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GOC
EXERCISE 1 HINTS & SOLUTIONS
1. A
Bond Formation is-
(A) Always exothermic
In Bond formation heat always release.
2. C
CH2=CHCN CH2=CHC N
3 2 1
sp2 sp
(C) sp2 sp overlap
3. A
4. C
5. B
Complete Resonance
6. A
7. B
8. A
3 2
sp sp sp (more E.N.)
(less E.N.)
10. D
11. A
12. C
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GOC 2
13. C
I 2 1
(a) FCH2CH2COOH F CH2CH2COO
I 2 1
(b) ClCHCH2COOH Cl CHCH2COO
| |
Cl Cl
I
1
(c) FCH2COOH F CH2COO less distance
more acidic
2 1
(d) BrCH2CH2COOH Br CH2CH2COO
I
1
acidity Ka Pkb
PKa
acidity order = c > b > a > d
Pkb order = c > b > a > d
14. B
+I
(A) CH3COOH CH3CO
||
O
+I
..
(B) MeO CH2 COOH MeO .. CH2COO
F
|
(C) CF3COOH FCCOO
|
F I
Me Me
(D) COOH COO
Me Me
Acid strength +I
order :- d<a<b<c
15. A
16. C
17. C
..
CH 3NCH 3
(A) Tri methyl amine |
CH3
NH2
(B) aniline =
..
(C) Di methyl amine = CH 3NH CH3
More electron density on 'N' more Basicity (it is more basic than 3 amine because 3
amine is sterically hindered)
(D) Methyl Amine = CH3NH2
(C)
19. D
(I) CH2 = CH CH = CH2 I, II, III are canonical structures to each other.
(II) CH2CH=CHCH2
(III) CH2CH=CHCH2
All
20. C
I II III
O O O
|| | |
C C C
H OH H OH H OH
Neutral 3 covalent 4 covalent
structure Bond Bond
(C) I > III > II
21. D
IV str. is least stable CH 2=CHCHCHOCH 3 due to repulsion b/w & l.p..
22. C
OH
23. D
ON N=O
24. A
N N N N N
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GOC 4
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
27. C
28. B
m O
p OH
m O
ve charge comes at ortho & pera position so e- density is maximum on ortho & pera
position.
29. C
30. D
NO2
NO2
NO2 (I effect) occur at two places
So e density is minimum.
EXERCISE-2 LEVEL I
1. A
. . . .
C6H5CH C6H5 C6H 5CHCH=CH 2 CH3CH CH3 C6H 5CH CH3
(I) (II) (III) (IV)
more R.S. Reso. + hyper conj. (2) + I group R.S.
. .
(V) CH3CHCHCH2CH 2 (VI) CH3CH2CCH3
|
CH3
(1) + I group (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
order
(A) III > II > I > IV
3. C
4. B
CH3
C CH3
CMe3
CH3 CH 3
CH3 CH3
(I) No alpha hydrogen (II)
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GOC 6
CH3
+
C CH 3 CHC3
CH3
CH 3
Me
H
Me
(III) (IV)
III > II > I > IV Bredt rule
5. A
Extended Cross
conjugation conjugation
6. A
O
(A) CH 3 CH CH3 Most Stable
+
non-bonding e Bonding
CH 3 CH 3
+ + +
(B) CH 3 CH (C) CH 3 CH CH3 (D) CH3 C
CH 3
7. A
(1) Me C H2 is more stable than MeO C H2
8. D
(A) O Br O Br
..
..
(B) O
.. O
Br Br
394-Rajeev Gandhi Nagar, Kota
GOC 7
..
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
10. D
3 2 2
sp sp sp
11. B
CH2
Cl C Cl > > CH3CHCH3 > CH 3CCH3
| |
Cl +I groups CH3
-I groups
+I groups
12. B
1 1 1
2 2 2
3 3 3
4 4 4
O O
Longest C O Bond.
14. (B)
C2H6 > C6H6 > C2H4 > C2H2
15. B
16. (C)
17. (A)
(B) aromatic
O
O
aromatic
21. B
Aro.
Aro.
(I) (II) (III) 7eqt. st.
+5eqt.st.
most stable
more Rotational
Aro. Aro. energy.
unstable
least Rotation energy
22. B
23. (D)
NH NH
aromatic
24. (C)
CH 3 CH3 CH3
HO HO OH HO OH
HO OH HO OH HO + OH
O OH OH
Stable carbocation
Tropylium C+
25. C
26. A
Cl
Tropylium
Q.Aro.
(A) I > V > IV > III > II
27. B
28. C
N
(I) (II) (III) ..
O |
N
H
Its Resonating structures are Neutral & Benzene like Resonance
So, maximum aromatic character.
29. C
+
(I) CH 3COOH (II) CH 3COONa (III) CH3CONH2
O O O
CH 3C CH3C CH 3C
+
OH O Na 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 O O
(I) (II) (III) (IV)
more resonance
so max. Resonance energy
31. B
Aromatic system has higher resonance energy than non aromatic
32. B
(due to hyper conjugation)
EXERCISE-2 LEVEL II
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.
+
:
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GOC 12
: :
5. (a) :N N N: and :N=N=N:
:
:
Resonance form
:
: :
(b) :N N N : and :NN=N:
It is not Resonance form due to different number of .p and B.p.
: :
: :
: :
: :
O O
C C
:
OH H OH
6. (a) H
:
:
R.S. (1) R.S. (2)
[neutral] [Charged]
(b)
N N
:
CH 2 CH2
(c)
R.S. (1) R.S. (2)
[Aromatic] [Anti Aromatic]
CH2 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)
:
CH3 CH C N: CH3 CH = C = N:
7. (a)
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.
O O
O
CH3 C CH = CH CH 3
R.S. (3)
Stability order
R.S. (3) > R.S. (2) > R.S. (1)
O O O O
(c) 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.
NH2 NH2
:
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GOC 14
COO O
and
(b)
eqt R.S.
So it has higher Resonance energy
and
and CH2 = CH CH 2
(b) Anti Non -Aro
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
O O
(c) and
Cross Extended
conjugation conjugation
(e) and
Cross Extended
Conjugation Conjugation
11. HN=C=O
HOC N
H H
N=C=O
OC N
12. (A)
Br
Cl
2SbCl5
+2 2SbCl 5
13. (B)
Cl
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GOC 16
H K
14. (B)
H
+
Bu Li P
Base
abstract the H
CH3 CH3
CH3 CH3
PhLi
Strong Base
CH3 CH3
CH2 CH2
Aromatic Antiaromatic
Br
16. (I)
Bridge headed
carbon +ve charge
unstable
Br
+ve charge
stablize by
resonance
(II)
Br Quasi
(III)
Aromatic
Br
(IV) 3o carbocation
17.
HClO 4
ClO4
|| |
O OH
|
O
18.
AgClO4
Cl ClO4
Ag ClO4
..
N O
..
|
(A) (B) (D)
N
N
6e 6e 6e
H H O O
KH HBr
20. (A) (B)
+ H
H H
H I
(C)
Tropylium
(Aromatic)
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GOC 18
CH 3
CH3C
21. (i) (a) CH CH (b) CH CH CH (c)
3 2 3 2 3
CH3
3H 6H 9H
CH3
(c) (d)
It stable
In chair
on boat form
(xi) (a) (b) CH 2=CH (c) CH3CH2
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) CH 3=CH2
more E.N. have free Radical then It will less stable In compare to free Radical on less E.N.
CH2 CH2
CH 2
CH2
CH 2 CH2
CH 2
CH 2
CH2 CH2
OH
(iii) (a) (b) (c)
OH OH
+M, I I
+M
CH2
CH 2
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GOC 20
O O O
CH2 CHCH
2 2
SP carbon
2
SP2carbon
CH2
CH2
CH2 H
C H
H
H C H
H
(xii) (a) H (b) C H (c)
Reso
Reso Reso +I
+I H
+hyper hyper
conjugation
CH 2 CH 2 CH2
: Br :
Reso. :
O
(c) C
and CH3 CH2 Cl
: :
CH3 Cl
Reso.
CH 3
(e) and
CH2 CH3 C2H5
(b) CH 3 C CH and HC CH
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GOC 22
O O
(d) C and C
:
:
H2N NH2 CH3 NH2
O O
(e) C and C
:
Cl Cl CH 3 Cl :
:
Both Side Reso. Single Side Reso.
O O
(f) C and C
:
:
:
HN
2
NH 2 H NH2
NO2
5
1 3
26.
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 or
27. (a) (b)
(c) or
28. A + 3H2 Pd / c
B D
(D)
1
HOH
stability of isomeric Alkene
(II)
(A)
Reso
(C)
CH3 CH3 O
(b) CH3 and CH3 (C) and
Reso
1 1
HOH HOH
stability of isomeric Alkene stability of isomeric Alkene
CH3 H CH3
CH3
C=C C=C
(d) H CH 3 and H H
Trans-form cis-form
1
HOH
stability of isomeric Alkene
CH 3 CH3
(e) CH2=CH CH and CH 2 = C
CH 3 CH 2 CH3
1
HOH
stability of isomeric Alkene
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GOC 24
(iii) (iv)
(iii)
31.
(d) CH 3 and
1
HOH
stability of isomeric Alkene
32.
HOC number of Carbon in hydrocarbon
1
HOC
Stability of isomeric Alkene
(c) CH 3 C = CH CH CH3
CH3 CH3
CH3
(d) CH 3 C HC = CH CH3
CH3
CH3 CH3
(d) (e)
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GOC 26
more repulsion
1
HOH
stability of isormeric Alkenes
a
HCH2
d
HCHCHCCH3
c b
He H H
35.
CH2
f H
1
CH 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
394-Rajeev Gandhi Nagar, Kota
GOC 27
The conjugate base of compound (b) is most stable due to aromaticity (i.e. )
CH3 CH3
OH H3C OH H3C OH OH
39. (A) (B) (C) (D)
CH 3 H3C NO2 H3C
O2N
NO2 I CH3 M NO2
I I
Maximum acidity (C). Ans. (C)
COOH COOH
COOH COOH
OH
40. (A) (B) (C) (D) (ortho effect)
OH
OH +I
+M
(most acidic)
Compound (B) is less acidic due to (+M) effect of OH group because it is present on pera
position.
OH OH HO OH
OH
41. (I) (II) (III)
O O O O
O O
O O O
O O
O
O
O
O
O
O
4 eq. Aromatic R.S. Non aromatic
1
acidity Pk acidity (ka) order = I > II > III
a
Pka order = III > II > I
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GOC 28
42. (1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Benzoic acid
OH COOH
H C OH
C2H5OH
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.
44. (A)
(R) Aromatic Compound
(B)
(S) Anti Aromatic Compound
:NH
(C)
(R) Aromatic Compound
:
N
H
H
N
:
sp3 carbon
2
(P) Hybrid state of each atom sp
(D) (Q) Anti Aromatic
:
46. (A) NH
(R) Resonance
(P) Resonace
(C)
: :
O (R) Aromatic
(C) or
CH2CH3 CHCH3
(D) or
Reso.
(P) First is more stable than second
(R) Not resonating structure of each other.
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GOC 30
CH3
+I CH3 CH2 O
More stable 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
(d) C6H5SO3
[I order C R > Ph]
O
(More the resonating structures, more the stability)
d>a>c>b
CO
C O CO
O
3 O 2 O sp
sp sp (more-I)
Stability = C > b > a
acidity = c > b > a
CH2 COOH
CH2 COOH
COOH
COOH H+
CH2
COOH COOH
H+ H+
COO
CH2 C O
(iii) (a) (b) (c)
COO
CH2 O
COO CH2 C O
COO
O
[a > b > c]
O O
3. (a) Cl CH2 C O H H+ Cl CH 2 C O - (one -I group)
O O
(b) Cl CH2 C O H H+
Cl CH2 C O (two -I grop)
Cl Cl
Cl O
Cl O
Cl C C O H H+
(c) Cl C C O (Three I groups)
Cl
Cl
(most stable)
Ans. c>b>a
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GOC 32
O O
(ii) (a) CH 3 CH 2 CH C O H H+ CH3 CH2 CH C O
F F
F O F O
O
(c) CH2 CH2 CH2 C O H H+ CH2 CH2 CH2 C O
F F O
In this type of case are see "DNP" rule.
Distance Power
Number
Acidic strength = a > b > c
O O
(iii) (a) H+ NO2 CH2 C O
NO2 CH2 C O H O
O O
(b) F CH2 C O H H+ O
F CH2 C O
O O
(c) H+
Ph CH 2 C O H Ph CH2 C O
O
O O
(d) CH3 CH2 C OH H+ CH3 CH 2 C O
Acidic Strength : a > b > c > d
:
:
:
NO2 Cl CH 3
(strongel acid)
O O O
NO2 Cl CH 3
I I +I
(most stable
conjugate base)
Acidic strength = a > b > c
:
:OH
:
:
:O H :O
:
:O H
:
:
:OH :O H :O H
H+ H+ H+ H+
O
O O O
CH3
CH 3
stability of Conjugate base : d > b > c > a
acidity order : d > b > c > a
:
:O H
:
:OH :
:O H
:
P :O H
N
5. (i) (a) O (b) O (I) (c) (d)
N N
(M) Hydrogen Bonding O O
O
(M)
Acidity order = c > a > b > d
:
:
:
:O H :O H :O H :OH
O
N NO2 O2N NO2
O
(ii) (a) (b) (c) (d)
NO2 HBonding NO2 NO2
M (M) I I
Acidity order = d > c > a > b
O
O
COH
COH
CH3
H+
O H+
6. (i) (a)
(b) O
CO
CO
CH 3
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GOC 34
O
.. O O
CO
.. H ..
CO
.. H COH
..
O
.. Me
..
:O
.. Me O
.. Me
O O O
(iii) (a) (b) CO
(c) CO
CO
O Me
O Me
+I Ortho effect max. acidity
O Me
(+M)
Acidity order c > b > a
O O O
COH COH C OH
NO2
(iv) (a) (b) (c)
NO2
I Ortho effect
N
O O
M
I
Acidity order = c > a > b
OH OH OH OH
OH OH OH OH
O Me
(iii)(a) (b) (c) (d)
+M O Me
O Me
I
M
acidity with drawing tendency of group.
so (b) max. acidity.
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 COOH
acidity stablity of CB
COOH OH OH
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GOC 36
OH OH OH
NO2 CH3
M +I
I +H
NH 2 (3)
CH3 NH2 CH3 NH
H NH
(2)
H
(1) CH3 CH2 CH2 CH2 CH2 NH2
CH3 CH2 CH2 CH2 CH2 CH2 NH
acidity stability of conjugate Base
stability order = 2 > 3 > 1
acidity order = 2 > 3 > 1
Pka = 2 < 3 < 1
O
10. (a) CH3 CH2 Br & CH3 NO2 (b) CH3 C CH3 (C) CH3 CHO
+I
(1) CH3 CH Br & CH3 C CH2 CN CH3 NO2
O
O
(2) CH2 NO2 (1) (1) CH 2CH
CH2 C CH3
I ||
O
(2) is stronger acid (2) CH 3CCHCN (2) CH NO
2 2
|| I
O
(2) > (1) (2) > (1) (2) > (1)
OH
OH
(b) as (2)
O = C CH3
CH3
M +H
So (2) is weaker acid
SH OH S O S O
So is weaker acid
O O
COOH or
|| O
+ ||
N C OH
O
12. (a)
COO
O2N COO
M
acidity M effect
so (2) is more acidic
(b) CH3 CH2 CH2 OH or CH3 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
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GOC 38
1
13 (i) Basicity Stability of anion
.. .. ..
(iii) R NH2 Pn NH 2 R C NH2
.p. localised .p. delocalised
(more basic) (weak base) O
.p. more delocalised
(least base)
basicity order a > b > c
(iv) In gas phase basicity (+I) effect.
Basicity order
NH3 < Me NH 3 < 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 : 2amine > 1amine > 3amine > NH3
O
14. (i) .. ..
NH NH N
Me
.p. localised
.. .p. delocalised
NH2 ..
NH2
NH
..
(ii)
.p. localised
(2 amine)
1amine
(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
.. .. ..
15. (i) (a) CH3 CH2 NH2 (b) CH3 CH = NH (c) CH3 C N
sp3 sp2 sp
Least electronegative. most electronegative
most basic least basic.
order a > b > c
.. ..
(ii) (a) CH3 C NH2 (b) CH3CH2 NH2
O Lone pair localised
least basic, l.p. of
nitrogen is delocalised.
.. .. ..
(c) CH 3 C NH 2 (d) NH 2 C NH 2
NH
.. NH
More basic due to Most basic, due to more
delocalisation of only delocalisation of l.p.
one l.p.
* 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.
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GOC 40
O
..
NH C CH 3
basic.
..
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
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.
16 (i)
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
394-Rajeev Gandhi Nagar, Kota
GOC 41
NH2 NH2
NH2 Ortho effect
NO2
(iii) (a) (b) (c)
NO2
+I
NO2
M
Me Me
N Me Me
N Me Me
N
SIR
OMe
(v)
OMe
+M OMe I
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.
1
18. (i) Basicity
E.N. of anion
Order of E.N.
CH3CH2 < CH2 = CH < HC C < CH3CH2O
(b) (a) (d) (c)
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GOC 42
.. ..
(ii) (a) NH 2 (b) CH 2 NH2
l.p. is in conjugation
l.p. localised, most basic
only with benzene ring.
..
(c) NH2 (d) C NH2
O
NO2
Ortho effect l.p. is in conjugation with
C group. Which is most
O
with drawing.
O CH3 CH3
Nb
H2N C H2C CH2 NH C CH 3
c
NH
19. a
N
CH3 d CH3
22.
..
N
H
This lone pair very much delocalised because of getting Aromaticity so do not donate lone
pair so it is least basic.
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
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GOC 44
(b) Puridine or Pyrrole
..
N
.. N Delocalised lone pair 1>2
Localised lone pair H so least basic.
..
(c) CH3C N or CH3CH2 NH2
sp nitrogen so less basic sp3 Nitrogen 2>1
..
25. (a) H2O or H3O+
(2) +ve charged spcie is weak base.
(b) H2S, SH, S2
(1) Neutral so weak base More ve charge more donating tendency.
(c) Cl, SH
(1) S Cl E.N. size small
More sable
less basic
(d) F OH NH2 CH3
CH3 NH2 OH F
Size
(1) 'F' more electronegative so do not donate the pair of e so less basic.
(f)
OH SH SeH
Big size
(3) ve charge stable, So weak base.
1
Basicity
Stability
.. ..
NH2 NH2
26. (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
Sove 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
394-Rajeev Gandhi Nagar, Kota
GOC 45
.. .. .. ..
NH2 NH2 NH2 NH 2
CH3 NO2
27. (a) (i) (ii) (iii) M (iv)
NH2 NH2 ..
NH2 CH2 NH2
CH3
(b) (i) (ii) (iii) (iv)
CH 3
Ortho effect +I CH3
+H
1<2<3<4
28.
(a) (i) OH (ii) CH3COO
(iii) Cl
>
Stability Cl
CH3COO > OH
Basicity order : OH > CH3COO > Cl
1 2 3
(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 CH 2 NH 2
sp
Basic strength : 3 < 1 < 2
..
NH C6H5
NH2 NH2
NH 2 NH 2 NH 2
Cl
(b) (i) (ii) (iii)
Cl
Ortho effect More I Cl
Less I
1 <2<3
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GOC 46
30. (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
.. H
NH2 NH2 N
31. (a)
More resonance
2>1>3 least basic
H
N
..
NH N:
(b)
Localised l.p.
l.p. Delocalised
1>2>3
..
HN N NH NH
(c)
Participate in
resonance so
least basic
6
5 7
5 N 5
4 6
4
N1
8
32. N N N :N H N 4 2
1 9
3 1 3 N
2 3
2 H
Pyrimidine Purine
Imidazole
Localised lone pair
Protonation takes Three basic 'N'
of N, 6e ,aromatic
place on N1 N1, N3, N7
+
1 N NH
3
2
6e
aromatic
So (A), (C) & (D) are aromatic.
2. D
As the bulkiness increases, nucleophilicity decreases.
3. B
Lone pair of N is not in conjugation with benzene ring.
4. C
5. D
6. C
7. A
8. 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
9. D
Reaction with bulkier nucleophile will be slower.
10. B
e withdrawing groups increase the acidity and e donating groups decrease the acidity.
11. C
Due to less steric effect and more +I effect and effective solvation.
12. D
Nitro group decreases the e density at benzene ring.
13. B
14. B
e withdrawing groups stabilise and e donating groups destabilise the carbanions.
15. D
Correct order of increasing basic strength is
RCOO HC C NH R
16. A
17. A
18. D
19. B
Benzylic > allylic > 1 alkyl
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GOC 48
20. B
(a) (b)
(c) (d)
21. C
(least Basic)
Order of basic strength in aqueous solution 2 > 1 >3 amine > aniline.
1
Basic strength Kb pk
b
(CH3)2NH is most basic so it has smallest pKb.
SO3H
+
CH3COONa (excess)
(aq. solution)
SO3Na
Me
Me
SO3H SO3Na+
O O
+
+ CH3 C O Na + CH 3 C OH
Me Me
2. C
l.p l. p repulsion
:
: :
H2C = CH CH CH O CH3
.. SiMe3
|
N N
3.
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.
4. C
Cl
C
H H
H
Vector addition of this compound is more
5. D
SO3H SO3Na
NaHCO3
+ H2CO 3 H2O + CO2
+
OH ONa
NaHCO3
+ H2CO 3 H2O + CO2
NO2
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GOC 50
6. C
OH
OH OH OH
OH
(i) (ii) (iii) (iv)
OH
OH
7. A
Repulsion
O
N
O
8. D
OH
9. B
eg. CH3 CH = CH2
H H
H C CH = CH2 H C = CH CH 2
H
H
10. D
ct
fe
I ef
+
: :
(i) +I O O (ii)
ct
:
fe 2 carbocation
ef
: :
1 carbocation
OH OH COOH COOH
Cl CH3
eqt.R.S. eqt.R.S.
O O COO COO
Cl CH 3
I +H
12. B
incomplete octact
H2C N = N
(iii) (iv) H 2C N = N
P-orbital
-ve on less E.N. atom
Resonance
I > III > II > IV
13. 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.
14. 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).
15. 4
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
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GOC 52
16. C
NO2 OH CH3
NO2 OH Intramolecular
CH3
I H-Bonding
M, I
17. 6
CH 3 CH2CH 3
18. B
OH OH COOH COOH
Cl CH3
eqt.R.S. eqt.R.S.
O O COO COO
Cl CH 3
I +H
19. B
is anti aromatic.
21. 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.
22. 9
O O
(1) (2)
O O
(3) (4)
O O O
(5) (6) (7)
O O
(3) (8)
O
(9)
23. 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 (I)
(M)
OH OH
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