1 GENERAL ORGANIC CHEMISTRYI - I

C-LS
Level-II
C-123 To C-129

Lecture Planning & Flow

No. Lecture Contents Homework of this lecture
Breaking & Forming of Bonds, Abhyaas – I
Electron Displacement in Organic Molecules, (Himanshu Pandey) Page:1 (Q-1, 2)
M S Chauhan Page:1 (Q-1 to 11)
Inductive Effect, Applications of Inductive Effect. Yes No
II Mesomerism Effect, +M Effect, -M Effect,
Abhyaas – II (Himanshu Pandey)
Resonance, Rules for Drawing Valence Bond Page:1 (Q.5-7, 29-30, 39-46), Page: 9 (Q.3-41)
Resonance Structures. M S Chauhan
Page:13 (Q.61,85,165-172)
III Electromeric Effect, Hyperconjugation, Yes No
Effects of Hyperconjugation.
Abhyaas–III (Himanshu Pandey)
IV Reactive Intermediates, Carbocations, Page:1 (Q.3-4,14-28), Page: 17 (Q-42-68)
Formation of Carbocations, Stability of M S Chauhan (Elementary)
Carbocations. Page:45 (Q-1-15)
Yes No
V Carbanions, Formation of Carbanions,
Stability of Carbanions. Abhyaas– IV (Himanshu Pandey)
Page:15 (Q.31-38), Page: 37 (Q.153-205)
VI Free Radicals, Radicals of Formation, Radicals (M S Chauhan Elementary)
Page:47 (Q-1-103), Page: 64 (Q1-18)
of Stability, Carbenes, Formation of Carbenes, Yes No
Stability of Carbenes, Nitrenes, Arynes,
Formation of Arynes, Stability of Arynes. Abhyaas– V (Himanshu Pandey)
Page:46 (Q.1-55)
VII
VI Acid & Base, Stability of Acid & Base. (M S Chauhan) Page:23 (Q.120-164)
Yes No

Abhyaas– VI (M S Chauhan Elementary)

Page: 67 (Q.19-29), Page: 68 (Q.1-37)
Page: 77 (Q. 1-40)
Has the student completed the homework of the previous Yes   No  
lecture ?
Abhyaas– VII (M S Chauhan Elementary)
Page:83 (Q.41-92), Page: 91 (Q.1-19)
Roll No. STAMP Yes   No  
Module Yes   No  

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CHEMISTRY 2

ABHYAAS - II
LEVEL - II

Q-1 Show the direction of Inductive-effect in following compounds.

CH 3 COONa
(P) (Q)
COOH OH

CH = CH2
COOH
(R) (S)
NaO
CCH

Soln:

Q-2 Arrange following compounds in decreasing order of their dipolemoment.

I II III IV

(x) CH3—CH2—NO2 CH3—CH2—NH2 CH3—CH2—F CH3—CH2—CN

(y) CH3—CH2COOH CH3—CH2—OH CH3—CH2—Cl CH3—CH2—NH2

n
Sol :

Q-3 Select correct statement about I effect.

(A) I effect transfers e¯ from one carbon atom to another.
(B) I effect is polarisation in  bond.
(C) I effect creates net charge in molecule.
(D) I effect is distance independent.
n
Sol :

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 3 GENERAL ORGANIC CHEMISTRYI - I

Q-4 Which of the following has incorrect direction of Inductive effect.

CH3
O O
-
C – OH C O
(A) (B) (C) (D) CH3 C CH2 CH3
O
CH3

Soln:

Q-5 Which of the following species has a pyramidal shape-


(A) CH3+ (B) BF3 (C) CH3– (D) C H 3

Soln:

Q-6 In which of the following compounds is hydroxylic proton the most acidic -
F
(A) O (B) I O
H H
(C) O (D) O
H H
F F
Soln:

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CHEMISTRY 4
Q-7 Correct arrangement of the following acids in correct Ka order is :-

(I) H3N—CH2—COOH (II) NC—CH2—COOH


(III) H3C—CH2—COOH (IV) OOC —CH2—COOH

(A) I > II > III > IV (B) II > I > III > IV (C) I > III > II > IV (D) IV > III > II > I

Soln:

Q-8 Which of the following orders of acid strength is correct :-

(A) RCOOH > ROH > HOH > HC CH (B) RCOOH > HOH > ROH > HC CH

(C) RCOOH > HOH > HC CH > ROH (D) RCOOH > HC CH > HOH > ROH
Soln:

Q-9 Which of them is false for order of – I effect

 
(A) –F > –Cl > –Br > I (B) –NR3 > –NH3 > –NO2

(C) –OCH3 > –OH > –NH2 (D) > –C  CH > H

Soln:

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 5 GENERAL ORGANIC CHEMISTRYI - I

Q-10 The order of basicity of halides is :

– – – – – –
(A) Cl < Br – < I < F (B) F < I < Br– < Cl
– – – – – –
(C) I < Br – < Cl < F (D) Cl < F < I < Br –
Soln:

Q-11 Which of the following molecule has longest C=C bond length -

(A) CH2=C=CH2 (B) CH3–CH=CH2

CH3
(C) CH3–C–CH=CH2 (D) CH3–C=CH2
CH3 CH3
n
Sol :

H O
Q-12 In the reaction CH3CN 
3
CH3COOH
heat

the hybridization state of the functional carbon changes from

(A) sp3 to sp2 (B) sp2 to sp3 (C) sp to sp2 (D) sp2 to sp

Soln:

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CHEMISTRY 6
Q-13 The increasing order of base strength of Cl –, CH3COO–, —
OH and F— is :

(A) Cl– < F— < CH3COO– < —

OH (B) Cl– > F— > CH3COO– > —
OH

(C) CH3COO– < Cl– < F— < —

OH (D) None of these
Soln:

COOH

Q-14 , pKa value of the compound decreases if X is :-

(A) –NO2 (B) –NH2 (C) –OH (D) –OCH3

Soln:

Q-15 Hybridisation of arrow headed 'C' is

(A) sp2 sp3 (B) sp3 sp3 (C) sp2 sp2 (D) sp3 sp3d
Soln:

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 7 GENERAL ORGANIC CHEMISTRYI - I

ABHYAAS - II
LEVEL - II

Q-1 Show why the phenolate ion, C6 H 5 O – , has a greater resonance stabilization than phenol, C 6 H 5 OH .
Soln:

Q-2 H3C CH2

OH
Write resonance structure of the given compound.
n
Sol :

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CHEMISTRY 8
Q-3 Which of the following compounds have delocalized electrons ?
O
||
a. CH 2  CHCCH 3 g.

b. h. CH3CH2NHCH2CH = CHCH3

c. i. CH3CH2NHCH = CHCH3

d. j.

e. CH2=CHCH2CH = CH2

CH3
f. k. CH3CCH2CH = CH2
+

Soln:

Q-4 The central carbon-carbon bond in 1, 3-butadiene is shorter than that of n-butane. Why ?
Soln:

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 9 GENERAL ORGANIC CHEMISTRYI - I
Q-5 In which of the following delocalisation of -electron is possible.
(A) CH2 = CH – CH2 – CHO (B) CH2 = CH – CH = O
(C) CH3 – CH – CH 3 (D) CH2 = CH – CH2 – CH = CH2
|
OH
Soln:

Q-6 Which of the following compounds have delocalisation of -electrons ?

CH2NH2 NH2

(A) (B)

(C) CH3CH2NH CH2 CH = CH2 (D) CH2 = CH – CH2 – CH = CH2

n
Sol :

Q-7 Which of the following species have conjugated ?

SH
:

(A) (B) (C) CH2 = C = CH – NH2 (D) All of these

Soln:

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CHEMISTRY 10
Q-8 Which of the following is not a pair of resonating structures ?
  ..
(A) H  C  N H ; H  C  N H

(B) CH3CH = CHCH3; CH3CH2CH = CH2

-
(C) CH3 – C = CH – C – CH 3 ; CH3 – C – CH – C – CH3
| || || ||
-
O O O O

(D) ;

Soln:

Q-9 Which of the following is not a permissible resonating structure :

+ - + - + ..-
(A) CH2 N O (B) CH2 N O (C) CH2 = N = O (D) CH2 N O
| |
CH3 CH3 CH3 CH3

Soln:

Q-10 Which of the following resonating structure will contribute minimum to resonance hybrid.

O O¯
–
O¯
|| | | +
CH3 – C – OCH3 CH3 – C – OCH3 CH3 – C = OCH3
+
I II III
(A) I (B) II (C) III (D) All structure are equally stable

Soln:

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 11 GENERAL ORGANIC CHEMISTRYI - I
Q-11 Which of the following resonating structure contributes equally to the resonance hybrid.
 
(A) CH3 – C – CH  CH – CH3  CH – C  CH – C H – CH
| 3 3
|
CH3 CH3

+
(B) CH 3 – C – NH 2  CH3 – C = NH2
||
O |
O-
-
O O
(C) CH3 – C  CH3 – C
-
O O

+
(D) CH2 = CH – CH = O  CH2 – CH = CH – O-
Soln:

Q-12 Which of the following molecule has longest C=C bond length ?
(A) CH2 = C = CH2 (B) CH3 — CH = CH2

CH 3
|
(C) CH 3  C  CH  CH 2 (D) CH 3  C  CH 2
| |
CH 3 CH 3

Soln:

Q-13 The decreasing order of bond length of C = C bond in the following compounds is:
H3C

H3C
I II III IV
(A) II > I > IV > III (B) III > I > II > IV (C) IV > II > I > III (D) IV > I > II > III
Soln:

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CHEMISTRY 12
Q-14 Although phenoxide ion has more number of resonating structures than benzoate ion, beznoic
acid is a stronger acid than phenol. Why ?

Soln:

Q-15 Formic acid is considered as a hybrid of the four structures


O O O O

H– C–OH  H– C = O H  H–C–O–H  H–C–O–H
 

I II III IV
Which of the following order is correct for the stability of the four contributing structures.
(A) I>II>III>IV (B) I>II>IV>III (C) I>III>II>IV (D) I>IV>III>II
Soln:

Q-16 Stability of :

CH3
(I) CH 3 –CH=CH–CH 3 (II) CH3– C = C – CH3
CH3

(III) CH3– C = CH2 (IV) CH3– C = CH – CH3

CH3 CH3

in the increasing order is :

(A) I<III<IV< II (B) I<II<III<IV (C) I<IV<III<I (D) II<III<IV<I
n
Sol :

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 13 GENERAL ORGANIC CHEMISTRYI - I

Q-17 (I) (II) (III)

Compare carbon-carbon bond rotation across I, II, III.

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
Soln:

Q-18 C—C and C=C bond lengths are unequal in :

(A) Benzene (B) 1,3 buta-di-ene
(C) 1, 3 cyclohexa-di-ene (D) None
Soln:

Q-19 Which species is not aromatic :

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

N N
:

Soln:

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CHEMISTRY 14

ABHYAAS - III
LEVEL - II
Q-1 Write the number of hyperconjugable hydrogen atoms of following species :

CH—CH3


(a) (b) CH3— C H—CH2—CH3

CH=CH2

CH3
(c) C=CH—CH3 (d) CH3—CH=CH—C2H5
CH3

Soln:

Q-2 Write the stability order of following alkene :

H CH3
(I) (II) CH3–CH=CH–CH3 (III) C=C
CH3 CH3

CH 3 CH 3
| |
(IV) CH 3 — C — CH  CH — C — CH 3
| |
CH 3 CH 3

Soln:

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 15 GENERAL ORGANIC CHEMISTRYI - I

Q-3 Inductive effect involves :

(A) Delocalisation of  - electrons
(B) Partial displacement of  - electrons
(C) Delocalisation of  - electron
(D) Displacement of lone pair electrons.
Soln:

Q-4 In hyperconjugation there is overlap between :

(A) p- and -orbitals (B) 2  - orbitals (C) d-and--orbtial (D) -and - orbitals
Soln:

Q-5 Hyperconjugation involves.

(A) Delocalisation of -electrons with an adjacent -bond.
(B) Delocalisation of -electrons with an adjacent triple bond.
(C) Delocalisation of -electrons with an adjacent double bond.
(D) All are true
n
Sol :

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CHEMISTRY 16
Q-6 Hyperconjugation phenomenon is possible in :

CH3

(A) CH3 – C – CH = CH2 (B) CH2 = CH2

CH3

(C) C6H5 – CH = CH2 (D) CH3 – CH2 – CH = CH2

Soln:

Q-7 Discuss the hybridization of carbon atoms in allene (C 3H4) and show the -orbital overlaps.
n
Sol :

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 17 GENERAL ORGANIC CHEMISTRYI - I

Q- 8 In which of the following molecule all the effect namely inductive, mesomeric & hyperconjugation operate:

(A) —Cl (B) —CH3

CH3

(C) —COCH3 (D)

CH3

Soln:

Q-9 Which of the following s-bonds participate in hyperconjugation :

I V
H
H CH3
II
H IV
III
(A) I and II (B) I and V (C) I and V (D) III and IV
Soln:

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CHEMISTRY 18

ABHYAAS - IV
LEVEL - II

Q-1 For each pair of ions, determine which ion is more stable.
   
(A) CH3–CH–CH 3 and CH3–CH–OCH3 (B) CH2=CH–CH–CH3 and CH2=CH–CH2–CH2
(I) (II) (I) (II)

– –
(C) CH2–CH3 and CH2–CN (D) and
(I) (II)

(E) CH3–N–CH3 and CH3–CH–CH 3

CH3–C–CH3 CH3–C–CH3
 
(I) (II)
Soln:

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 19 GENERAL ORGANIC CHEMISTRYI - I

Q-2 Which of the following carbocation is more stable and why ?


CH2

(A)

+ I effect of three – CH3 group and 10 hyperconjugation structure.

   
C H2 C H2 C H2 C H2

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

OCH 3 NO 2 Cl

+
CH3 CH3 + CH3 CH2
(q) (A) (B) (C) (D)
+
+

+ +
+
(r) (A) CH2 (B) (CH3CH2)2 CH (C) (CH3CH2)3 C + (D) CH CH3

Soln:

Q-3 Arrange the following carbanions in decreasing order of stability :

- - -
- CH2 CH2 CH2
CH2 | | |
|

| | |
CH3 NO2 OCH3
I II III IV

(A) III > I > IV > I (B) III > II > I > IV (C) I > III > II > IV (D) III > I > II > IV
Soln:

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CHEMISTRY 20
Q-4 The most unstable carbocation is
   
(A) CH3 C H 2 (B) Cl – CH2 – C H 2 (C) C H 2 – CHO (D) C H 2 – O – CH3

Soln:

Q-5 Electrophile is :
(A) H2O (B) NH3 (C) AlCl3 (D) C2H5NH2
Soln:

Q-6 Most stable carbocation is :-

   
CH2 CH2 CH2 CH2

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

Cl NO2 OCH3

Soln:

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 21 GENERAL ORGANIC CHEMISTRYI - I

Q-7 Consider the following carbocations

   
(a) CH3O– –CH2 (b) –CH2 (c) CH3– –CH2 (d) CH3— C H 2

The relative stabilities of these carbocations are such that :-

(A) d < b < c < a (B) b < d < c < a
(C) d < b < a < c (D) b < d < a < c

Soln:

Q-8 Which of the following carbonium ion is most stable

(A) Ph3C+ (B) (CH3)3 C+ (C) (CH3)2 CH+ (D) CH2 CH—CH2+

Soln:

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CHEMISTRY 22
Q-9 Match List- I with List- II and select the correct answer using the codes given below -
List-I (Stability) List -II (Reason)

H3C CH3
C
(A) > CH3+ (1) Inductive effect

 Br
(B) H3C–C < CH3– (2) Resonance
CH3

 CH3
(C) H3C–C > H3C–CH2+ (3) Hyperconjugation and resonance
CH3

• H3C •
CH2 CH2
(D) > CH3 (4) Hyperconjugation and inductive effect

Codes :
(A) A - 2 ; B - 3 ; C - 4 ; D - 1 (B) A - 3 ; B - 1 ; C - 4 ; D -2
(C) A - 4 ; B - 3 ; C - 1 ; D - 2 (D) A - 3 ; B - 4 ; C - 2 ; D - 1
Soln:

H

CH3–C–CH2
1,2 shift
Q-10 A (Major) ; Here A is :

CH3
 
CH3–C–CH3 CH–CH2
(A) (B)

H
(C) CH3–C–H2C– (D) CH3–C= CH2

Ph

Soln:

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 23 GENERAL ORGANIC CHEMISTRYI - I

Q-11 The maximum probability of proton loss is in the case of :

H H
  H 
(A) CH 3 – CH 2 (B) CH3– C – CH3 (C) (D) (CH3)2C – CH2
CH3 

Soln:

Q-12 Select the least stable one :

H3C H3C 

(A) CH3 – CH2 (B) CH3– CH2– CH2 (C) CH– CH2 (D) H3C C – CH2
H3C H3C

Soln:

Q-13 Energy of activation is lower for which reaction :

   
(A) RCH 2 OH 2  R C H 2 (B) R 2 CH OH 2  R 2 C H
 
(C) R 3 C OH 2  R 3 C (D) all have same Eact.

Soln:

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CHEMISTRY 24
Q-14 The precursor carbocation to the product in the following reaction is :
H

C6H5 H C6H5
OH H


(A) C6H5 (B) C6H5  (C) either of the two (D) none of the two

Soln:

Q-15 Which of the following ion is formed in the following reaction :

H
OH O



(A) 
(B)
OH OH


CH2
(C) (D) All of three
OH

Soln:

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 25 GENERAL ORGANIC CHEMISTRYI - I

OD
D NaOH
Q-16 CO2
[Intermediate]
D
P. Product is :

OD OD
HOOC D DOOC D
(A) (B)

OH
DOOC D
(C) (D) Reaction not possible

Soln:

Q-17 Which of the following intermediate is most likely to be formed during addition of HBr on crotonic acid :

CH3CH = CHCOOH + HBr(g)  CH3 CH–CH2COOH :

Br
 
(A) CH 3 CH 2 – C HCOOH (B) CH 3 CH – CH 2COOH
OH
(C) CH3CH=CH–C–OH (D) none of these


Soln:

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CHEMISTRY 26
Q-18 Which will give most stable cation upon strong heating :

CH2–Cl Cl
CH2
(A) (B) (Ph)3C–Cl (C) (D) CH
CH2–Cl

Soln:

Cl
Q-19 (A); Here (A) is :
—Cl
H


(A) (B) (C) 

(D)



Soln:

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 27 GENERAL ORGANIC CHEMISTRYI - I

Q-20 In which of the following case 'H' shift is more preferable than 'CH 3' shift :

CH3 CH3 H
 
(A) CH3–C–CH2 (B) CH3–C–CH–C–H
H CH3 H

CH3

(C) CH3–C–CH–CH3 (D) all
Ph

Soln:

Q-21 Which of the following will not give 1, 2, shift :

2
Hg

(A) (CH 3 )3 C — C H 2 (B) (CH3)3C CH—CH2

OH
(C) 
(D) all

Soln:

OH

Q-22 Which carbocation is more likely to be formed in the dehydration of H :


 
(A) (B) (C) (D)


Soln:

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CHEMISTRY 28

ABHYAAS - V
LEVEL - II

Q-1 In the following sets of resonating structure, label the major and minor contributors towards resonance hybrid.
– –
(a) CH3–CH–CN CH3–CH=C=N
(I) (II)
O O –
O O
–
(b) CH3–C–CH–C–CH3 CH3–C=CH–C–CH3
(I) (II)
–  
(c) CH3–CH–CH=CH–NO2 CH3–CH=CH–CH=N–O
(I)
O
(II)

 
(d) CH3–CH2–C–NH2 CH3–CH2–C=NH2

NH2 NH2
(I) (II)
n
Sol :

Q-2 The stability order of following carbocation is :

+
CH2

I II III IV
(A) I > II > IV > III (B) III > I > II > IV (C) IV > II > III > I (D) II > IV > III > I
Soln:

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 29 GENERAL ORGANIC CHEMISTRYI - I
Q-3 Following carbocation will rearrange to more stable carbocation ?

CH2



(A) CH2 (B)  CH3 (C) CH3 (D)  CH2

Soln:

Q-4 Write the increasing pkb values for following anions.

    
CH3 , NH2 NH2 , OH , F

Soln:

Q-5 Carbanion is a :-
(A) Base (B) Nucleophile
(C) Both (A) and (B) (D) None
Soln:

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CHEMISTRY 30
Q-6 Most stable carbanion is :-
(A) HC C (B) C6H5 (C) (CH3)3C—CH2 (D) (CH3)2C CH
n
Sol :

Q-7 Most stable carbanion is :

 
CH2 CH2

(A) CH 3 (B) CH 2  CH – CH 2 (C) (D)

NO2
Soln:

Q-8 Which of the following compounds yield most stable carbanion after rupture of (C1–C2) bond :

O O
(A) CH3—C—CCl3 (B) CH3—C—CBr3
1 2 1 2

O
(C) CH3—CH2—C—CI3 (D) None of these
1 2

Soln:

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 31 GENERAL ORGANIC CHEMISTRYI - I

ABHYAAS - VI
LEVEL - II

Q-1 Suggest the order of stability of the following

   
(a) C H 3 , C H 2Cl , C HCl 2 , C Cl 3
(b) CH – , CH Cl – ,CHCl – , CCl –
3 2 2 3
Soln:

Q-2 Most stable radical among following.

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

Soln:

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CHEMISTRY 32
Q-3 Arrange the following radicals in decreasing order of their stability.
CH3
|
• • •
(p) (I) CH 3
(II) CH3 – CH 2
(III) CH3 – CH (IV) CH3 – C •
| |
CH3 CH3
(A) IV > I > III > II (B) IV > III > II > I (C) I > II > III > IV (D) IV > III > I > II
CH3
CH3— C  + I effect and Hyperconjugation of three —CH3 group stablize 3º free radical.
CH3

• • •
(q) (I) CH2 (II) CH (III) C (IV)

Soln:

Q-4 Which one of the following results most stable carbon free radical :
• •
CH3 CH3
(A) (B)
• •
(C) (Ph)2C = C(Ph)2 CH3 (D) CH2 = CH2 CH3

Soln:

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 33 GENERAL ORGANIC CHEMISTRYI - I

Q-5 Following is true for stability between the two structures :

 
O O
(A) CH3–CH–CH=CH2 > CH3–C=CH–CH3

CH2
•
(B) CH2=CH–CH=CH–CH2• > CH2–C–CH–CH3

CH3
 
(C) CH2=C–CH2 > CH3–CH=CH– CH 2

O
(D) —O < CH3–C–O

Soln:

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CHEMISTRY 34

ABHYAAS - VII
LEVEL - II

Q-1 Write acidic strength order :

COOH COOH

NO2
NO2 NO2
(I) (II)

Soln:

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 35 GENERAL ORGANIC CHEMISTRYI - I
Q-2 Find the order of Ka of following compounds.
OH OH OH OH

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

NO2 Cl CH3 NH2

OH OH OH OH
F
(q) (A) (B) (C) (D)
F
F
COOH COOH COOH COOH

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

NO2 OH CH3
OH OH OH OH

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

F OH CH3

O O
(t) (A) S NH2 (B) NH2 (C) NH2 (D) NH2
C
O

Soln:

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CHEMISTRY 36
Q-3 Dimethylamine is stronger base than trimethylamine. Explain.
Soln:

Q-4 Write the order of Kb of following amines :

I II III
(P) (CH3)3N (CH3)2NH CH3NH2 (Gaseous phase)

(Q) (CH3)2NH CH3NH2 (CH3)3N (H2O as solvent)

(R) (C2H5)2NH (CH3CH2)3N C2H5NH2 (H2O as solvent)

Soln:

Q-5 What is the effect of electron releasing and electron withdrawing groups on the basic strength
of aniline.
n
Sol :

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 37 GENERAL ORGANIC CHEMISTRYI - I
Q-6 Write the decreasing order of basic strength of following compounds.

N N
N
H H
(I) (II) (III)

Soln:

Q-7 Write order of Kb of following species.

(p) (A)  CH2 – CH2 – NH2 (B)  ¯CH 2 – CH = CH2

(C) ¯CH 2 – C  N (D) ¯CH 2 – C  CH

(q) (A) C6H5CONHCH3 (B) C6H5NH2

(C) C 6 H 5  C  NH 2 (D) C6H5 – NH – CH3

||
O

(r) (A) C6H5NH2 (B) p-NO2 – C6H4NH2

(C) m–NO2 – C6H4NH2 (D) C6H5CH2NH2

Soln:

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CHEMISTRY 38
Q-8 Among the following compounds, the strongest acid is :
(A) HC  CH (B) C6H6 (C) C2H6 (D) CH3OH

Soln:

Q-9 Order of Ka of following acids.

+ -
H3N – CH2 – COOH NC – CH2 – COOH H3C – CH2 – COOH OOC – CH2 – COOH
(I) (II) (III) (IV)
(A) I > II > III > IV (B) II > I > III > IV
(C) I > III > II > IV (D) IV > III > II > I

Soln:

Q-10 Find the strongest acid among the following compounds.

(A) CH3 CHCOOH (B) CH3–CH – COOH
NO Cl

(C) CH3CH2COOH (D) CH3 CHCOOH

C N
Soln:

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 39 GENERAL ORGANIC CHEMISTRYI - I
Q-11 Find the strongest acid among the following compounds.
(A) HOOC – (CH2)2 – COOH (B) H3 N  – (CH2)2 – COOH

(C) F – (CH2)2 – COOH (D) CH3 – (CH2)2 – COOH

Soln:

Q-12 HC  C – CH 2 – COOH CH 2  CHCH 2 COOH CH 3 CH 2 COOH

(I) (II) (III)
Order of Ka will be :
(A) I > II > III (B) II > I > III (C) III > II > I (D) I > III > II
n
Sol :

O O O
C C – OH C – OH
OH
Q-13
O2 N CH 3O
I II III

Order of Ka will be :
(A) I > II > III (B) II > I > III (C) I > III > II (D) III > I > II

Soln:

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CHEMISTRY 40
Q-14 Amongest the following compounds the strongest acid is :
COOH SO3H OH
CH2OH
(A) (B) (C) (D)

Soln:

Q-15 Select the order of basic strength.

(I) R4 OH¯ (II) R3N (III) R2NH (IV) RNH2 (if R = Me)
N
(A) (I)>(III)>(IV)>(II) (B) (IV)>(III)>(I)>(II)

(C) (II)>(IV)>(III)>(I) (D) (II)>(IV)>(I)>(III)

Soln:

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 41 GENERAL ORGANIC CHEMISTRYI - I
Q-16 Order of basic strength in the following compounds.
.. .. ..
NH 2 NH 2 NH 2
(p)

CH 3 NO 2
I II III
(A) II > I > III (B) I > II > III (C) III > II > I (D) II > III > I
O
NH 2 NH 2
C – CH 3

(q)
Cl CH 3
NH 2
I III
II
(A) I > II > III (B) III > I > II (C) III > II > I (D) II > I > III

(r) NH 2 NH 2
NH

(I) (II) (III)

(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III

Soln:

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CHEMISTRY 42
Q-17 Select the decreasing order of relative basic strengths of following species :
(p) OH¯, NH2¯, H – C  C¯, CH3 – CH2¯
(A) CH3 – CH2¯ > NH2¯ > H – C  C¯ > OH¯ (B) H – C  C¯ > CH3– CH2¯ > NH2¯ > OH¯
(C) OH¯ > NH2¯ > H – C  C¯ > CH3 – CH2¯ (D) NH2¯ > H – C  C¯ > OH¯ > CH3 – CH2¯
(q) (I) (CH3)3 C- (II) (CH3)2 N- (III) (CH3)3 CO- (IV) CH3O -
(A) (I) > (II) > (III) > (IV)
(B) (III) > (IV) > (II) > (I)
(C) (I) > (II) > (IV) > (III)
(D) (II) > (IV) > (III) > (I)

(r) (I) (II) (III) (IV) ••

•• N
N N
•• |
| • NH
• 2 H
H

(A) (IV) > (I) > (II) > (III)

(B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III)
(D) (II) > (I) > (III) > (IV)

(s) (I) CH3ONa (II) CH3NHNa (III) CH3COONa (IV) CH3Na

(A) (IV) > (II) > (I) > (III)
(B) (III) > (I) > (IV) > (II)
(C) (IV) > (II) > (III) > (I)
(D) (II) > (I) > (III) > (IV)

NH NH2 NH NH2 NH NH2 NH NH2

C C C C
| | | |
(t) (I) (II) (III) (IV)
| | |
NH2 NO2 Cl

(A) (II) > (IV) > (I) > (III) (B) (III) > (I) > (IV) > (II)

(C) (III) > (IV) > (I) > (II) (D) (II) > (I) > (IV) > (III)

Soln:

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 43 GENERAL ORGANIC CHEMISTRYI - I

Q-18 The basic strength order of following anion :

– – – – – –
(A) CH3–CH2 > NH2 > CH2=CH > CHC > HO > F
– – – – – –
(B) NH2 > CH3–CH2 > CH2=CH > CHC > F > HO
– – – – – –
(C) CH3–CH2 > CH2=CH > NH2 > CHC > HO > F
– – – – – –
(D) F > HO > CHC > CH2=CH > NH2 > CH3–CH2

Soln:

Q-19 Write the order of basic strength.

O

N N
N N
| |
H H
H
(I) Piperidine (II) Pyridine (III) Morpholine (IV) Pyrrole

(A) (IV) > (I) > (III) > (IV) (B) (III) > (I) > (IV) > (II)
(C) (II) > (I) > (III) > (IV) (D) (I) > (III) > (II) > (IV)
Soln:

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CHEMISTRY 44
Q-20 Increasing order (least basic first) of basic strength is shown by the set

(A) ClNH2, NH3, CH3NH2 (B) ClNH2, CH3NH2, NH3

(C) NH3, ClNH2, CH3NH2 (D) CH3NH2, ClNH2, NH3

Soln:

Q-21 The decreasing order of acid strength indicated by the following sequence of reaction is :-

NaNH2   C2H2 H2O

–C–H –C–Na HC CNa+ Ph3CH HC CH + NaOH

(A) NH3 > Ph3CH > C2H2 > H2O (B) H2O > HC  CH > Ph3CH > NH3

(C) HC  CH > H2O > Ph3CH > NH3 (D) Ph3CH > HC  CH > H2O > NH3
Soln:

Q-22 Among the following, the strongest base is :-

(A) C6H5NH2 (B) p–NO2–C6H4NH2

(C) m–NO2–C6H4NH2 (D) C6H5CH2NH2

Soln:

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 45 GENERAL ORGANIC CHEMISTRYI - I
Q-23 Which of the following compounds is the strongest base -

(A) NH2 (B) NH2 (C) CH3 NH2 (D) NHCOCH3

Soln:

Q-24 The correct order of decreasing basic strength is :

NH2

N N N
H H
I II III IV

(A) I > II > III > IV (B) II > III > I > IV (C) II > IV > I > III (D) II > III > IV > I
Soln:

Q-25 Which one of the following is the strongest base in aqueous medium :-

(A) (C2H5)3N (B) C2H5NH2 (C) NH3 (D) (C2H5)2NH

Soln:

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CHEMISTRY 46
Q-26 The correct order of acid strength of the following compound is -

(I) CH3–C–CH3 (II) CH3–C–C–CH3 (III) CH3–C–CH2–C–CH3

O OO O O

(A) III > II > I (B) III > I > II (C) II > I > III (D) I > II > III

Soln:

Q-27 Which of the following shows the correct order of decreasing basicity in aqueous medium -

(A) (CH3)3 N > (CH3)2NH > CH3NH2 > NH3

(B) (CH3)2 NH > (CH3)3N > CH3NH2 > NH3

(C) (CH3)2 NH > CH3NH2 > (CH3)3N > NH3

(D) (CH3)2 NH > CH3NH2 > NH3 > (CH3)3N

Soln:

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 47 GENERAL ORGANIC CHEMISTRYI - I
Q-28 For the compounds

N N N
H H
I II III

the order of basicity is -

(A) III > II > I (B) II > III > I (C) I > II > III (D) II > I > III

Soln:

Q-29 Which of the following shows the correct order of decreasing acidity-

(A) PhCO2H > PhSO3H > PhCH2OH > PhOH

(B) PhSO3H > PhOH > PhCO2H > PhCH2OH

(C) PhCO2H > PhOH > PhCH2OH > PhSO3H

(D) PhSO3H > PhCO2H > PhOH > PhCH2OH

Soln:

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CHEMISTRY 48
Q-30 Give the correct order of increasing acidity of the following compounds-

OH OH COOH CCH

I II III IV

(A) II < I < III < IV (B) IV < II < I < III

(C) I < II < IV < III (D) IV < I < II < III
Soln:

Q-31 Which of the following is the most acidic

(A) CH2 = CH2 (B) HC  CH

(C) CH2=CHCH2CH=CH2 (D)

Soln:

Q-32 Which of the following substituents will increase the acidity of phenol -

(A) –NO2 (B) –CN (C) –CHO (D) – CH3

Soln:

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Q-33 NH, N–H, N

O
(x) (y) (z)

The correct order of decreasing basic strengths of x, y and z is :

(A) x > y > z (B) x > z > y (C) y > x > z (D) y > z > x
Soln:

Q-34 Set the following in increasing order of their p K a values:

O O

(x) CH3—S—O—H (y) CH3—C—O—H (z) CH3—OH

O
(A) y>x>z (B) x < y < z (C) y > z > x (D) x < z < y

Soln:

Q-35 Rank the following alkenes in order of decreasing heats of hydrogenation (largest first):

(I) (II) (III) (IV)

(A) II > III > IV > I (B) II > IV > III > I

(C) I > III > IV > II (D) I > IV > III > II
Soln:

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CHEMISTRY 50
Q-36 Which nitorgen in LSD (Lysergic acid diethylamide) is more basic :

O
I III
H–N –C–N(C2H5)2
II
N
CH3

(A) I (B) II (C) III (D) all are equally basic

Soln:

Q-37 Which of the following substituted carboxylic acids has the highest Ka value :

(A) CH3—CH2 —CH— COOH (B) CH3 —CH— CH2—COOH

Cl Cl

(C) CH2— CH2—CH2—COOH (D) CH3 —CH— CH2—COOH

Cl Br

Soln:

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 51 GENERAL ORGANIC CHEMISTRYI - I

Q-38. The acid strength of substituted carboxylic acids is known to be dependent on the nature and
position of the substituent. In the following examples, an attempt has been made to arrange the
acids in order of acid strength, the strongest first. One of the series is incorrect-which one :

(A) CH3.CH2CH(Cl).COOH > CH3 .CH(Cl).CH2COOH > CH3.CH2.CH2.COOH

(B) NO2.CH2.COOH > HOCH2. COOH > CH3.COOH

(C) Cl3C.COOH > BrCH2.COOH > FCH2.COOH

(D) CH3.COOH > CH3.CH2.COOH > (CH3)3C.COOH

Soln:

Q-39 Select the correct option :

(A) carbonic acid is weaker acid than acetic acid

(B) the boiling points of acids are higher than corresponding alcohols

(C) chloroacetic acid is stronger acid than acetic acid

(D) phenol is more acidic than ethanol

Soln:

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CHEMISTRY 52
Q-40 Which statement is ture :
– –
(A) NH2
is stronger base than OH

(B) NH2–OH is less basic than NH3

(C) CH3–NH2 is weaker base than N(CH3)3 in (aq) medium

NH2 CH2–NH2

(D) is weaker base than

Soln:

Q-41 Which is less acidic than phenol :

OH OH

—CH3 —NH2
(A) (B) CH3–OH (C) (D) H2O

Soln:

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ANSWERS
ABHYAAS - I

CH = CH2
COOH
CH3 COONa
Q-1 (P) COOH
(Q) (R) (S)
OH NaO
C CH

Q-2 Decreasing order of dipolemoment for given compounds

(x) : I > IV > III > II ; (y) : I > III > II > IV
Q-3 (B) Q-4 (D) Q-5 (C) Q-6 (D) Q-7 (A) Q-8 (B) Q-9 (D)
Q-10 (C) Q-11 (D) Q-12 (C) Q-13 (A) Q-14 (A) Q-15 (C)

ABHYAAS - II

Q-1 O O O O O

Phenol doesnot have low energy forms such as the three at the right, because the oxygen atom
would have a partial positive charge.

Q-2 H3C CH2 H3C H3C CH2

OH OH OH

Q-3 a, d, f, g, i, j

Q-5 (B) Q-6 (B) Q-7 (D) Q-8 (B) Q-9 (C) Q-10 (B) Q-11 (C)
Q-12 (D) Q-13 (B)

Q-14    

In resonting structure of phenoxide negative charge is present on C-atom (which is less electronegative)
while in benzoate ion, negative charge is present on more electronegative O atom. Hence in resonating
structure, if negative charge is present on more electronegative atoms it is more stable in comparison to
that resonating structure which have negative charge on less electronegative atoms.

Q-15 (A) Q-16 (A) Q-17 (C) Q-18 (C) Q-19 (B)

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ABHYAAS - III

Q-1 (a) 3, (b) 5, (c) 9, (d) 5 Q-2 I > III > II > IV

Q-3 (B) Q-4 (D) Q-5 (A) Q-6 (D)

Q-7 CH2=C=CH2 (Allene)

sp2 sp sp2

Q-8 (C) Q-9 (B)

ABHYAAS - IV

Q-1 (B) is more stable carbocation due to extented conjugation

Q-2 (p) (A) > (D) > (C) > (B)

(q) (C) > (B) > (D) > (A)

(r) (D) > (C) > (B) > (A)

Q-3 (D) Q-4 (C) Q-5 (C) Q-6 (C) Q-7 (A) Q-8 (A) Q-9 (B)

Q-10 (A) Q-11 (C) Q-12 (D) Q-13 (C) Q-14 (7) Q-15 (B) Q-16 (C)

Q-17 (C) Q-18 (C) Q-19 (C) Q-20 (A) Q-21 (B) Q-22 (C)

ABHYAAS - V
Q-1 (a) I – minor II – major
(b) I – minor II – major
(c) I – minor II – major
(d) I – minor II – major

   
Q-2 (D) Q-3 (B) Q-4 CH3 < NH2 < OH < F Q-5 (C) Q-6 (A)

Q-7 (D) Q-8 (A)

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ABHYAAS - VI

Q-1 In both series, charge rests on C. In (a) –I effect of Cl destabilizes cation. The order is

   
C H 3  C H 2Cl  C HCl 2  C Cl 3 .

In (b) –I effect of Cl stabilizes anion. The order is

CCl 3–  CHCl –2  CH 2Cl –  CH 3–

Electron with drawing group increases +ve charge of C in a cation; stability decreases. This group
decreases the –ve charge of C by drawing electrons away; stabilized.

Charge concentration is destabilizing.

Charge dispersal is stabilizing.

Q-2 (C) Q-3 (p) (B) (q) (C) Q-4 (C) Q-5 (AC)

ABHYAAS - VII

Q-1 I > II (–M effect)

Q-2 (p) A > B > C > D (Order of Ka) (q) A > B > C ~_ D (Order of Ka)

(r) (A) > (D) > (C) > (B) (s) (A) > (B) > (D) > (C)

(t) (A) > (B) > (C) > (D)

Q-3 Due to better solvation in polar protic solvent.

Q-4 (P) I > II > III ; (Q) I > II > III ; (R) I > II > III

Q-5 ERG increases the basic strength because they tend to stabilise protonated aniline, on the other hand,
EWG decrease the basic strength they tend to destabilise the protonated aniline.

(G stabilises the cation) (G' destabilises the cation)

Q-6 I > II > III
Q-7 (p) (A) > (B) > (D) > (C) (q) (D) > (B) > (A) > (C) (r) (D) > (A) > (C) > (B)
Q-8 (D) Q-9 (A) Q-10 (A) Q-11 (B) Q-12 (A) Q-13 (C) Q-14 (B)
Q-15 (A) Q-16 (p) (A), (q) (B), (r) (A) Q-17 (p) (A), (q) (A), (r) (D), (s)(A), (t) (D)
Q-18 (C) Q-19 (D) Q-20 (A) Q-21 (B) Q-22 (D) Q-23 (B) Q-24 (D)
Q-25 (D) Q-26 (A) Q-27 (C) Q-28 (D) Q-29 (D) Q-30 (B) Q-31 (D)
Q-32 (ABC) Q-33 (B) Q-34 (B) Q-35 (D) Q-36 (B) Q-37 (A)
Q-38 (C) Q-39 (ABCD) Q-40 (AD) Q-41 (ABD)

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