(B) C Cl 3 > C6H5 C H 2 > (CH3)2 C H > (CH3)3 C
(C) (CH3)3 C > (CH3)2 C H >C6H5 C H 2 > C Cl 3
(D) C6H5 C H 2 > C Cl 3 > (CH3)3 C > (CH3)2 C H
GOC
10. The correct order of increasing basicity of the given conjugate bases (R = CH3) is [AIEEE 2010]
–
(A) RCOO  HC  C  R  N H2 (B) R  HC  C  RCOO  N H2
(C) RCOO  NH2  HC  C  R– (D) RCOO  HC  C  N H2  R
11. The correct order of acid strength of the following compounds is : [AIEEE 2011]
A. Phenol B. p-Cresol C. m-Nitrophenol D. p-Nitrophenol
(A) D > C > A >B (B) B > D > A > C (C) A > B > D >C (D) C > B > A > D
12. The non aromatic compound among the following is - [AIEEE 2011]
(A) (B) (C) (D)

S
13. The order of stability of the following carbocations: [JEE Main 2013]
CH2
(I) CH2= CH – CH2 (II) CH3–CH2– CH2 (III) is :
(A) I > II > III (B) III > I > II (C) III > II > I (D) II > III > I
14. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value?
(A) CH3NH2 (B) (CH3)3N (C) C6H5NH2 (D) (CH3)2NH [JEE Main 2014]
15. Which of the following molecules is least resonance stabilized ? [JEE Main 2017]
(A) (B) N (C) (D)

O
O
16. The increasing order of basicity of the following compounds is : [JEE Main 2018]
NH2
(a) NH2 (b) NH (c) (d) NHCH3
NH
(A) (b) < (a) < (d) < (c) (B) (d) < (b) < (a) < (c)
(C) (a) < (b) < (c) < (d) (D) (b) < (a) < (c) < (d)
17. The predominant form of histamine present in human blood is (pKa, Histidine = 6.0) [JEE Main 2018]
H H
N
N
(A) (B) NH3
N NH2
H N
H H
N N
NH3
(C) NH2 (D)
N
N H
18. Which of the following compounds will show the maximum 'enol' content ? [JEE Main 2019]
(A) CH3COCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2
19. Which amongst the following is the strongest acid ? [JEE Main 2019]
(A) CHBr3 (B) CHI3 (C) CHCl3 (D) CH(CN)3
GOC
20. The correct order for acid strength of compounds : [JEE Main 2019]
CH  CH, CH3 – C  CH and CH2 = CH2 is as follows :
(A) CH3 – C  CH > CH2 = CH2 > HC  CH
(B) CH3 – C  CH > CH  CH > CH2 = CH2
(C) HC  CH > CH3 – C  CH > CH2 = CH2
(D) CH  CH > CH2 = CH2 > CH3 – C  CH
21. Arrange the following labelled hydrogens in decreasing order of acidity : [JEE Main 2020]
(A) b > c > d > a (B) c > b > a > d (C) b > a > c > d (D) c > b > d > a
22. If you spill a chemical toilet cleaning liquid on your hand, your first aid would be: [JEE Main 2020]
(A) vinegar (B) aqueous NaOH (C) aqueous NaHCO3 (D) aqueous NH3
23. Which one of the following compounds possesses the most acidic hydrogen ? [JEE Main 2020]
(A) H3C – C  C – H (B)
(C) (D)
24. Consider the following molecules and statements related to them : [JEE Main 2020]
(A) (B)
(a) (B) is more likely to be crystalline than (A)

(b) (B) has higher boiling point than (A)
(c) (B) dissolves more readily than (A) in water
Identify the correct option from below :
(A) only (a) is true (B) (a) and (b) are true
(C) (b) and (c) are true (D) (a) and (c) are true
25. The decreasing order of reactivity of the following organic molecules towards AgNO3 solution is :
(A) (C) > (D) > (A) > (B) (B) (A) > (B) > (C) > (D) [JEE Main 2020]
(C) (B) > (A) > (C) >(D) (D) (A) > (B) > (D) > (C)
GOC
26. Among the following compounds, which one has the shortest C-Cl bond ? [JEE Main 2020]
(A) (B) (C) (D) H3C – Cl
27. Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily ?
[JEE Main 2020]
(A) (B) (C) (D)
28. The increasing order of basicity of the following compounds is : [JEE Main 2020]
(A) (B) < (A) < (C) < (D) (B) (A) < (B) < (C) < (D)
(C) (D) < (A) < (B) < (C) (D) (B) < (A) < (D) < (C)
29. The increasing order of the acidity of the -hydrogen of the following compounds is : [JEE Main 2020]
(A) (C) < (A) < (B) < (D) (B) (B) < (C) < (A) < (D)
(C) (A) < (C) < (D) < (B) (D) (D) < (C) < (A) < (B)
30. The increasing order of boiling points of the following compounds is : [JEE Main 2020]
OH OH OH OH
CH3 NO2 NH2 OCH3

I II III IV
(A) I < IV < III < II (B) IV < I < II < III (C) I < III < IV < II (D) III < I < II < IV
GOC
31. The increasing order of pKb values of the following compounds is : [JEE Main 2020]
N(CH3) 2
N(CH3) 2 NHCH3 NHCH3
(I) (II) (III) (IV)

CN OH
OCH3
(A) II < I < III < IV (B) II < IV < III < I (C) I < II < IV < III (D) I < II < III < IV
32. Which one of the following compounds is non-aromatic ? [JEE-Mains (24-Feb_Shift -2)2021]
(A) (B) (C) (D)

O
33. The correct order of acid character of the following compounds is :
[JEE-Mains (25-Feb_Shift -2)2021]
(A) II>III>IV>I (B) III>II>I>IV (C) IV>III>II>I (D) I>II>III>IV
34. A. Phenyl methanamine B. N, N-Dimethylaniline [JEE-Mains (26-Feb_Shift -2)2021]

C. N-Methyl aniline D. Benzenamine
Choose the correct order of basic nature of the above amines.
(A) D > C > B > A (B) D > B > C > A
(C) A > C > B > D (D) A > B > C > D
35. In the following molecule, [JEE-Mains (18-March_Shift -1)2021]

a
H3 C
b c
C=C–O
H H
Hybridisation of Carbon a, b and c respectively are :

(A) sp3, sp2, sp2 (B) sp3, sp2, sp (C) sp3, sp, sp (D) sp3, sp, sp2
36. Among the following, the aromatic compounds are: [JEE-Mains (16-March_Shift -1)2021]
(A) (B) (C) (D)
Choose the correct answer from the following options:

(A) (A) and (B) only (B) (A), (B) and (C) only
(C) (B), (C) and (D) only (D) (B) and (C) only
GOC
37. Assertion A :Enol form acetone [CH3COCH3] exists in <0.1% quantity. However, the enol form the acetyl
acetone [CH3COCH2OCCH3] exists in approximately 15% quantity.
Reason R: Enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding, which is not possible
in enol form of acetone. [JEE-Mains (16-March_Shift -1)2021]
Choose the correct statement:
(A) A is true but R is false
(B) Both A and R are true but R is the correct explanation of A
(C) A is false but R is true
(D) Both A and R are true but R is not the correct explanation of A
38. The INCORRECT statement regarding the structure of C60 is: [JEE-Mains (16-March_Shift -2)2021]
(A) It contains 12 six-membered rings and 24 five-membered rings.
(B) Each carbon atom forms three sigma bonds.
(C) The five-membered rings are fused only to six-membered rings.
(D) The six-membered rings are fused to both six and five-membered rings.
39. Statement-I: Sodium hydride can be used as an oxidising agent.

Statement-II: The lone pair of electrons on nitrogen in pyridine makes it basic:
Choose the CORRECT answer from the options given below:
(A) Statement I is true but statement II is false [JEE-Mains (16-March_Shift -2)2021]
(B) Both statement I and statement II are false
(C) Both statement I and statement II are true
(D) Statement I is false but statement II is true
40. Which of the following is least basic? [JEE-Mains (16-March_Shift -2)2021]

••
(A) (CH3CO)2 •• (B) (CH3CO) N H C2H5
NH
(C) (C2H5)3 •• (D) (C2H5)2 ••
N NH
41. Which of the following is an aromatic compound ? [JEE-Mains (17-March_Shift -1)2021]


–
(A) – (B) (C) (D)
–
GOC
Exercise - 4 | Level-II Previous Year | JEE Advanced
1. For 1-Methoxy-1,3-butadiene, which of the following resonating structure is the least stable ? [IIT-2005]
(A) H2C – CH – CH = CH – O – CH 3 (B) H2C – CH = CH – CH = O – CH 3
(C) H2C = CH = CH – CH – O – CH 3 (D) H2C = CH – CH – CH = O – CH 3
2. Predict whether the following molecules are iso structural or not. Justify your answer. [IIT-2005]
(i) NMe3 (ii) N(SiMe3)3
3. When benzene sulfonic acid and p-nitrophenol are treated with NaHCO3, the gases released respectively are
(A) SO2,NO2 (B) SO2,NO (C) SO2,CO2 (D) CO2,CO2 [IIT-2006]
4. (I) 1, 2-dihydroxy beznene (II) 1, 3-dihydroxy benzene

(III) 1, 4-dihydroxy benzene (IV) Hydroxy benzene
The increasing order of boiling points of above mentioned alcohols is [IIT-2006]
(A) I < II < III < IV (B) I < II < IV < III (C) IV < I < II < III (D) IV < II < I < III
5. Among the following, the least stable resonance structure is : [IIT-2007]
O O
O O N N
(A) N (B) N (C) (D)
O O
O O
6. Statement-1: p-Hydroxybenzoic acid has a lower boiling point then o-hydroxybenzoic acid. [IIT-2007]
Statement-2: o-Hydroxybenzoic acid has a intramoleculer hydrogen bonding.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for statement-1.
(C) Statement1 is true, statement-2 is false.
(D) Statement1 is false, statement-2 is true.
7. Hyperconjugation involves overlap of the following orbitals [IIT-2008]

(A)  –  (B)  – p (C) p – p (D)  – 
8. The correct stability order for the following species is [IIT-2008]
(I) (II) (III) (IV)

O O
(A) II > IV > I > III (B) I > II > III > IV (C) II > I > IV > III (D) I > III > II > IV
GOC
9. The correct acidity order of the following is [IIT-2009]
COOH
OH OH COOH
(I) (II) (III) (IV)
CH3
Cl
(A) III > IV > II > I (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I
10. The correct stability order of the following resonance structures is [IIT-2009]
+ – + – – + – +
(I) H2C = N = N (II) H2C – N = N (III) H2C – N = N (IV) H2C – N = N
(A) I > II > IV > III (B) I > III > II > IV (C) II > I > III > IV (D) III > I > IV > II
11. In the following carbocation; H/CH3 that is most likely to migrate to the positively charged carbon is
[IIT-2009]
H H
1 2 + 4 5
H3C – C – C – C –CH3
3
OH H CH3
(A) CH3 at C-4 (B) H at C-4 (C) CH3 at C-2 (D) H at C-2
12. The total number of basic group in the following form of lysine is : [IIT-2010]
O
+
NH3 – CH2 – CH2 – CH2 – CH2 – CH – C
–
O
NH2
13. Amongst the following, the total number of compounds soluble in aqueous NaOH is [IIT-2010]
H3C CH3
N COOH NO2 OH
N
H3C CH 3
14. Among the following compounds, the most acidic is: [IIT-2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
15. The total number of contrubting structure showing hyperconjugation (involving C-H bonds) for the following
carbocation is [JEE-2011]
CH3 CH2CH3
GOC
16. In Allen (C3H4), the type (s) of hybridisation of the carbon atoms is (are) [JEE Adv. 2012]
(A) sp and sp3 (B) sp and sp2 (C) only sp2 (D) sp2 and sp3
17. Which of the following molecules in pure from is (are) unstable at room temperature [JEE Adv. 2012]
O O
(A) (B) (C) (D)
18. The compound that does NOT liberate CO2, on treatment with aqueous solium bicarbonate solution is
(A) Benzoic acid (B) Benzenesulphonic acid [JEE Adv. 2013]
(C) Salicylic acid (D) Carbolic acid (Phenol)
19. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to [JEE Adv. 2013]
(A)   p (empty) and    electron delocalisations
(B)    and    electron delocalisations
(C)   p (filled) and    electron delocalisations
(D) p (filled)  and    electron delocalisations
20. The number of resonance structures for N is : [JEE Adv. 2015]

OH
NaOH
N
21. The correct order of acidity for the following compounds is : [JEE Adv. 2016]
CO2H
CO2H
CO2H CO2H
HO OH OH
(I) (II) (III) (IV)
OH
OH
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
22. Among the following the number of aromatic compound(s) is : [JEE Adv. 2017]
GOC
23. The order of basicity among the following compounds is : [JEE Adv. 2017]
NH NH2
(I) (II) N NH (III) HN N (IV)
H3C NH 2 H 2N NH
(A) IV > II > III > I (B) II > I > IV > III (C) I > IV > III > II (D) IV > I > II > III
24. The correct order of acid strength of the following carboxylic acids is : [JEE Adv. 2019]
O
O H O
OH OH
I. H II. III. MeO IV. H3C
OH O
OH H
(A) II > I > IV > III (B) III > II > I > IV (C) I > II > III > IV (D) I > III > II > IV
47. With respect to the compounds I–V, choose the correct statement(s). [JEE Advance 2020]
(A) The acidity of compound I is due to delocalization in the conjugate base.

(B) The conjugate base of compound IV is aromatic.
(C) Compound II becomes more acidic, when it has a –NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.
48. Consider the following four compounds I, II, III, and IV. [JEE Advance 2020]
I II III IV
Choose the correct statement(s).
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV
(D) Steric effect makes compound IV more basic than III.
GOC
1. A 2. C 3. A 4. C 5. B 6. A 7. B
8. A 9. C 10. D 11. B 12. C 13. C 14. B
15. A 16. A 17. C 18. C 19. D 20. C 21. D
22. C 23. D 24. C 25. C 26. A 27. C 28. B
29. C 30. D
Exercise - 2 (Level-I) Objective Problems | JEE Main
1 A 2 A 3 C 4 B 5 A 6 A 7 C
8 D 9 D 10 D 11 B 12 B 13 B 14 B
15 B 16 C 17 A 18 D 19 C 20 B 21 B
22 B 23 D 24 C 25 C 26 A 27 B 28 C
29 C 30 C 31 B
Exercise - 2 (Level-II) Multiple Correct | JEE Advanced

1. (a), (c), (d), (g), (j), (l), (m) 2. (a), (b) 3. (a), (b), (c), (f)
4. a = Resonance form, b = A, c = C, d = A & B, e = B & C, f = 0, g = B, h = B
5. 6 (i, ii, iii, vi, vii, ix)
6. (a) I, (b) I, (c) I, (d) II, (e) II
O O O
7. (a) II, (b) II, (c) II, CH3 – C – CH – CH = C – CH3 (d) II, CH3–CH=CH – CH = N
O
NH 2
(e) II, CH3 – CH 2 – C – NH 2
8. (a) II, (b) I, (c) I, (d) I, (e) I 9. (a) II, (b) I, (c) I, (d) II
10. (a) II, (b) I, (c) II, (d) II, (e) II 11. A 12. A
13. B 14. B 15. C 16. A
17. A 18. A 19. ABD 20. ABC
21. (i) c > b > a (ii) c > b > a (iii) b > c > a (iv) c > b > a
(v) c > b > a (vi) b > c > a (vii) a > b > c (viii) a > b > c
(ix) a > c > b (x) d > c > b > a (xi) a > b > c (xii) c > b > a
22. (i) b > c > a (ii) b > c > a > d (iii) c > a > b (iv) a < b
(v) a > b (vi) a > b > c (vii) a > b > c (viii) a > b > c
(ix) a > b (x) c > b > a > d (xi) a > c > b (xii) c > a > b (xiii) a > b > c > d
GOC
23. (a) II, (b) I, (c) I, (d) I, (e) II

24. (a) I, (b) I, (c) II (d) I (e) I (f) I
25. iii > ii > i 26. C 27. (a) i, (b) i, (c) ii 28. A
29. (a) (i) D > C > B > A (ii) E > C > D > B > A (b) 2 > 1 (c) 2 < 1 (d) 1 < 2 (e) 1 > 2
30. (A) (I) iv > iii > ii > i, (II) i > ii > iii > iv (B) (I) iii > ii > i (II) i > ii > iii
31. (a) I, (b) I, (c) II, (d) I
32. (a) 4658, (b) 4638, (c) 4632, (d) 4656 (e) 5293
33. (i) b > a (ii) a > b > c > d (iii) a > b > c > d > e (iv) b > c > a
(v) a > b > c (vi) a > b > c (vii) b > a (viii) b > a
34. (i) c > b > a (ii) a > b > c > d (iii) a > b (iv) c > b > a
35. d<f<b<c<a<e
On the basis of stability of free radical formed after removal of H .
36. Anthracene is 14 p e's system
i.e. there are 7 p bonds
Expected (theoretical) heat of hydrogen = – 28.6×7 = – 200.2 kcal/mol
Observed (experimental) heat of hydrogen = –116.2
R. E. = – 166.2 – (–200.2)
= 84 kcal/mol
37. C 38. B 39. C 40. B 41. B 42. B 43. ABCD
44. (A) P, R; (B) Q, S; (c) P, R; (D) P, R
45. (A) P, R, T; (B) P, R, S (C) S ; (D) P, Q, R
46. (A) P, R; (B) P, R; (C) R, S; (D) P, R
47. (A) Q, R, S; (B) Q, R; (C) P, R; (D) P, R
Exercise - 3 | Subjective | JEE Advanced
1. (i) d > c > b > a (ii) d > c > b > a (iii) a > b > c (iv) d > b > a > c
2. (i) d > a > c> b (ii) c > b > a (iii) a > b > c
3. (i) c > b > a (ii) a > b > c (iii) a > b > c > d
4. (i) a > b > c (ii) a > b > c (iii) d > b > c > a
5. (i) c > a > b > d (ii) d > c > a > b
6. (i) b > a (ii) b > a (iii) c > b > a (iv) c > a > b
7. (i) b (ii) a (iii) b
COOH HO2C COOH

1.8 4.25 2.19
8. (i) cysteine : HS
8.3 (ii) glutamic acid :
NH 2 NH2
10.8 9.67
GOC
9. (a) 3 < 2 < 1; (b) 1 < 2 < 3; (c) 3 < 2 < 1; (d) 2 < 1 < 3; (e) 2 < 3 < 1
10. (a) 2; (b) 2; (c) 2 11. (a) 2; (b) 2; (c) 2 12. (a) 2; (b) 2; (c) 2
13. (i) a > b > c > d (ii) a > b > c> d (iii) a > b > c (iv) a < b < c < d (v) c > b> d> a
14. (i) a < b < c (ii) c > a > b (iii) b > c > a (iv) c > d > b > a
15. (i) a > b > c (ii) d > c > b > a (iii) b > c > a (iv) c > b > a (v) b > a
16. (i) d > c > b > a (ii) c > b > a (iii) b > a > c (iv) a > b > c (v) c > a > b
17. (i) d (ii) b (iii) a (iv) a
18. (i) b > a > d > c (ii) b > a > c > d (iii) a > b > c
19. B 20. A 21. A 22. A
23. (a) i, (b) ii, (c) i, (d) ii, (e) i 24. (a) i, (b) i, (c) ii
25. (a) 2; (b) 1; (c) 2; (d) 2
26. (a) 3 < 2 < 1 < 4; (b) 1 < 2 < 3 < 4 27. (a) 1 > 2 > 3; (b) 1 < 2 < 3; (c) 3 < 1 < 2
28. (a) 2 < 1 < 3; (b) 1 < 2 < 3; (c) 2 > 1 > 3 29. (a) 2 < 1 < 3; (b) 1 < 2 < 3; (c) 3 < 1 < 2
30. (a) 2 > 1> 3, (b) 1 > 2 > 3, (c) 1 > 3 > 2, 31. A, B, C, D
Exercise - 4 | Level-I Previous Year | JEE Main

1. B 2. C 3. D 4. C 5. D 6. B 7. C
8. D 9. B 10. D 11. A 12. D 13.. B 14. D
15. C 16. A 17. B 18. B 19. D 20. C 21. A
22. C 23. C 24. B 25. C 26. B 27. A 28. D
29. D 30. A 31. C 32. B 33. A 34. D 35. A
36. D 37. B 38. A 39. D 40. A 41. A
Exercise - 4 | Level-II Previous Year | JEE Advanced

1. C
SiMe3
N N
2. Me Me SiMe3 SiMe3
Me
(Pyramidical)
Given componds are not isostrucutral

Delocalised of l.p. of nitrogen in vacant d-orbital of silicon makes compound planar.
3. D 4. C 5. A 6. D 7. B 8. D 9. A
10. B 11. D 12. 2 13. 4 14. C 15. 6 16. B
17. B 18. D 19. A 20. 9 21. A 22. 5 23. D
24. C 25. ABC 26. CD
GOC GOC

1. A
Bond Formation is-
(A) Always exothermic
In Bond formation heat always release.
2. C
CH2=CH–CN CH2=CH–C N
3 2 1
sp2 sp
(C) sp2 – sp overlap
3. A
sp
3
CH3–CH=CH–CH=C=CH–C C–CH3 sp
3 2 2 2 2
sp sp sp sp sp sp sp
4. C
1 H
H
H H
5
H H 19 Bond
H H
5. B
O O O O
In entire system resonance is present
6. A
Due to electronegativity difference the bond are polarized so option (a) is apply. [implies the
atom’s ability to cause bond polarization]
7. B
CH3 CH 3
CH3 CH3 CH 3 CH3 CH 3 CH3
< <
1-CH3 2-CH3 3-CH3

group group group
3CH3 group apply inductive effect
Join with code “SKSIRLIVE” for 10% discount on your unacademy subscription. Page 79
GOC
8. A
CH3 CH 3
CH3 C CH2–CH3 > CH3 –C– > CH3 CH CH2 > CH3–CH2–CH2 > CH3
2-CH 3 CH 3 CH2–CH3
1-CH 2 3-CH3
Alkyl group increase the +I effect because it is increase the electron donating power to the
group.
9. (i) CH3—CH2 (ii) CH2=CH2 (iii) CH2 C
3 2
sp sp sp (more E.N.)
(less E.N.)
Stability order iii > ii > i

10. D
O O
H H H
F F –I
stabilize by more E.N. group
Acidic strength  – m, –H, –I

So –I strength is apply here so acidic strength increase here.
11. B
Cl–CH2–COOH < CH3 COOH < CH3–CH2–COOH
–I +I +I
I
PH value  effect
–I
12. C
Cl CH2–COOH Br CH2–COOH
low-I lowest-I
NO2 CH2–COOH CN CH2–COOH
high-I medium-I
I
Pka 
–I
Lowest Pka value is Nitro acetic acid.
GOC
13. C
–I 2 1
(a) F–CH2CH2COOH F –CH2–CH2–COO
–I 2 1
(b) Cl–CH–CH2–COOH Cl –CH–CH2–COO
| |
Cl Cl
–I 1
(c) F–CH2–COOH F –CH2–COO
less distance
more acidic
2 1
(d) Br–CH2–CH2–COOH Br –CH2–CH2–COO
–I
1
acidity  Ka   Pkb
PKa
acidity order = c > b > a > d
Pkb order = c > b > a > d
14. B
+I
(A) CH3—COOH CH3—C—O
||
O
+I
..
(B) MeO CH2 COOH Me—O
.. —CH2—COO
F
|
(C) CF3COOH F—C—COO
|
F –I
Me Me
(D) —COOH —COO
Me Me
+I
Acid strength
order :- d<a<b<c
15. A
CH3 +I
NH3 < CH3 NH2 < NH
CH 3 +I
Basic nature  + effect [+m, +H, +I]
16. A
CH 3–CH 2 NH2 > CH 2=CH–NH2 > CH=C–NH 2
sp2 sp
basic nature  + effect [+m, +H, +I]
basic nature sp3 > sp2 > sp
More E.N. so e– withdraw easy so decrease the basic strength.
GOC
17. C
..
CH 3—N—CH 3
(A) Tri methyl amine  |
CH3
NH2
(B) aniline =
..
(C) Di methyl amine = CH 3—NH —CH3
More electron density on 'N' more Basicity (it is more basic than 3° amine because 3° amine is
sterically hindered)
(D) Methyl Amine = CH3—NH2
18. C
Coplanar = carbon should have sp3 hybridised.
sp3
(C)
19. D
CH2=CH–CH=CH2 CH2–CH=CH–CH2
CH2–CH=CH–CH2
All are canonical structures.
20. C
l m plete
ra inco
ut e t is
O ne O
o c t
O
C C C octet is completed
H OH H OH H OH
(1) > (3) > (2)
(1) Neutral structure are more stable as compare to charged structure.

(3) All the atom have octet is completed so more stable structure.
(2) Octet is incompleted so least stable both the structure.
21. D
IV str. is least stable CH 2=CH–CH–CH–OCH 3 due to repulsion b/w & l.p..
22. C
OH
(C) Neutral specie is most stable.
23. D
O–N N=O Complete octet & Extended conjugation
GOC
24. A
N N N N N
(I) (II) (III) (IV) (V)

(I = V) > (II > IV) > III
Neutral Opposite Opposite charge at
charge more distance.
nearest
25. C
N N N N N
| | | | |
H H H H H
(I) (II) (III) (IV) (V)
(I) > III = IV > II = V

Opposite opposite
charge charge
near have more
distance
26. A
m effect is the delocalization of electron. In this effect only l.p. and  bond are participated.
27. C
–Cl
–Cl have l.p so it can donate e–so its show +m effect also but it is E.N species so its behave as e–
withdrawing species so –I effect also show in case of halogen –I is more dominate as compare to
+m effect.
28. B
O–H O–H O–H O–H O–H
O
O
m m
p
OH increase the electron density on ortho and para position.
29. C
O O +m +m O
N O–H O O C –m
more
e – so
e–
donate
withdrawing
maximum
(A) (B)
NO2 behave as
e– withdrawing
species
So option (C).
30. D
NO2
NO2
(NO2) apply –I effect and its occur at two places so its withdrawing the e– into the ring so  e–
density is minimum.
GOC
Exercise - 2 Level - 1 | JEE Main

1. A
. .
C6H5–CH –C6H5 C6H 5–CH–CH=CH 2
(I) (II)
more R.S. Reso. + hyper conj.
. .
CH3–CH –CH3 C6H 5–CH –CH3
(III) (IV)
(2) + I group R.S.
.
(V) CH3–CH–CH–CH2–CH 2
(1) + I group
.
(VI) CH3–CH2–C–CH3
|
CH3
(3) + I group
(A) I > II > IV > VI > III > V
2. A
H
H .
. .
(I) (II) (III) (IV)
.
H H
H H H H
H .
H .
+
less
resonance
H
.
H
more
resonance
(A) III > II > I > IV
3. C
1 H
(A) H=4 (B)
2 H=2
3
H=8 H
(C) (D)
stability of carbocation  no. of –H.
Option C have 8H so highest stability of carbocation.
GOC
4. B
CH3
C CH3
CMe3
CH3 CH 3
CH3 CH3
(I) No alpha hydrogen (II)
CH3
+
C CH 3 CHC3
CH3
CH 3
Me
H
Me
(III) (IV)
III > II > I > IV Bredt rule
5. A
(I) (II) (III)
Extended Cross
conjugation conjugation
6. A
O
(A) CH3 CH CH 3 Most Stable
+
–
non-bonding e Bonding
+ CH 3
(B) CH 3 CH
+
(C) CH 3 CH CH3
CH 3
+
(D) CH3 —C
CH 3
GOC
7. A


(1) Me  C H2 is more stable than MeO  C H2
it is false because Me–O–CH2 Me–O=CH2

6e– 8e–
By Resonance stablized
 
So MeO  C H2 is more stable than Me  C H2
So statement (1) is False.
(2) Me is a +I group where as Me–O is a –I group.
8. D
(A) O Br O Br
..
..
(B) O
.. O
Br Br
..
N Br N Br
(C) | |
Ph Ph -I
..
N Br N Br
(D) | |
CH3 CH3 +I
Hyperconjugation
(stable)
9. D
O O
N or N
O
2(–I groups are here)
So – ve ion stable.
10. D
3
sp
(I) CH3—CH2 (II)

+I
3
sp
2 2
sp sp
(III) (III)
2 3
sp sp
(D) III > IV > I > II
GOC
11. B
CH2
Cl —C— Cl > > CH 3—CH—CH3 > CH3—C—CH3
|
|
Cl +I groups CH3
-I groups
+I groups
12. B
1 1 1
2 2 2
3 3 3
4 4 4
C1 — C2 Bond has double Bond in two structure so short Bond length

C2 — C3 Bond has single Bond in 2 structure.
(B) So C1 — C2 Bond is shorter than C2 — C3 Bond.
13. (B)
O O
Longest C — O Bond.
14. (B)
C2H6 > C6H6 > C2H4 > C2H2
H3C — CH 3 H2C = CH2 HC  CH
Pure single Partial Triple Bond

Bond double
15. B
+ I effect of o– is maximum so e–
density maximum in ring
16. (C)
4 e
no conjugation
2 e
(2)
(4n + 2) e heckles rule
4n e
4x1 e (4x0 + 2) = 2 e
(I)
4 e Aromatic
non aromatic
antiaromatic
GOC
17. (A)
(I) (II) (III)

 4e– (4n + 2)e– (4n + 2)e–
 4×1e– (4×0+2)e–  (4 + 2)e–
 4e–  2e–  6e–
Anti Aromatic aromatic aromatic
18. (D)
O O
O
O O O O
6 e
–
–
O 8 e
–
6 e 6 e–
aromatic anti aromatic
aromatic aromatic
19. (C) N=N N N
Aromatic + opposite charge nearest
20. B
(B) aromatic
O
O
aromatic
Both are aromatic

21. B
Aro.
Aro.
(I) (II) (III) 7eqt. st.
+5eqt.st.
most stable
more Rotational
Aro. Aro. energy.
Aro. Anti Aro.
unstable
least Rotation energy
GOC
22. B
(A) (B) (C) (D)

–
2 e – 4 e 6 e– –
6 e
aromatic anti aromatic aromatic
aromatic
So option (B) is anti-aromatic and remain option are aromatic so odd species is option (B).
23. (D)
N N
N N–H
8 e
–
8 e–
anti aromatic anti aromatic
(A) (B)
N–H
N–H N–H
–
– 6 e
8 e
aromatic
anti aromatic
(C) (D)
Option (D) have hetrocyclic compound with have aromatic character.
24. (C)
CH3 CH3
CH 3
HO OH HO OH
HO
HO OH HO + OH
HO OH
OH OH
O
Stable carbocation
Tropylium C+
25. C
(2)
H I H I H I
anti aromatic
H=4
resonance
3>2>1
GOC
26. A
Cl
(I) (II) CH2=CH–Cl (III) Et3C–Cl
CH 2=CH Et 3C
(2o) (3)+I group
o
(3 )
Tropylium
Q.Aro.
(IV) PhCH2Cl (V) Ph3C–Cl
Ph–CH2 Ph3C
R.S. more R.S.
(A) I > V > IV > III > II
27. B
O O
– –
6 e 8 e
aromatic anti aromatic
(A) (B)
–
10 e 10 e
–
aromatic aromatic
(C) (D)
so option (B) is aromatic.
28. C
N
(I) (II) (III) ..
O |
N
H
Its Resonating structures are Neutral & Benzene like Resonance
So, maximum aromatic character.
GOC
29. C
– +
(I) CH 3–COOH (II) CH 3COONa
O O
CH 3—C CH3—C
+
O—H O Na
(III) CH3CONH2
O
CH 3—C
NH2
more delocalisation less E.N. of N

O atom is more E.N. due to –ve charge
R.E. order = II > III > I
30. C
O O
(I) (II)
O O
(III) (IV)
more resonance
so max. Resonance energy
31. B
 non-aromatic
 less resonating
as compare to Benzene
6e–
 Aromatic structure
 More no. of resonance structure
 So more stable to non aromatic compound
32. B
(due to hyper conjugation)
GOC
Exercise - 2 Level - 2 | JEE Adv.

1. (a) True
Resonance is a Intramolecular process
(b) False
Resonance involves delocalisation of -electron not -electron
(c) True
Resonance involves delocatization of -electron and lone pair
(d) True
Resonance decreses potential energy of a molecular and increases the stability.
(e) False
Resonance decreases the P.E.
(f) False
Resonance is not only way to increases the stability
(g) True
Resonance is not the only way to increase molecular stability
(h) False
not always
(i) False
Canonical structure not explain all features of a molecular.
(j) True
The resonacne hybrid explains all features of a molecule.
(k) False
Resonating structure are in inaginary but Resonating hybrid are Real.
() True
(m) True
Resonance hybrid is always more stable than all canonical structures.
2. (a) Resonating structure which are equivalent having more resonance energy
(b) The structure which are aromatic they have more energy.
3. (a) If structure has more number. of -bonds then the structure will be more stable.
(b) If the structure which has complete octact of atom which is more stable
(c) Cyclic delocalization of (4n + 2)  electron canonical structure is more stable than acyclic
delocalization of (4n + 2)  electron.
(f) A cononical structrue which as –ve charge is on more electro negative atom is more stable in
compare to –ve charge is on less electronegative atom.
4.
+
:
H2C — N N : H2C = N = N : H 2C = N = N :
(A) (B) (C)
(a) A, B, and C are not constitution isomers they are Resonance form because in this forms the
delocalization of e– are there.
(b) H2C–N N in this structure have a negatively charged carbon is present.
(c) H2C–N N in this structure have a positively charged carbon atom are present.
(d) (A) CH 2–N N (B) H2C=N=N in both the structure N have positively charged.
(e) (B) H2C=N=N (C) H2C–N=N in both the structure N have negatively charged.
(f) Not charged on each structure is zero because they are neutralized each other.
(g) (A) CH 2–N N (B) H2C=N=N
B >A
B because –ve charge on N is more stable in compare to carbon.
(h) (B) H2C=N=N (C) H2C–N=N

in (B) option octet is completed so (B) is more stable.
GOC
5. 6 (i, ii, iii, vi, vii, ix)
(i)
O OH O ONa
+ NaHCO3 + H2O + CO2
O OH O ONa
(ii) HCl + NaHCO3 

 NaCl + H2O + CO2
(iii)
SO3H SO3Na
(vi)
COOH COONa
(vii)
H–C–OH + NaHCO3 H–C–ONa + H2O + CO2
O O
(ix)
CH3–C–OH + NaHCO3 CH3–C–ONa + H2O + CO3
O O
O O
C C
:
O—H H OH
6. (a) H
:
R.S. (1) R.S. (2)

[neutral] [Charged]
R.S. (1) > R.S. (2)
N N
:
(b)
R.S. (1) R.S. (2)
[Complete octet] [incomplete octet]
R.S. (1) > R.S. (2)
CH 2 CH2
(c)
R.S. (1) R.S. (2)
[Aromatic] [Anti Aromatic]
GOC
R.S. (1) > R.S. (2)
CH 2— CH = CH — O CH2= CH — CH = O
(d) R.S. (1) R.S. (2)
[incomplete octate] [complete octate]
R.S. (2) > R.S. (1)
O O
(e)
N N
| |
H H
[O has +ve charge] [N has +ve charge]
R.S.(1) R.S.(2)
R.S. (2) > R.S. (1)
7. (a)
:
CH3 — CH — C N: CH3 — CH = C = N:
R.S. (1) R.S. (2)
Stability order
R.S.(2) > R.S. (1)
R.S. (2) is more stable
So its major contribution in R.H.
CH3 — C = CH — CH — CH 3
R.S. (1)
CH3— C — CH = CH — CH 3
(b) R.S. (2)
O
CH3— C — CH = CH — CH 3
R.S. (3)
Stability order
R.S. (3) > R.S. (2) > R.S. (1)
GOC
(c)
O O O O
CH3 — C — CH — C — CH 3 CH3— C = CH — C — CH 3
R.S. (1) R.S. (2)
O O
CH 3— C — CH = C — CH 3
R.S. (3)
Stability order
R.S. (3) = R.S. (2) > R.S. (1)
 both R.S. (2) & R.S. (3) are eqt. type R.S.
CH3 — CH — CH = CH — N = O
R.S. (1) O
(d)
CH3 — CH = CH — CH — NO 2
R.S. (2)
Stability order
R.S. (2) > R.S. (1)
:
NH2 NH2
:
(e) CH3 — CH2 — C — NH2 CH3 — CH2 — C = NH2

R.S. (2)
R.S. (1)
NH 2
:
CH 3 — CH2 — C — NH2
R.S. (3)
R.S (2) and R.S. (3)

are eqt type R.S. so
Stability order
R.S. (3) = R.S. (2) > R.S. (1)
8. (a) CH3 — C — O — H and CH3 — C — O– Na+

O O
R.S. (1) R.S. (2)
Ionic compound
R.S (2) has higher Resonance
energy because it is ionic compound
and have identical R.S.
COO O
and
(b)
R.S. (1) R.S. (2)

eqt R.S.
So it has higher Resonance energy
GOC
and
(c) Isolated system Fussed system

so it has higher
Resonance energy
(D)
CH2=CH–CH=CH–CH=CH2
aromatic non aromatic

structure structure
more resonance
energy
CH2=CH–O CH2=CH–OH
(a) (b)
in (a) structure O– charge on more E.N. atom and e– density is high so more resonance energy in
a.
O—C—O and H—C—O

9. (a) O O
More Resonance Less Resonance
and CH 2 = CH — CH2
(b) Anti Non -Aro
Aro
(c) and CH2 = CH — CH = CH2

Anti
Aro
(d) and CH2 = CH — CH 2
Aro Non -Aro
OH
10. (a) and
Fries Rule : - More will be the benzoid like structure more will be the Reso. energy
(b) and
2- benzene 1- benzene
GOC
O O
(c) and
Cross Extended
conjugation conjugation
(d) CH2 = CH — OH
less Reso.
and CH2 = CH — CH = CH — OH more Reso.
(e) and
Cross Extended
Conjugation Conjugation
11. (A)
H–N=C=O
H–O–C N
–H –H
N=C=O
O–C N
O=C=N same anion
12. (A)
Br
Quasi aromatic so more ease ionisation.
Cl
2SbCl5
+2
13. (B)
Cl
2SbCl5
H K
14. (B)
H
– +
Bu Li P
Base
abstract the H
GOC
15. (A)
CH3 CH3
(1) (2)
CH3 CH3
PhLi
Strong Base
CH3 CH3
CH2 CH2
Aromatic
Antiaromatic
So phLi reacts readily with 1 But does not add to 2
Br
16. (I)
Bridge headed
carbon +ve charge
unstable
Br
(II)
+ve charge
stablize by
resonance
GOC
Br Quasi
(III) Aromatic
Br
(IV) 3o carbocation
III > II > IV > I

  
Q.A. Reso. 3°
17.
HClO 4
ClO4
|| |
O OH
|
O
18.
AgClO4
Cl ClO4
Ag ClO4
19. Aromatic compounds are
..
N O
..
|
(A) (B) (D)
N
N
6e– 6e– 6e–
H H
KH
20. (A)
+ H
Aromatic 6e-
O O
(B) HBr
Aromatic 6e-
GOC
H H
H I
(C)
Tropylium
(Aromatic)
21. (i) (a) CH 3–CH 2 (b) CH3–CH–CH 3

H=3 H=6
CH 3
(c) CH3–C
CH 3
H=9
carbocation stability –H
(ii) (a) (b) (c)
stability of carbocation –H
(iii) (a) (b) (c)

7 H
(iv) (b) CH—CH—CH

3 3 (c)
H
stability of free radicals –H
(v) (a) (b) (c)
stability of free radical –H
(vi) (a) (b) (c)
GOC
CH3 +I
CH C CH 3 CH CH3 CH 3 C
(vii)
(a) (b) +I CH3
sp
hybridised (c)
+I decrease the stability of carbanion and more E.N. C –sp increase the stabiliyt of carbonion.
(viii) (a) (b) (c)

1º Anion 2º Anion 3º Anion
–I effect
stability of carbonion 
I effect
(ix) (a) (b) (c)

1ºAnion 3ºAnion 2ºAnion
–I effect
stability of carbonion 
I effect
(x) (a) more will be the (b)

angle strain less
will be the stability
(c) (d)
It stable
In chair
on boat form
(xi) (a) (b) CH 2=CH (c) CH3—CH2
more E.N have the -ve charge then It will more stable then less E.N. have -ve charge
(xii) HC C (b) CH 2=CH (c) CH3=CH2
more E.N. have free Radical then It will less stable In compare to free Radical on less E.N.
GOC
22.
CH2 CH2
CH 2
(i) (a) (b) (c)

N
O OMe
O
–M, –I +M, –I
 m,  H,  I
stability of carboncation 
– m, – H, – I
CH2
CH 2 CH2
CH 2
(ii) (b) N (c) (d)

Cl O O CN
–I –M, –I –M, –I
 –NO2 shows more –I effect from –CN

– m, – H, – I
carbonion stability 
 m,  H,  I
CH 2
CH2 CH2
OH
(iii) (a) (b) (c)
OH OH
+M, –I –I
+M
 m,  H,  I
stability of carboncation 
– m, – H, – I
CH2
CH 2
(iv) (a) (b)

Cl
F Cl shows vacant
d-orbital
(v) (a) CH 2=C (b) CH 2 CH3

O +I
resonance
GOC
O O O
H H
(vi) (a) (b) (c)
O O O
crossed R.S. R.S. not show R.S.
CH2 CH—CH
2 2
(vii) (a) (b)

whole compound hyper
Shows Reso. Conjugation
(c) charge is not

distributed It is
delocalized
SP2carbon
(viii) (b)
whole compound
Shows Reso. SP 3carbon
SP2carbon
(c)
SP 2carbon
(ix) (a) whole compound (b) whole compound do

Shows Reso. not shows Res.
(x) (a) hyper- (b)

Conjugation Reso.
(c) (d) charge is not

more distributed
Reso It is localized
GOC
(xi) (b) (c)
CH2
CH 2
CH2 H
C H
H
H C H
H
(xii) (a) H (b) CH (c) Reso
Reso Reso +I
+I H
+hyper hyper
conjugation
CH 2 CH 2 CH2
(xiii) (a) (b) (c) (d)

CH3 CHMe 2 CMe3
23. (a)
(i) CH3–CH–Br (ii) CH3–CH2–Cl
 
Less E.N. more E.N. bond
so more bond strength
(b) (i) CH3–CH=CH–Br
l.p. in R.S. here partical double bond character so bond order increase so bond strength also
increase.
(ii) CH3–CH–CH 3
Br
no l.p. in R.S.
(c) (i) CH 3–C–Cl

O
R.S. are present here so double bond character increases so bond order increase and bond
strength also increase.
(ii) CH3–CH2–Cl
No R.S.
GOC
(d) (i) CH3=CH–CH=CH2

(= – =) R.S. is here so R.S. are present in this compound so double bond character increase so
bond order increase so bond strength increase.
(ii) CH2=CH–CH2–CH3
No resonance.
CH 3
(e) (i) (ii)
CH 2–CH 2 C2H 5
9 H
H increase so
bond strength
increase
24. (a) and CH2 = CH2
(b) CH 3 — C CH and HC CH
(c) CH2 = CH CH = CH2

C
CH2
Single Side Reso.
CH = CH CH2 = CH CH = CH2
C
and
CH2
Single Side Reso. Both Side Reso.
O O
(d) C and C
:
H2N NH2 CH3 NH2
Both Side Reso. Single Side Reso.
O O
(e) C and C
:
Cl Cl CH 3 Cl :
:
GOC
O O
(f) C and C
:
:
:
HN
2
NH 2 H NH2

so more Single more double character
character
25.
:
:
H2N H2N H2N
(i) (ii) (iii)

O atom is more E.N. atom so this compound have double bond character.
26. (C)
NO2
5
1 3
O2N NO2
Br
Br is Bulky So NO2 group goes out of plane So C1 — N & C3 — N Bond are of same length & longer
than C5 — N Bond.
CH3 CH3
or
27. (a)
stability of alkene –H
or
(b)
stability of alkene –H
(c) or
stability of alkene  no. of –H
GOC
28. A + 3H2 Pd / c
 
B D
if reduction of A ring then all ring will be Aromatic
29. (I) (A) (B)

long Reso
(D)
1
HOH
stability of isomeric Alkene
D>C>B>A
(II)
(A)
Reso
(C)
CH3 CH3
(b) <
CH3 CH3
1
HOH
O
(C) >
Reso
1
HOH
CH3 H CH 3
CH3
C=C C=C
(d) H CH 3 < H H
Trans-form cis-form
GOC
1
HOH
CH 3 CH3
(e) CH2=CH CH > CH 2 = C
CH 3 CH 2 — CH3
1
HOH
30. (A) (i) > (ii)
9t has not any 2 bond are in

conjugative system conjugation
(iii) > (iv)
here 3 bond are in Aromatic

conjugation
(B) (i)
It has not any conjugative

system
(ii)
2 bond are in conjugation
(iii)
3-bond are in conjugative

1>2>3
31.
(a) >
not Reso Reso
1
HOH
(b) <
HOH  num of   bond
(C) CH3—CH=CH—CH3 < CH3—CH2—CH=CH2

6n 2H
1
HOH
GOC
CH 2
(d) CH 3 >
1
HOH
32.
HOC  number of Carbon in hydrocarbon
1
HOC 
Stability of isomeric Alkene
(a) CH3 — CH2 — CH2 — CH2 — CH2 — CH = CH2

2H
(b) CH3 —CH — CH 2 — C = CH2

CH3 CH 3
(c) CH 3 —C = CH — CH — CH3
CH3 CH3
CH3
(d) CH 3 —C — HC = CH — CH3
CH3
CH3 CH3
(e) CH3—C — C = C — CH3

CH3 H
8-Carbon
33. (i) (a) < (b)

Reso
Not Shows Reso.
(ii) (a) > (b)

repulsion
(c) less > (d)

repulsion
(iii) (a) > (b)
GOC
(c) > (d) >
(e)
(iv) (a) > (b) >
(c) because of more [b>c>a]

Reso. Its losses
the energy
(v) (a) > (b) >
(c)
(vi) (a) > (b) >
(c) (HOH per benzeue

ring)
more Reso
more Energy loss
e HoH
loss
(vii) (a)
Resonance

(b)
hyper conjugation
(viii) (a) (b)

Reso. hyper conjugation
1
HOH
stability of isormeric Alkenes
GOC
34. (i) (a) (b) (c)

6-carbon 7-carbon
8-carbon
HOC  num of Carbon in Hydrocarbon

c>b>a
(ii) (a) (b) (c) (d)

a>b>c>d
more repulsion
(iii) (a) (b) less
repulsion
1
HOC
stability of isormeric Alkenes
b>a
(iv) (a) (b) (c)

3-Carbon 4-carbon 5-carbon
c>b>a
a
H—CH2
d
H—CH—CH—C—CH3
c b
He H H
35.
CH2
f H
1
C–H Bond Energy 
stability of Carbon free Re dical
Stability order of
Carbon free Radical .. d>f>b>c>a>e
There fore C — H Bond energy .. d<f<b<c<a<e
36. Anthracene is 14  e– s system
i.e. there are 7 bonds
Expected (theoritical) heat of hydrogenation
= – 28.6 * 7 = –200.2 Kcal/mol
Observed (experimental)
heat of hydrogenation = – 116.2
R.E = obseved value – Expected value
= – 116.2 – (–200.2)
= 84 Kcal/mol
GOC
37. (I) C6H5 – OH (II) F OH

+M > –I
(III) Cl OH (iv) O2N OH

–I > M –M
IV > III > II > I
38. (A) (b)
(c) (d) CH2 – CH – CH3
The conjugate base of compound (b) is
most stable due to aromaticity (i.e. )

–
CH3
OH H3C OH
39. (A) (B)
CH 3
O2N
NO2 –I CH3
–I
CH3
H3C OH OH
(C) (D)
H3C NO2 H3C
–M NO2
–I
Maximum acidity (C). Ans. (C)
COOH
COOH
40. (A) (B)
OH
+M
(most acidic)
COOH COOH
OH
(C) (D) (ortho effect)
OH
+I
Compound (B) is less acidic due to (+M) effect of –OH group because it is present on pera
position.
GOC
41.
OH OH
OH
(I) (II)
O O
O O
–
– –  O
O O
–O   –
–
O 
O–
O
4 eq. Aromatic R.S.
HO OH
(III)
O O
– –
O O

–  –
O O
Non aromatic
1
acidity  Pk
a
acidity (ka) order = I > II > III

Pka order = III > II > I
42. (1) Phenol (2) Ethyl alcohol
OH
C2H5OH
(3) Formic acid (4) Benzoic acid
COOH
H – C – OH
O
1 1
pH  
acidity stability of conjugate Base
Stability of conjugate base
= C2H5O– > C6H5O– > C6H5COO– > HCOO–
43. Compound which are stronger acid than H2CO3 gives CO2 with NaHCO3.
 Compound (A), (B), (C), (D) all are stronger acid than H2CO3.
GOC
44. (A)
(R) Aromatic Compound
(B)
(S) Anti Aromatic Compound
:NH
(C)
(R) Aromatic Compound
:
N
H
H
N
:
(D) (R) Aromatic Compound
(P) Hybrid state of each atom sp2

45. (A)
(T) Obeys huckel's Rule
(P) Hybrid state of each atom is sp2

(B)
(S) Non - Aromatic
sp3 carbon
(C) (S) Non - Aromatic
2
(P) Hybrid state of each atom sp
(D) (Q) Anti Aromatic
(P) Non - Aromatic

:
46. (A) NH
(R) Resonance
(P) Non - Aromatic

(B)
(R) Resonance
(P) Resonace
(C)
: :
O (R) Aromatic
(P) Non - Aromatic

(D)
(R) Resonance
GOC
: :
:
47. (A) CH3 — O — CH2 or CH3 — NH — CH2
O atom is more E.N. atom form N -atom so O-atom can not denote the l.P easily from N-atom in
Resonance so
(R) Not Resonating structure of each other
(S) Resonance is present in both carbocation
:
(B) CH 3 — O — CH2 — CH2 or CH3 — O — CH2
:
(C) or
Reso. (SIR effect)

CH2CH3 CH—CH3
(D) or
Reso.
(R) Not resonating structure of each other.
GOC
Exercise - 3 Subjective Question
1.
(i) (a) H – F (b) H – Cl
– Cl–
F
(c) H – Br (d) H – I
Br - I–
In group we see the size factor more the size, more stable the anion, more the acidity.
d > c > b > a (acidic strength)
CH4 NH3
–H + –H+
(ii) (a) – (b)
CH3 NH2
H2O H–F
–H+ –H +
(c) (d)
OH– F–
In period we see the E.N. factor more the electron negativity, more stable the anion, more the
acidity.
– – – –
E.N. order  F > OH > NH2 > CH3
Acidity order = d > c > b > a
(iii) (a) CH3 – CH2 – O – H
–
+I CH3 – CH2 – O
More stable
(b) CH 3 – CH – O – H
CH3
CH 3 – CH – O–
CH3
2(+I) effect
CH3
(c) CH 3 – C – O – H
CH3
CH3
CH3 – C – O–
CH3
Three + I group less stable
(acidic strength) a>b>c
(iv) (a) F – CH2 – CH2 – O – H

 F – CH2 – CH2 – O–
(b) NO2 – CH2 – CH2 – O – H
 NO2 – CH2 – CH2 – O–
(c) Br – CH2 – CH2 – O – H
GOC
 Br – CH2 – CH2 – O–

(d) N H3 – CH2 – CH2 – O – H

 N H3 – CH2 – CH2 – O–

–I order = – N H3 > –NO2 > – F > –Br
acidic strength = d > b > a > c
2. (i) (a) CH3 – COOH –H+ CH3 = C – O–

||
O
–H+ –
(b) CH3 – CH2 – OH +I CH3 – CH2 – O
–
O
(c) C6H5OH –H+ C6H5 – O–

(Phenoxide ion)
O –
O O
S
(d) C6H5SO3H
[–I order – C – R > Ph]
O
(More the resonating structures,
more the stability)
d>a>c>b
COOH COOH
(ii) (a) (b)
–H+ –H+
– –
C –O C–O
3 O 2 O
sp sp
COOH
(c)
–H+
–
C–O
O
sp
(more-I)
Stability = C > b > a

acidity = c > b > a
COOH
COOH
–H+
(iii) (a) –
COO
COO–
GOC
COOH
CH2
COOH
–H+
–
(b) COO
CH2
COO–
CH2 – COOH
CH2 – COOH
–H+
–
CH2 – C – O
(c)
O
–
CH2 – C – O
O
[a > b > c]
O
3. (a) Cl – CH2 – C – O – H
O
–H+ Cl – CH 2 – C – O - (one -I group)
O
(b) Cl – CH2 – C – O – H
Cl
O
–H+ –
Cl – CH2 – C – O (two -I grop)
Cl
Cl O
(c) Cl – C – C – O – H
Cl
Cl O
–
–H+ Cl – C – C – O (Three –I groups)
Cl
(most stable)
Ans. c>b>a
O
(ii) (a) CH 3 – CH 2 – CH – C – O – H
F
O
–H+ CH3 – CH2 – CH – C – O –
F
(b) CH 3 – CH – CH2 – C – O – H
F O
GOC
–H+ CH3 – CH – CH2 – C – O –
F O
O
(c) CH2 – CH2 – CH2 – C – O – H –H+
F
In this type of case are see
CH2 – CH2 – CH2 – C – O –

F O
"DNP" rule.
Distance Power
Number
Acidic strength = a > b > c
O
(iii) (a) NO2 – CH2 – C – O – H
O
–H+ NO2 – CH2 – C – O–
O
O
(b) F – CH2 – C – O – H
O
–H+ O–
F – CH2 – C – O
O
(c) Ph – CH 2 – C – O – H
O
 –H+ –
Ph – CH2 – C – O
O
O
(d) CH 3 – CH 2 – C – OH
O
–H+ CH3 – CH 2 – C – O–
Acidic Strength : a > b > c > d
4.
:
:
:
(i)(a) :OH (b) :OH (c) :OH
NO2 Cl CH 3
(strongel acid)
  
– – –
O O O
NO2 Cl CH 3
–I –I +I
(most stable
GOC
conjugate base)
Acidic strength = a > b > c
:
:OH
:
:
:O – H :O
(ii) (a) Cl (b) (c)

Cl
Cl
Inductive effect by distance decreases.
Acidity order a > b > c
:
:
:OH :O – H
(iii) (a) (b)
–H+ –H+
– –
O O
CH 3
:
:O – H
:
:O – H
(c) (d)
–H+ –H+
–
O
–
O
CH 3
stability of Conjugate base : d > b > c > a

acidity order : d > b > c > a
:
:OH
O
N
5. (i) (a) O
(–M) Hydrogen Bonding

:
:O – H
:
:O – H
:
:O – H
(b) O (–I) (c) N (d)

N O
O O
(–M)
Acidity order = c > a > b > d
GOC
:
:O – H :O – H
O
N
O
(ii) (a) (b)
NO2 H–Bonding
–M (–M)
:
:
:O – H :OH
NO2 O2N NO2
(c) (d)
NO2 NO2
–I –I
Acidity order = d > c > a > b
O
O
C–O–H
C–O–H
CH3
–H+
O –H+
6. (i) (a) –
(b) O
C–O –
C–O
CH 3
Due to ortho effect

COOH goes out of plane
b > a So max. acidity
COOH
Cl
(ii) (a)
COOH
Br
(b) Br is more bulky then Cl ortho effect b > a
O
.. O
C–O
.. – H ..
C–O
.. – H
..
:O
.. Me O
.. Me
O O
(iii) (a) – (b) C–O
–
C–O
O Me
O Me +I
(+M)
GOC
O
C–O–H
..
O
.. Me
O
(c) C–O
–
O Me
Ortho effect max. acidity
Acidity order c > b > a
O O
C–O–H C–O–H
(iv) (a) (b)

NO2
N –I
O O
–M
–I
O
C – OH
NO2
(c)
Ortho effect
Acidity order = c > a > b

OH OH
7. (i) (a) (b)
CH3 NO2
–M
–I
OH OH
(c) (d)
Cl NH2
Strongest acid  (b)
OH OH
(ii) (a) (b)

NO2 F
–I is more
GOC
OH OH
(c) (d)
CH 3
So maximum acidity of a.
OH OH
O Me
(iii)(a) (b)
+M O Me
–I
OH OH
(c) (d)
O Me
–M
acidity  with drawing tendency of group.
so (b) max. acidity.
8. (i) Cysteine :
COOH
HS
NH2
1
Acidity  Pk
a
Acidity order = –COO – > –S – > –NH –

10.8 8.3 1.8
(ii) glutomic acid :
HOOC COOH
1
2
NH2
acidity : – COOH > – NH2

acidity of –COOH (2) > – COOH (1)
..
due to – I effect to –NH2
order of acidity :– COOH (2)> –COOH (1) > –NH2
order of Pka : – NH2 > – COOH (1) > – COOH (2)
OH OH
9. (a) , ,
COOH
cyclohexane carboxilic acid
GOC
acidity stablity of CB
COOH OH OH
acidity = > >
Pka order = 3 < 2 < 1
(b) 1 - butyne, 1-butene,

4 3 2 1 CH3  CH2  CH  CH2
CH3  CH2  C CH
2
sp sp
acidity order = 1 > 2 > 3
Pka order = 1 < 2 < 3
butane
CH3  CH2  CH2 – CH3
3
sp
(c) Prophanoic acid, 3-Bromo propanoic acid

3 3 1
C  C  C  OH
C  C  C  OH
O Br O
–I
acidity 3 > 2 > 1 3<2 <1
2-nitro propanoic acid
2 1
C  C  C  OH
NO2
(–I)
(d) Phenol, O-nitrophenol,
OH OH
NO2
–M
–I

PKa order = 2 < 1 < 3
O-cresol
OH
CH3
+I
+H
GOC
(e) Hexylamine, aniline, Methyl amine
NH 2 (3)
–
CH3  NH2  CH3  NH
–
–H NH
(2)
(1) CH3  CH2  CH2  CH2  CH2  NH2 –H
–
CH3  CH2  CH2  CH2  CH2  CH2  NH
acidity  stability of conjugate Base
stability order = 2 > 3 > 1
Pka = 2 < 3 < 1
10. (a) (1) CH3 – CH2 – Br
CH 3 – CH – Br
(a) (2) CH3 – NO2
CH2 – NO2
–
(2) CH2  NO2
–I
O –
–
(1) (1) CH 2–C–H
CH2  C  CH3
||
O
–
(2) is stronger acid (2) CH 3–C–CH–CN
|| –I
O
(2) > (1) (2) > (1)
–
(2) CH –NO
2 2
(2) > (1)
GOC
OH
OH
11. (a) as (2)

O = C – CH3
–M
acidity  – M effect
So (2) is weaked acid
OH
OH
(b) as (2)
O = C – CH3
CH3
–M +H
So (2) is weaker acid
– –
SH OH S O
(c) or
Acidity  stability of C.B.

– –
S O
Stability of C.B. = .>
–
O
So is weaker acid
COOH
12. (a) –
COO
GOC
O O
COOH or
|| O
+ ||
N – C – OH
O
–
–
O2N COO
–M
acidity  – M effect
so (2) is more acidic
(b) CH3  CH2  CH2  OH orCH3 – CH = CH – OH
| 
CH3 – CH2 – CH2 – O – CH3 – CH = CH – O–
Showing Resonance so
more acidic
So (2) is stronger acid
(c) CH3–CH = CH–CH2 –OH or CH3–CH= CH – OH

CH3 – CH = CH – CH2 – O – (2) CH3–CH=CH – O–
Show Resonance
so more acidic
so (2) is stronger acid
1
13 (i) Basicity 
Stability of anion
Stability order F¯ < Cl¯ < Br¯ < I¯ (size)
Basicity order F¯ > Cl¯ > Br¯ > I¯
(ii) Stability order CH3  NH2  OH  F  (E.N.)
Basicity order CH3  NH2  OH  F 
.. ..
(iii) R – NH2 Pn – NH 2
.p. localised .p. delocalised
(more basic) (weak base)
..
R – C – NH2
O
.p. more delocalised
(least base)
basicity order a > b > c

(iv) In gas phase basicity  (+I) effect.
Basicity order
NH3 < Me NH3 < Me NH Me < Me N Me
+I +I +I +I +I
Me
+I
(v) In H2O, 3°-amine is less basic than 1°-amine due to less solvation.
Basicity order : 2°–amine > 1°–amine > 3°–amine > NH3
GOC
14.
O
(i) .. ..
NH NH N
Me
.p. localised
.. .p. delocalised
NH2 ..
NH2
NH
..
(ii)
.p. localised
(2° amine)
1°–amine
Basicity c > a > b

.. .. ..
N N N
(iii)
O2N Me F
Strong-I +I-effect Weak –I effect
1
Basicity 
(I) effect
 (+I) effect
Basicity
.. b > c >a
..
NH2 NH2
+
(iv) (a) NH3 (b) Cl
Strong-I-effect
+
of Weak –I effect of
–NH3, least basic –Cl, less basic
.. ..
NH2 NH2
(c) CH3 (d) No effect of any group.

+I effect of –CH 3, Weaker than C, but stronger
most basic than a & b compound.
.. ..
15. (i) (a) CH3 CH2 NH2 (b) CH3 – CH = NH
sp3 sp2
Least electronegative
most basic
order a > b > c
..
(c) CH3 – C  N
sp
most electronegative
least basic.
GOC
..
(ii) (a) CH3 – C – NH2
O
least basic, l.p. of
nitrogen is delocalised.
..
CH3CH2 NH2
(b)
Lone pair localised
..
CH 3 – C – NH 2
NH
..
(c) More basic due to
delocalisation of only
one l.p.
.. ..
(d) NH 2 – C – NH 2
NH
Most basic, due to more
delocalisation of l.p.
Basicity order d > c > b > a
(iii) (a) (b) (c)

NH
.. N
..
NH
.. 2
* Compound 'a' is least basic, because l.p. of Nitrogen will more take participate in
resonance due to aromaticity.
* Compound 'b' is most basic, because its l.p. is localised.
* Compound 'c' is more basic than 'b' because its l.p. is delocalised.
b > c > a.
O
..
NH – C – CH 3
(iv)
l.p. of nitrogen is in conjugation with benzene as well as – C – CH 3 , least basic.

O
..
NH2
l.p. of nitrogen is in conjugation only with benzene. it is more basic than compound 'a'.
..
NH – CH 2CH3
due to extra +I effect of –CH2CH3 group, compound 'c' is most basic than a & b.
order c > b > a
GOC
NH2 NH2
CH3 CH 3
(v) b>a
Me Me
No2 NO2
Compound a is least basic than b, due to ortho effect of two –CH3 group.
NH2 NH2
16 (i)
NO2 CN
–M –M
NH2 NH2
OMe NH2
+M +M
Order of –M –NO2 > –CN
Order of +M –NH2 > –OMe
1
Basicity  +M 
M
 Basicity order d > c > b > a increasing order.
NH2 Ortho effect NH2 NH2

CH3
(ii)
CH3
+I
CH3 +H
Compound C is most basic due to +H effect of –CH3 group. But compound a is least basic due to
ortho effect of –CH3 group.
Basicity order c > b > a
NH2 NH2
NH2 Ortho effect
NO2
(iii)(a) (b) (c)
NO2
+I
NO2
–M
Basicity order b > a > c.
NH2 NH2 NH2 Me

CH3 C – Me
(iv) Me
Ortho effect, Greater ortho effect,
less basic least basic.
Order a > b > c
GOC
Me Me
N Me Me
N
(v)
OMe
+M OMe –I
Me Me
N
SIR
OMe
Basicity order c > a > b
17. (i) (a) (b) ..

.. N
N2
sp H
2
sp & delocalisation of l.p.
S
(c) (d) d is strongest base
N N
2 3
H sp H sp
In compound 'd', hybridisation of N is sp3. i.e. less electronegative and –I effect of S is less.
(ii)[b] In compound b, N atom is sp3 hybridised, and l.p. of nitrogen is localised.
(iii) Compound a is most basic because charge density on double bonded nitrogen is very high due to
resonance.
(iv) In compound a, the e– charge density is very high due to –ve charge.
1
18. (i) Basicity 
E.N. of anion
Order of E.N.
CH3CH2 < CH2 = CH– < HC  C– < CH3CH2O–
(b) (a) (d) (c)
Decreasing order of basicity b > a > d > c.

..
NH 2
(ii) (a) l.p. is in conjugation
only with benzene ring.
..
CH 2 – NH2
(b)
l.p. localised, most basic
(c) NH2
NO2
Ortho effect
GOC
..
C – NH2
(d) O
l.p. is in conjugation with
–C– group. Which is most
O
with drawing.
Decreasing order of basicity:b > a > c > d

O CH3 CH3
Nb
H2N – C – H2C CH2– NH – C – CH 3
c
NH
19. a
N
CH3 d CH3
a is most basic due to high charge density.
b is more basic than d and c due to ortho effect.
c is least basic because l.p. of nitrogen is conjugated with – C – group..
O
Order : a > b > d > c
NH2 NH2 NH2

NO2
20.
NO2
I II
least basic due –I NO2
–M
to ortho effect III
II > III > I
NH2 NH2
21. (I) (II)
NO2
–M
NH2 NH2
(III) (IV)
OCH3 CH3
+M +H
Order : III > IV > I > II
..
22. N
H
This lone pair very much delocalised because of getting Aromaticity so do not donate lone pair so
it is least basic.
GOC
23. (a)(I) CH3NH2 or (II) CF3NH2
F
.. ..
CH3 – NH2 F C – NH2
+I F –I
have more tendensity
to donate the pair of e–.
NH
(b) CH3CONH2 or
H2N NH2
In aquous solution 2° are more basic because of solvation energy.
2>1
(c) n-Pr NH2 or CH3CN
..
CH3 – CH2 – CH2 – NH2
3
sp 'N'
1>2
..
CH3 – C  N
sp Nitrogen
more E.N weak basic
(d) C6H5N (CH3)2 or 2,6-di methyl-N, N-dimethyl aniline.
H3C Goes out of plane

H3C CH 3 .. CH 3
N So more basic
N
H 3C CH3
Ortho effect
So 2 > 1
(e) m-Nitro aniline or p-nitro aniline

.. ..
NH2 NH2
NO2
–I NO2
–M
So more basic 1>2
24.
(a) p-methoxy aniline or p-cyano aniline
NH 2
NH2
OCH3
+M CN
So more basic 1 > 2 –M
GOC
(b)
Pyridine or Pyrrole
..
N
.. N Delocalised lone pair
Localised lone pair H so least basic.
1>2
..
(c) CH3C  N or CH3CH2 NH2
 
sp nitrogen so less basic sp3 Nitrogen 2>1
.. ..
NH2 NH2
25. (a) or
NO2
–M so more tendency to
donate the pair of e– of NH2
in the ring. So weak base
–
(b) CH2=CH–CH = CH– CH2 or CH2 = CH – CH2–
long resonance
So–ve charge delocalised
So weak base
O O O O
(c) –

O – C – C – OH or HO – C – C – OH
Anions are more Basic than Neutral.
So (2) is a weak base.
.. ..
OH OH
CH 3 CF3
+I –I
or
Strong Base Weak Base
.. .. .. ..
NH2 NH2 NH2 NH 2
CH3 NO2
26. (a) (i) (ii) (iii) –M (iv)
Ortho effect Localised l.p. of N

3<2<1<4
NH2 NH2 ..
NH2 CH2 – NH2
CH3
(b) (i) (ii) (iii) (iv)
CH 3
Ortho effect +I CH3
+H
1<2<3<4
–
27. –
(a) (i) OH (ii) CH3COO –
(iii) Cl
–
– >
Stability – Cl –
CH3COO > OH
– – –
Basicity order : OH > CH3COO > Cl
1 2 3
GOC
(b) (i) CH  C– (ii) CH2 = CH– (iii) CH3CH2–
Stability = (i) > (ii) > (iii)
Basicity = (i) < (ii) < (iii)
2
sp ..
(c) (i) CH 2 = CH – CH2 – NH 2
3
sp ..
(ii) CH 3 – CH2 – CH2 – NH 2
..
(iii) CH  C – CH2 – NH 2
sp
Basic strength : 3 < 1 < 2
..
NH – C6H5
NH2 NH2
28. (a) (i) (ii) (iii)

More resonance
More delocalised
so least basic
(ii) < (i) < (iii)
NH 2 NH 2 NH 2
Cl
(b) (i) (ii) (iii)
Cl
Ortho effect More –I Cl
Less –I
1 <2<3
NH2 NH2 NH2

(c) (ii) (iii)
H3C O2N
+I +M
2>1>3
29. (a) CH3NH2 (Neutral), CH3+NH3 (+ve charged), CH3NH– (–ve charged)
2<1<3
(b) CH3O–, CH3NH–, CH3CH2–
More E.N. more stable 1 < 2 < 3
– – –
(c) CH3CH = CH , CH3CH 2CH 2 , CH 3 – C  C
2 3
sp sp sp
Stability = 3 > 1 > 2
Basicity order = 3 < 1 < 2
GOC
.. H
NH2 NH2 N
30. (a) 2>1>3
More resonance
least basic
H
N
..
N–H N:
(b) 1>2>3
Localised l.p.
l.p. Delocalised
..
H–N N N–H N–H
(c)
Participate in
resonance so
least basic
6
5 7 +
5 N 5 –
4 6
4
N1 1 N N–H
8 3
31. N N N :N – H N 2
2 –
1 3 1 3
9 4
N 6e
2 2 H 3 aromatic
Pyrimidine Purine
Imidazole
Localised lone pair
– Protonation takes Three basic 'N'
of N, 6e ,aromatic
place on N–1 N1, N3, N7
So (A), (C) & (D) are aromatic.
GOC
Exercise - 4 Previous Year| JEE Main

1. B
In p-nitroaniline, acetonilide and aniline, the l.p. of N is in conjugation with aromatic system so
it is delocalized and is not freely available for donation so other option is less basic as compare to
benzyl amine because they have l.p. on N which are not in conjugation with benzene ring so it is
free for donation to an electrophile.
2. C
CaC2 is represented as [:CC:]–2 Ca+2. It has one sigma bond and two pi bond.
3. D
Thus due to the presence of an unpaired electron, free radical are chemically active.
CH3 + CH3 CH 3 + CH 3
4. C
Lowest Pka  highest Pka  high acidity
As R increase acidity decrease in carboxylic acid due to increase in e– density on O–H bond where
R is length of alkyl chain.
So HCOOH is more acidic and least value of Pka.
5. D
More is the resonance or -H, more will be the stability of free radical.
(CH3)2 C H < (CH3)3 C < (C6H5)2 C H < C6H5 C
6. B
e— withdrawing groups increase the acidity and e— donating groups decrease the acidity.
7. C
Due to less steric effect and more +I effect and effective solvation.
8. D
Nitro group decreases the e— density at benzene ring.
9. B
e— withdrawing groups stabilise and e— donating groups destabilise the carbanions.
10. D
Correct order of increasing basic strength is
RCOO— HC C— N—H R—
11. A
OH OH OH OH
NO2
CH3 –I NO2
+H, +I –m, –I
– m, – H, – I
acidic strength 
 m,  H,  I
GOC
12. D
S
6 e– 10 e
–
6 e–
aromatic aromatic aromatic
4 e– but not in conjugation

so non-aromatic
13. B
CH2
> CH2=CH–CH2 > CH3–CH2–CH2
resonance H = 2 1º alkyl
benzylic carbon
more resonance
14. D 15. C 16. A 17. B 18. B 19. D 20. C
21. A 22. C 23. C 24. B 25. C 26. B 27. A
28. D 29. D 30. A 31. C

32. B
Sol.
sp3 carbon at om (Not planer)
Hence It is non-aromatic.
33. A
1
Sol. Acidity of carboxylic acid -R>-H>-I 
R   H  I
COOH COOH COOH OH
NO2 CH3
(-M) (+H)
II III IV I
GOC
34. D
35. A
a  sp3 b  sp2 c  sp2
36. D
6  electron
6  electron
37. B
OH
O
C
 CH2
 CH 3
CH 3 CH 3
–3
10 %
H
O O O O

 C
CH 3 CH 2 CH 3 C
CH3 CH CH 3
76%
stable due to intr amolecular

H-bonding
38. A
It contain 12 five membered ring & 20 six membered ring
39. D
NaH is used as reducing agent.
The p on nitrogen in pyridine makes it basic
40. A
O O
CH3 – C – N – C- CH3
H
Due to higher resonance, p of N is not available for accept H+
So it is least basic.
41. A
: 6 electron
GOC
Exercise - 4 Previous Year| JEE Main + Adv.

1. C
l.p – l. p repulsion
: :
H2C = CH — CH — CH — O — CH3
.. SiMe3
|
N N
2.
Me Me SiMe3 SiMe3
Me
Pyramidical Trigonal planar
Given compounds are not isostructural delocalised of l.p. of nitrogen in vacant d-orbital of silicon
makes compound planar.
3. D
SO3H SO3Na
NaHCO3
+ H2CO 3 H2O + CO2
–+
OH ONa
NaHCO3
+ H2CO 3 H2O + CO2
NO2
4. C
OH
OH OH OH
OH
(i) (ii) (iii) (iv)
OH
OH
Effective H-bond bonding

B.P  intermolecular H-bonding which is iii > ii > i > iv
 molecular mass
5. A
Repulsion
O
N
O
6. D
COOH
OH
GOC
B.P.  inter molecular H-bonding
hydrogen bonding
COOH
OH
Intra molecular H-bonding
7. B
In hyperconjugation –p orbital overlap and conjugation are possible.
8. D
ct
fe
ef
+I
: :
(i) +I O O
ct
:
fe
ef
(ii)
2º carbocation
: :
(iii) O O
+I effect
:
(iv)
1º carbocation
I > III > II > IV
9. A
OH OH COOH COOH
(i) (ii) (iii) (iv)
Cl CH3
eqt.R.S. eqt.R.S.
– –
O O COO COO
Cl CH3
–I +H
Ph - COO– is more stable than PhO— III> IV>II> I
GOC
10. B
incomplete octact
(i) H2C = N = N (ii)

H2C — N = N
H2C — N = N
(iii) (iv) H 2C — N = N
P-orbital
-ve on less E.N. atom
Resonance
I > III > II > IV
11. D
H H H H
1 2 3 4 5
H3C — C — C — C — CH3 H3C — C — C — C — CH3
:OH H CH3 :OH H CH3
:
P-orbital Reso.
12. 2
:
O:
NH3 — CH2 — CH2 — CH2 — CH2 — CH — C
: :
O:
NH2
:
:
because —NH2 and –COO– both have lone pair (two basic qp in following compound).
13. All carboxylic acid and phenol are soluble in aqueous NaOH. four compouds are soluble in aqueous
NaOH and 3° amine
14. C
OH COOH COOH COOH

OH
(A) (B) (C) (D)
NO2 OH CH3
O– COO COO– COO

OH
NO2 OH Intramolecular
CH3
–I H-Bonding
–M, –I
15. 6
CH 3 CH2—CH 3
This compound have 6 H So It form six hyperconjugative structure.
GOC
16. B
CH 2 = C = CH 2
2
sp
2
sp sp
17. B is antiaromatic
18. D
Benzoic acid and benzene sulphonic acid are stranger acid so liberate CO2.
Pka of PhOH (carbolic acid) is 9.98 and that of carbonic acid (H2CO3) is 6.63 thus phenol does not
give effectvesence with HCO–3 ion.
19. A
vacant
p-orbital
H
CH3
C C H
CH3
H
It is p(empty) electron delocalisation.
H
H C
H
H
C C
H CH 3
It is electron delocalisation.
20. 9
O O
(1) (2)
O O
(3) (4)
O O
(5) (6)
O O
(7) (3)
O O
(8) (9)
GOC
21. A
– – – –
O O O O
CO2H H H CO2H H
C C
HO OH O O OH O
+ +
(I) –H (II) –H
CO2H
CO2H
1
(III) (–I) (IV) Acidity
y  (–I)
I) 
(M)
OH OH
22. 5
Are Aromatic
NH2 NH
> > > N
NH2 NH NH2 NH2 N NH NH
23.
(IV) (I) (II) (III)
order of basicity is
24. Acidic strength  stability of conjugate base

acid conjugate base
O
(1) H–C C–C–OH H–C C–C–O
O O
H
(2) C=C CH 2=C–C–O
H OH
H O
O
O
(3) MeO MeO C–O
OH
OH O
(4)
O O
–I effect increase the stability anionic base where +m & +I decrease.

1 > 2 > 3 > 4.

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GOCSHEET2021

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CONTENT

• Cleavage takes place due to

HETROLYTIC BOND FISSION

INTERMEDIATES OF ORGANIC COMPOUNDS

ELECTRONIC DISPLACEMENT EFFECT

(1) Permanent effect :

if X i.e more electronegative

* O– < O < O+ (–I effect order)

Eg. CH2 = CH (–I of –ph)

Order of –I effect showing group:

(–I order) – C  CH > – CH = CH2

– CH2 > – NH > – O > – CMe3 > – CHMe2

Bond Strength : CT3 > CD3 > CH3 (+ I of T > D > H)

APPLICATION OF INDUCTIVE EFFECT

MESOMERIC EFFECT (RESONANCE EFFECT)

* Consider another conjugated system

MESOMERIC EFFECT IN PHENOL (+ M EFFECT)

If the movement of e– is towards ring  (+M effect)

(a) (b) (c)

N=O N=O N=O N–O

* Above compound have +M of –OH and –M of NO2 group.

(resonating structures) (Resonance hybrid)

CONDITION FOR SHOWING RESONANCE

(A) (B) *(C) *(D)

Because all carbon atoms are sp2 hybridised.

(2) -bond alternate to + charge

Eg. CH2 = CH – CH2

CH2 – CH = CH2 CH2 CH CH2

Eg. CH2 = CH – CH2

(4) CH2 = CH – NH2 CH2 – CH = NH2

1. Resonance takes place due to delocalization of e–.

(c) Resonance (d) Resonance

4. In Resonance No. of unpaired e– remains the same

CH2 = CH – CH= CH – NH2

(4) Compound with more covalent bond will contribute more

Cross conjugation < Extended conjugation

Q.2 (a) CH2 = N = N

(c) CH2 – N = N (incomplete)

Q.4 (a) CH2 = CH – F

(CH3)3C > (CH3)2CH > CH3 – CH2 > CH3

Properties of Free Radical

(unpaired electron stay perpendicular to the plane)

ALLYLIC FREE RADICAL

CH2 = CH – CH2 CH2 – CH = CH2

CH2 – CH = CH2 > (CH3)3C

BENZYLIC FREE RADICAL

CH2 CH2 CH2

(di-benzylic free Radical)

(Tri-benzylic free Radical) No. of Resonating structure = 10

Compare the stability of the following free Radicals

(Therefore this resonating structure is not possible)

(3°) (2°) (1°) methyl free radical

* Bond length  stability of free Radical

CH3 – CH2 – –CH2 – CH = CH – CH2 – –CH3

CH3 CH2 – CH3

while drawing the resonating structure of the

CH2 CH2 CH2

CH3 CH3 H–C–H

(a) (b) (d)

1° allylic 2° allylic + 2H

allylic carbocation Actual Resonance

CH2 – F.. CH2 F CH2 = F

(a) (b) (c) (d)

(a) (b) (c)

(A) (B) (C) (D)