Reaction Intermediate (Free Radical and Carbocation) Question Bank PDF

ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
IIT-JEE ChEmistry by N.J. sir
ORGANIC chemistry
IR
REACTION
.S
INTERMEDIATES
Part – 1 (Question Bank)
.J
(Free Radical &

N
Carbocation)
1
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ETOOS Education Pvt. Ltd.
Plot No. 68, Near Union Bank of India, Rajeev Gandhi Nagar, Kota, Rajasthan – 324005
Mob. No. : 9214233360
IIT-JEE ChEmistry by N.J. sir ORGANIC chemistry
DPP NO- 1 Time: 15 minutes
Q.1 Matrix
Reactions Number of dimerization product
(excluding stereoisomers)
(A) Na
CH3 — CH2 — Cl   (P) 1
Dry ether
Cl
(B) Na
  (Q) 3
Dry ether
IR
14
(C) Na
H2C = CH — CH2 — Cl   (R) 6
Dry ether
14
(D) * Na
Cl  *  CH ) (S)
 + CH3 — Cl (H2C None
Dry ether 2
Q.2 Identify major products.

CH2Br
.S
AlHg
(1) + 4 Na  (2)  
C2H5OH
Br
O
I Cl
I
.J
(3) I+ Cu
 (4) Na
 
120260C Dry ether
I
Cl
Br
N
Na  14 Na 
(5)  (6) 
DE D.E
Br
Na  Cl Na
(7)  (8)  
DE Dry ether
Br
(9) Na
 
Dry ether
Br
2
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Mob. No. : 9214233360
DPP No.2 Time: 10 minutes
Free Radicals:–
Wurtz Reaction:–
R — X  Na  R— R
ether
Mechanism:– (Free radical Mechanism)

(1) Na Na+ + e–
 :
(2) R — X + e–  R + X
 
(3) R + R R — R
(Ionic Mechanism)
Na Na+ + e–
IR
(1)
:
(2) R — X + 2e–  R + X

 
:
(3) R + R — X R — R + X
Q.1 CH3 — Cl  Na  _ _ _ _ _ _ _

ether
.S
Q.2 Na  _ _ _ _ _ _ _
Et — Cl 
ether
Q.3 Na  _ _ _ _ _ _ _
CH3 — Cl + Et — Cl 
ether
Q.4 Na  _ _ _ _ _ _ _
(Ph)3 CI 
ether
Q.5 Na  _ _ _ _ _ _ _
I 
ether
.J
Na/ ether  _ _ _ _ _ _ _
Q.6 Cl Br 
Br
Na/ ether  _ _ _ _ _ _ _
N
Q.7 Br 
Q.8 Na/ ether  _ _ _ _ _ _ _ _ _


Cl Cl
Cl
Q.9 Na/ ether  _ _ _ _ _ _ _

Br
Q.10 Na/ ether  _ _ _ _ _ _ _
Cl Cl 
Cl Na/ ether  _ _ _ _ _ _ _
Q.11 Cl 
Q.12 Na  _ _ _ _ _ _ _ (fitting Reaction)
Ph — Cl 
THF
3
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Mob. No. : 9214233360
Q.13 Na  _ _ _ _ _ _ _ (Wurtz fitting)
Cl + Cl — CH3 
THF
Cl
Q.14 Na  _ _ _ _ _ _ _

ether
Cl
Zn  _ _ _ _ _ _ _
Q.15 CH2—CH2 
Br Br
Cl
Ag/Powder
Q.16 H—C—Cl   _______
Cl
Q.17 Na/ ether  _ _ _ _ _ _ _
CH2—CH=CH—CH2 
Br Br
I
IR
Q.18 Na/ ether  _ _ _ _ _ _ _

Br
.S
.J
N
4
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Mob. No. : 9214233360
DPP No.3 Time: 15 minutes
Kolbe Electrolysis:–
O
NaOH R—R + CO2 + H 2
R — C —OH 
electrolysis
Anode Cathode
Mechanism:–
O O H
 —
(1) R — C —O—H + 

 R
OH  — C —O + O
H
Anode:–
IR
O O
 –
(1) R — C —O—  R — C — O + e
O
 
(2) R — C — O  R + CO2 
 
(2) R + R R — R
.S
Cathode:–
(1) 2H2O + 2e— 2O H + H2
electrolysis
Q.1 CH3 COOK  _ _ _ _ _ _ _
Q.2 NaOH
Et — COOH  _______
electrolysis
.J
Q.3 NaOH
COOH  _______
electrolysis
HOOC
COOH
Q.4 NaOH
 _______
electrolysis
N
COOH
Q.5 KOH _______
COOH 
electrolysis
HOOC
electrolysis
Q.6 NaOOC COONa  _ _ _ _ _ _ _
electrolysis
Q.7 COONa  _ _ _ _ _ _ _
NaOOC
electrolysis
Q.8 KO3S SO3K  _ _ _ _ _ _ _ _ _
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Mob. No. : 9214233360
COOH NaOH
Q.9  _______
electrolysis
SO3H
COOH
Q.10 NaOH
 _______
electrolysis
COOH
SO3K
electrolysis
Q.11  _ _ _ _ _ _ _
SO3K
IR
electrolysis
Q.12 KO3S  _ _ _ _ _ _ _
C C
SO3K
.S
.J
N
6
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Mob. No. : 9214233360
Q.1 Identify the major product:-
CH2 — I
(1) Na
+  
Dry ether
Br Br
(2) + Na 

DE
IR
Br Br
CH2 CH2
(3) Na
 
Dry ether
Br
.S
(4) Na
 Se  (B)
 (A) 
Dry ether
Br
Br
Na
.J
(5) 
D.E.
Br
Br
(6) Na
  Naphthacene
Dry ether
N
Br
CH2 — Br
(7) Na
  (A) + (B); (A) & (B) are isomer.
Dry ether
CH2 — Br
Br
* Na Na
(8) H2C = CH — CH2 — Cl  A + B + C (9)  
Dry ether Dry ether
Cl
7
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Mob. No. : 9214233360
Cl
Cl
(10) Na
  (11) Na
 
Dry ether Dry ether
Cl Br
Cl
(12) CH3 — CH2 — Cl + Na
  (13) Na
 
Dry ether Dry ether
2. Which of following is correct matching of energy profile diagram?
 
(1) CH3  Cl  CH3 — Cl E
IR
rxn - coordinate
(2) hv  2Cl
Cl — Cl  E
rxn - coordinate
.S
(3) CH3  + CH3   CH3 — CH3 E
rxn - coordinate
(4)

Cl  + H — CH3  H — Cl + CH3 E
.J
rxn - coordinate
 KJ   KJ 
Bond energy  H  Cl  432   CH3  H  440 
 mole   mole 
3. When pentane is heated to a very high temperatue, radical reactions take palce that produce (among
N
other products) methane, ethane, propane, and butane. This type of change is called thermal cracking.
Among the reactions that take place are the following:-
(1) CH3CH2CH2CH2CH3  CH3  + CH3CH2CH2CH2 
(2) CH3CH2CH2CH2CH3  CH3CH2  + CH3CH2CH2 
(3) CH3  + CH3   CH3CH3
(4) CH3  + CH3CH2CH2CH2CH3  CH4 + CH3CH2CH2CH2CH2 
(5) CH3  + CH3CH2   CH3CH2CH3
(6) CH3CH2  + CH3CH2   CH3CH2CH2CH3
(a) For which of these reactions would you expect Eact to equal zero?
(b) To be greter than zero?
(c) To equal H°?
8
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Mob. No. : 9214233360
1. Compound Number of monochloroproduct Number of monocloroproduct
(excluding stereoisomer)
1.
2.
3.
4.
5.
6.
IR
7.
8.
9.
.S
CH2
2.
1. Compound Number of Dichloroproduct Optically active product
(including stereoisomer)
1. 1-chlorobutane
.J
2. R-2-chlorobutane
3. 3-chloropentane
4. R-2-chloropentane
N
5. S-2-chlorobutane
6. R & S-2-chloropentane
7. R & S-2-chloro butane
9
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Mob. No. : 9214233360
1. Which of following carbocation will undergo rearrangement?
+ +
CH2 CH2
(a) (b) (c) (d)

+
+
+
+
+ +
(e) (f) (g) (h)
O
IR
Ph
+ +
(i) CH2 — O — CH2 — CH2 — CH2 (j)
+
.SCH2
+ +
+
CH3 (n) CH
(k) (l) (m) 2 — CH2 — CH2
CH3 — CH2 — O
+
.J
Ph +
+ CH
(o) (p) CH2 — C = O (q)
+ 
N
(r) CH3CH2CH2 (s) (CH3)2 CH CHCH3
 +
(t) (CH3)3 C CHCH3 (u) (CH3CH2)3CCH2
CH2—OH
2. H  (A)


(A) an heating isomerizes to (B). What is the structure of (B).

CH3 OH
(A) (B) (C) (D)
10
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Mob. No. : 9214233360
Ph — CH — Ph
CH2 — CH2 — OH
3. H 

 (A) , Major product (A) is
(major)
Ph — C — Ph Ph — CH — Ph
CH2 — CH3 CH — CH3
(A) (B)
Ph
Ph — CH — Ph Ph — C — OH
IR
CH — CH2 CH2 — CH3
(C) (D)
OH
.S
4. Reaction-1 H 

 (A)
(major)
Reaction-2 H 

 (A)
OH (major)
.J
Reaction-3 H 

OH  (A)
(major)
Sum of -hydrogen (A + B + C) is.

N
5. (A) H  (x)
 (B) H  (y)

 
OH OH
OH
(C) H  (z)
 (D) H  (p)

 
OH
Total number of products obtained in above reactions including minor products is (include
stereoisomer)
x y z p
11
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Mob. No. : 9214233360
6. In which of following reaction rearrangement take place with change is carbon skeleton.
CH3
+
(A) CH3 — C — CH 2 (B) CH3 — CH2 CH2 
CH3
+
(C) CH3 — CH — CH2 — CH2 (D) CH3 — CH  — CH3
CH3
7. Sum of -hydrogen in major product of the reaction.

OH
Reaction-1 H  (A)


IR
OH
Reaction-2 H  (B)


.S OH
Reaction-3 H  (C)


OH
H  (D)
.J
Reaction-4 

Sum of -hydrogen is A+B+C+D=
8. In which of following reaction resonance stabilized product will form.

N
CH2—OH OH
(A) H


(B) H 
 

CH3
(C) OH H 
 (D) All

12
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Mob. No. : 9214233360
DPP NO-7 Time: 15 minutes
Q.1
(a) CH3—CH2—CH2  __________
(b)  __________
(c)  __________
CH3
IR
(d) CH3—CH2—CH2—C—CH2  _ _ _ _ _ _ _ _ _
CH3
(e)  ________

.S
(f)  _ _ _ _ _ _ _ _ _
(g) Ph—CH2—CH2  _______

.J
CH3
(h) CH3—CH—CH2—CH2  _______
Ph Me
N
(i) Ph—C— CH—CH2—CH2  _______
D
Ph
(j) CH3–O C—CH2—CH2—CH2  _ _ _ _ _ _ _ _ _
Ph
(k)  _________
13
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Mob. No. : 9214233360
(l) CH3—CH—CH2—OH  _________
OH
(m)   _________
CH3 Me
(n) CH3—C— C—et  _________
OH
CH3
IR
:
(o) CH3— C — C = O:  _________
H
CH—OH
2
(p)
.S  _______ _
CH2
(q)  _________
.J
CH2
(r)  _________
(s)  ________

N
(t)  _________
(u)  _______ _
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Mob. No. : 9214233360
(v)  _________
OH
(w)  _________
OH
(x)  ________
`
IR
.S
.J
N
15
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Mob. No. : 9214233360
Dehydration of Alcohol
Conc.H2SO4
Q.1 CH3 — CH2 — CH2 — OH   CH3 — CH = CH2
170C
Mechanism:–
H

:
(1) CH3 — CH2 — CH2 — O +

+ H 
 CH3 — CH2 — CH2 —
—H O
H
rds
H

CH3 — CH — CH3 CH3 — CH2 — CH2  +  :O:
IR
H
H

(2) CH3 — CH — CH3 + :O: CH3 — CH = CH2 + H3O+
H
Energy profile diagram:—
.S
E
Reaction
.J
Q.1 H /  _ _ _ _ _ _ _

Q.2 H /   _ _ _ _ _ _ _
OH  
OH
Q.3 H /   _ _ _ _ _ _ _ Q.4 H / 
_ _ _ _ _ _ _
 OH 
OH
N
Conc.H2SO4 Conc.H2SO4
Q.5 
 _ _ _ _ _ _ _ Q.6 
 _ _ _ _ _ _ _
OH OH
OH
Q.7 H  _ _ _ _ _ _ _


OH
Conc.H2SO4
Q.8 
 _ _ _ _ _ _ _ _ _
OH
Q.9 H /   _ _ _ _ _ _ _

16
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Mob. No. : 9214233360
OH
Q.10 H /   _ _ _ _ _ _ _

Q.11 H /  _ _ _ _ _ _ _
OH 

Electrophilic addition:–
ENu 

C=C C—C
E Nu
Mechanism:–
C=C + E  —C — C—
E 
IR
:
Nu
Nu
—C — C—
E
.S
Q.1 Compare rate of electrophilic addition on alkenes:–
(a)
(i) (ii) (iii) (iv)
CH = CH2 CH = CH2 CH = CH2 CH = CH2 CH = CH2

(b)
.J
NO2 CN O – Me NH2
(i) (ii) (iii) (iv) (v)
N
COOH
(c)
(i) (ii) (iii) (iv) (v)
(d) Ph — CH = CH2 PH — CH = CH — Ph
(i) (ii)
Q.1 HI  _ _ _ _ _ _ _ _ _ _
CH2 = CH2 
Q.2 KBr
CH2 = CH2  __________
Q.3 HI
 __________
KBr
17
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Mob. No. : 9214233360
Q.4 HI __________
C = CH2 
KBr
Q.5 HI  _ _ _ _ _ _ _ _ _ _

KF
Q.6 HI  _ _ _ _ _ _ _ _ _ _

Q.7 HCl  _ _ _ _ _ _ _ _ _ _

O
Q.8 HI  _ _ _ _ _ _ _ _ _ _

IR
Q.9 HI  _ _ _ _ _ _ _ _ _ _
(Ph)2 CH—CH—CH=CH2 
Me
Q.10 HBr
C = CH—Ph  _ _ _ _ _ _ _ _ _ _
.S
Q.11 HCl  _ _ _ _ _ _ _ _ _ _

Q.12 HBr
 __________
Q.13 HCl  _ _ _ _ _ _ _ _ _ _
CH2 = CH — Cl 
.J
HCl(2eq.)
Q.14 CH  CH   __________
HCl(2eq.)
Q.15 CH3 — C  CH   __________
N
Q.16 HCl  _ _ _ _ _ _ _ _ _ _

dil.H2SO4
Q.17   __________
H /H2O
Q.18   __________
Q.19 H /R–OH  _ _ _ _ _ _ _ _ _ _

H /H2O
Q.20   __________
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Mob. No. : 9214233360
Me
HCl  _ _ _ _ _ _ _ _ _ _
Q.21 H D 
CH = CH2
D /D2O
Q.22   __________
O
H
+ H
Q.23 __________
Q.24 HBr
 __________
Q.25 HCl  _ _ _ _ _ _ _ _ _ _
CH  C — CH2 — CH = CH2 
IR
Q.26 HCl  _ _ _ _ _ _ _ _ _ _
CH  C — CH = CH2 
Q.27 H
HO — CH2 — CH2 — CH2 — CH = CH2  __________
MeOH
OH
Q.28 H /MeOH  _ _ _ _ _ _ _ _ _ _

CH2= CH—CH—CH=CH2 
.S
Q.29 H  _ _ _ _ _ _ _ _ _ _

O
H
.J
N
19
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Mob. No. : 9214233360
Q.1 Compare rate of dehydration (acid-catalyzed)
OH OH
OH OH OH OH
(a) (b) (c)
OH
OH
(d) OH (e)
OH
Q.2 Predict the major product of acied-catalyzed dehydration of alcohols

(A) 2-pentanol (B) 1-methyl cyclopentanol
IR
(C) 2-methyl cyclohexanol (D) 2, 2-dimethyl-1-propanol
Q.3 Identify-Product
CH3 CH3
H2 SO4 H SO
(a)  
(b) CH3—CH2—C — CH—CH3 
2

4
OH OH
OH
— CH2 — OH
.S H3PO4 H PO
(c) 

(d) — CH — CH 2 — CH3 
3

4
OH
CH3
H H 
(e) 

(f) CH3—CH2—CH — C —CH3 

OH CH3
OH
.J
(g) OH 
H
(h) H


A+B
 
CH3
H H
H  H 
(i) 
A+B (j) 

A+B
CH3 OH
N
OH
OH
OH
KHSO4 H2 SO4
(k) 
170 C
 (l) 
OH OH
H2 SO4 H2 SO4
(m) 
(n) 
CH3
CD3
OH
OH
 
H H
(o) 

(p) 

20
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Mob. No. : 9214233360
OH
CH3
D D Cl
(q) D D 
H
(r) H
 (s) H3PO4

  
OH OH
Q.4 Write – Mechanism

(a) OH 
H


H2 SO4
(b) 
OH
 18
(c) CH2 — CH — CH2 — CH2 — CH2 
H
 + H2 O 

O
IR
CH3
OH OH
18
Q.5 Predict Major Product

CH2
HCl HCl
(a) 
 (b)  
.S
HCl HCl
(c)   (d) 2-methyl propene  

Hl
(e) 1-methyl cyclohexene  
.J
N
21
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Mob. No. : 9214233360
Q.1 Identify major products:
CH3
HgSO4 HgSO4
(a) CH3 — C — C CH 
H2 SO4
 (b) CH3 — C  CH 
H2 SO4

CH3
HgSO4
(c) CH3 CC 
H2 SO4

C CH C CH

HgSO4 H3 O
(d) 
H2 SO4
 (e)  
IR
C CH

HgSO4 H3 O
(f) CH3 — C  CH 
 H2 SO4
(g)  
 
H3 O H3 O
(h) l-phenyl cyclohexene  (i) l-methyl cyclopetene 
.S  
HBr HBr
(j)   (k) Ph — CH2 — CH = CH2 
CCl4

Q.2 Find total product in following reaction ? (including stereoisomer)


H HBr
(a) OH 

 (x) products 
CCl4
 (y) (products) (Markonikoff products)
.J
Br2
(z) (products)
CCl4
OH
 OH 
H HBr H
(b) 

 (A) 
CCl4
 (B) (c) 


N
Br2
(C)
CCl4
H H H3 O 
HBr
(d) C=C   (e) 
CCl4

Ph Ph
(f) D–Cl
(x)
D3 O+
(y)
22
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Mob. No. : 9214233360
Q.3 What will be major – product obtained from addition of HBr to each of the following compounds.
CH3 CH2
(a) CH3 — CH2 — CH = CH2 (b) (c)
CH3 CH3
(d) CH3 — CH = C — CH3 (e) H2C = C — CH2 — CH3
(f) CH3 — CH = CH — CH3 (g) HO CH = CH2
(h) CH3 — CH — CH2 — CH = CH2 (i)

CH3
CH3
IR
(j) (k)
.S
.J
N
23
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Mob. No. : 9214233360
Q.1 How will prepare following compound using alkene as the starting material ?
OH Br
(a) (b) (c)
OH
CH3 Br
(d) (e) CH3 — O — C — CH 3 (f)
Br CH3
OCH3
(g) OH (i)
IR
Q.2 Identify reactant in following reaction
Br2
(a) (A) CCl4
 meso – 2, 3 – dibromobutane
Br
Br2
(b) (B)   + Mirror Image
.S CCl4
Br
Br
HBr
(c) (C) 
CCl4

HBr Br
(d) (D)  
.J
CCl4
CH3
HBr
(e) (E) 
 CH3 — C — CH2 — Br
CCl4
CH3
N
O
H3 O
(f) (F) 
HBr
(g) (G) 
CCl4
 racemic mixture of 2, 3 – dibromobutane.
Q.3 Write – Mechanism
OH

(a) H


 H3 O
(b) Ph — CH2 — CH2 — OH   Ph — CH — CH3
24
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Mob. No. : 9214233360
O
CH3—CH—CH—CH3 H
Q.1   CH3—CH2—C—CH3

OH OH
Mechanism:–
+ +
(1) CH3—CH—CH—CH 3 +H  H2 O + CH 3—CH—CH—CH 3
:
:O–H O–H O–H
IR
+
s CH3 — CH 2—C—CH 3  CH3 — CH 2—C—CH 3
:
O—H O—H
+
CH3 CH3
Q.1 H 
Et — C — C —Et 
.S 
OH OH
Ph
Q.2 H 
Ph— C — CH 2 

OH OH
OH OH
H H
.J
Q.3 H 


OH OH
CH3 CH3
N
Q.4 H 


OH OH
Q.5 H 

CHO
3 C—C— 
H H
OH OH
Q.6 H 


25
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Mob. No. : 9214233360
OH OH
Q.7 H 


Diazotization of primary amine:–

 NaNO2
R — NH2   R — N  N :  
 R  N2
HCl
Mechanism:–
(1) NaNO2 + HCl  H—O—N=O + NaCl
:
(2) H — O — N = O + H H2O + N=O
+
H H H
:
:
:
(3) R—N: + N = O  R—N — N = O  R—N—N = O—H
:
IR
H H
H
: :
R—N= N—O—H
.S
 H H
:
:
:
N2  R  R — N  N :  R—N =N + O  R—N = N—O: 
H H
Demjanov Reaction:–
OH NH2 O
.J
NaNO2
CH3 — CH—CH—CH3 
HCl
 CH3 — C—CH2—CH3
Mechanism:–
OH NH2 OH
NaNO
N
(1) 2
CH3 — CH—CH—CH3 
HCl CH3 — CH—CH—CH3 + N2
O OH
H + CH3 — C—CH2—CH3  CH3 — C—CH2—CH3 
OH NH2
NaNO
2 _ _ _ _ _ _ _ _ _ _
Q.1 CH — CH — —OCH3 
HCl
NH2
NaNO2
Q.2   __________
HCl
OH
26
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Mob. No. : 9214233360
NH2 OH
NaNO2
Q.3   __________
HCl
OH NH2
NaNO2
Q.4 CH3 — CH —CH—   __________
HCl
SbCl5
Q.5   __________

Cl O—H
OH
Br
IR
AlBr3
Q.6   __________

AgI
Q.7   __________

I
.S
O—H
OH
aq. AgNO3
Q.8   __________
I
.J
N
27
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Mob. No. : 9214233360
Non Classical Carbocation:–
Nu
E—Nu  —C — C—

C=C
E
Mechanism:–
:
(1) C = C  —C — C— + Nu
E
E
Nu
IR
Nu
—C — C—
E
Br2
Q.1
.S
CH2 = CH2   _______
Q.2 CH2 = CH2

Br2 _______
O
H H
Br2
Q.3  _ _ _ _ _ _ _
CCl4
.J
Br2
Q.4  _ _ _ _ _ _ _
CCl4
Q.5 ICl  _ _ _ _ _ _ _
CH3 — CH = CH2 
Q.6 HOCl  _ _ _ _ _ _ _
CH3 — CH = CH2 
N
Cl2
Q.7  _ _ _ _ _ _ _
CCl4
Br2
Q.8  _ _ _ _ _ _ _ _ _
CCl4
Br2 /H2O
Q.9   _______
Br2
Q.10  _______
H2O
Br2 /CCl4
Q.11  _______
(1eq.)
28
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Mob. No. : 9214233360
H
N Br2 (CCl4 )
Q.12   _______
(1eq.)
Q.13 HCl  _ _ _ _ _ _
CH3 — CH = CH2 
CH3Cl / AlCl3
CH3Cl
H H–O CH3
Q.14 ______
Q.15 HCl  _ _ _ _ _ _
CH3 O— 
IR
Diel’s Alder Reaction:–
+ ||  
.S
COOH
Q.1 + 
COOH
COOH

.J
Q.2 +
HOOC
Q.3 + 
NO2
N
Q.4 + 
Q.5 + 
Q.6 + 
29
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Mob. No. : 9214233360
Q.7 + 
Q.8 + 
IR
Q.9 .S + 
Q.10 + O 
O
.J
Q.11 + 
N
Q.12 O + 
30
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Mob. No. : 9214233360
OZONOLYSIS: The reaction of alkene of alkene with ozone (O3) followed by hydrolysis is known as
ozonolysis.
It is two types : (I) Reductive ozonolysis  In presence of reducing agent
(II) Oxidative ozonolysis In presence of oxidizing agent
Reducing agents: Zn, H2O or Zn, CH3COOH or (CH3)2S or (Ph)3 P etc.
Oxidising agents: H2O2 or R – C – O – O – H or Ag2 O etc.
||
O
R R’ O3 R O R’ Zn/H2O R
C=C step I C C Reductive C = O + R’– C – H
R H –70°C R H ozonolysis R
O
O O
IR
Oxidative H O
ozonolysis
2 2 [SCT-Cut the double bond
and paste two oxygen atoms
Example 1: and vice versa]
R – C – R + R’ – C – OH
O O
Mechanism:
.S R
R R R
O O R’
C R—C—O
C O + C=O
+ O+ O +
R H
C R’ — C — O
R’ H O
H
R
R R—C—O
.J
O
C O O
R + O
R’ C R – C – R + R’ – C – H
O=C R’
H H O O
Note : In case of oxidative ozonolysis aldehyde (not ketone) further undergoes oxidation which
N
gives acid as product.
Q.1 Give the product of the following reaction. [ 7 × 2 = 14]

(i)O3 (i)O3
(i) H2C = CH2 
(ii)Zn /H2O
 (ii) CH3 — CH = CH2 
(ii)Zn /H2O

CH3
(i)O3 (i)O 3 
(iii) CH3 – C = CH2 
(ii)Zn /H2O
 (iv) 
(ii)Zn /H O
2
(i)O 3  (i)O
3 
(v) 
(ii)Zn /H O
(vi) 
(ii)Zn /H O
2 2
H
(i)O3
(vii) H2C = CH — CH2 – CH = CH – CH3 
(ii)Zn /H2O

31
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Mob. No. : 9214233360
Q.2 Find out the structure of reactant. [11 × 2 = 22]
H
(i)O
3  CH – CH – (i)O
3 
(i) X 
(ii)Zn /H O 3 2 C–H (ii) X 
(ii)Zn /H O O+ O
2 2
H
O
H O O
(i)O
3  (i)O
3 
(iii) X 
(ii)Zn /H O O+
O (iv) X 
(ii)Zn /H O
+
2 2
H H
(i)O
3 
(v) X 
(ii)Zn /H O O
2
(i)O CH3 H
(vi) X  3  + C=O
(ii)Zn /H O C=O +
2 H3 C H
IR
O
O
O
(i)O
3  (i)O
3 
(vii) X 
(ii)Zn /H O
(viii) X 
(ii)Zn /H O O + HCHO
2 2
C10H12 O
O
O
(ix)
.SX 
(i)O
3  +O=C=O+ O + HCHO
(ii)Zn /H O 2 O
C12H18
O O
(i)O
3 C H O (i)O
3 
(x) C6H4 
(ii)Zn /H O 3 2 3 (xi) X 
(ii)Zn /H O
+ HCHO
2 2
(X) C12H18 O
.J
Q.3 Give the ozonolysis product of the following.

H
O () O
(i) X 3 
 3O (ii)  3 ?
Zn C H Zn /H O
2
N
O
How many species will be formed.
O /
(iii) 3 
Zn /H O
2
How many species will be formed.
Q.4 How many initial ozonoids are possible in given reaction.

(i)O /  (i)O / 
(i) CH2 = CH2  3  (ii) CH3 – CH = CH – CH3  3 
(ii)Zn /H O (ii)Zn /H O
2 2
(i)O / 
(iii) CH3 – CH = CH2  3 
(ii)Zn /H O
2
32
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Mob. No. : 9214233360
Q.1 The reaction conditions leading to the best yield of C2 H5 Cl are
UV light dark, room temperature
(A) C2H6 (excess) + Cl2   (B) C2H6 + Cl2  
UV light UV light
(C) C2H6 + Cl2 (excess)   (D) C2H6 + Cl2  
Q.2 2-Methylbutane on reacting with bromine in the presence of sunlight gives mainly
(A) 1-bromo-3-methylbutane (B) 2-bromo-3-methylbutane
(C) 2-bromo-2-methylbutane (D) 1-bromo-2-methylbutane
HI
Q.3 The major product P in the following reaction is CH2 — CH = CH2 
(A) CH2  CH  CH2 (B) CH3  CH  CH3 (C) CH3CH2CH2 I (D) CH2  CH2
| | | |
I I I I
Q.4 An alkane, C6H14 gives two monochloroalkanes when chlorinated. What is the structure of the original
IR
alkane ?
(A) 2, 2-dimethylbutane (B) 2, 3-dimethylbutane
(C) 2 – methylpentane (D) 3 methylpentane
Q.5 When 2-methylbutane is chlorinated, the percentage of (CH3)2 — CH2 — CH2 — CH2Cl is nearly
assuming reactiveity ratio of 3°H : 2°H : 1° H = 5 : 3. 8 : 2.
(A) 28% (B) 35% (C) 23% (D) 14%
.S
Q.6 Which of the following has the highest reaction rate when treated with bromine in a nonpolar solvent?
(A) 2-methylpropane (B) ethane
(C) propane (D) 2, 3 – dimethyl – 2, 2 – butene
Q.7 When 2- butyne is treated with dil. H2SO4 / HgSO4, the product formed is
(A) 2 – butanone (B) Butanol – 1 (C) Butanal (D) Butanol-2
HgSO4
.J
Q.8 Ph — C  C — CH3 + H2O 

H2 SO4

O OH
Ph OH Ph
Ph Ph
(A) (B) (C) (D)
O
N
H2O
Q.9 
H
 Product (major)
Product is:
OH OH
OH
(A) (B) (C) (D)
OH
Q.10 The number of structural and configurational isomers of a bromo compound, C5H9Br formed by the
addition of HBr to 2-pentyne respectively are
(A) 1 and 2 (B) 2 and 4 (C) 4 and 2 (D) 2 and 1
33
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Mob. No. : 9214233360
O CHO
Q.1
CHO
CHO O
is obtained by the ozonolysis of following?
(A) (B) (C) (D)
IR
Q.2 Which starting material should be used to produce the compound shown below?
H
O3 O O
?  H
.S ZnH2O
O
O
(A) (B) (C) (D)
CH3
| O3
H  (A) 
.J
Q.3 CH3 — C — CH3 

  (P) + HCHO
| Zn,H2O
OH
Product (P) is
O
||
N
(A) CH3 — CH2 — CHO (B) CH3 — C — CH3

(C) CH3 — CH — OH (D) CH3 — CHO
|
CH3
Q.4 The reactants that lead to product (a) and (b) on ozonolysis are
O O
HCHO
CHO
(a) (b)
(A) (B) (C) (D)
34
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Mob. No. : 9214233360
Q.5 This compound on ozonolysis gives which of the following compounds
O
O O
O O
(I) (II) OHC—C—C—CH2—C—CHO
O O O O
O
O
(III) (IV) OHC—C—C—CH2—CH = O
IR
O
(A) I, II, III & IV (B) I, III, IV (C) I, II, III (D) I, II, IV
Q.6 Which of the following will give three different compounds on ozonolysis
Me Me
(A) (B) (C) (D)

.S
Q.7 Which one of the following compounds gives acetone (CH3)2C=O as one of the products of its
ozonolysis?
(A) (B) (C) (D)
ozonolysis
Q.8 Sentene 
.J
O O
Which is the correct structure of Sentene.
(A) (B) (C) (D)
Q.9 In which of following reaction product formed is aromatic

N
OH
(A) HBr
 (B) HF 

 
OH
KH  H2SO4
(C) 
 (D) 

HO
OH
Q.10 Propane reacts with chlorine in sunlight to give two products. 1-chloropropane is obtained in 44% yield
and 2-chloropropane is obtained in 56% yield of the total product. 2-Methylpropane reacts with chlorine
under same conditions to produce 1-chloro-2-methylpropane 66% and 2-chloro-2-methylpropane 33%
What will be the percent yield (X) of the major product obtained when 1,3,5-trimethylclohexane is
treated with Cl2 in similar conditions. (Round answer to nearest integer)
35
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Reaction Intermediate (Free Radical and Carbocation) Question Bank PDF

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Reaction Intermediate (Free Radical and Carbocation) Question Bank PDF

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ETOOSINDIA

INDIA’S NO. 1 ONLINE COACHING

IIT-JEE ChEmistry by N.J. sir

(Free Radical &

Q.2 Identify major products.

Mechanism:– (Free radical Mechanism)

(2) R — X + 2e–  R + X

Q.1 CH3 — Cl  Na  _ _ _ _ _ _ _

Q.8 Na/ ether  _ _ _ _ _ _ _ _ _

2. Which of following is correct matching of energy profile diagram?

7. R & S-2-chloro butane

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

(r) CH3CH2CH2 (s) (CH3)2 CH CHCH3

(A) an heating isomerizes to (B). What is the structure of (B).

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

Sum of -hydrogen (A + B + C) is.

7. Sum of -hydrogen in major product of the reaction.

Sum of -hydrogen is A+B+C+D=

8. In which of following reaction resonance stabilized product will form.

(b)  __________

(c)  __________

(e)  ________

(g) Ph—CH2—CH2  _______

(i) Ph—C— CH—CH2—CH2  _______

(k)  _________

(m)   _________

(o) CH3— C — C = O:  _________

(s)  ________

(t)  _________

(u)  _______ _

CH = CH2 CH = CH2 CH = CH2 CH = CH2 CH = CH2

(a) (b) (c)

Q.2 Predict the major product of acied-catalyzed dehydration of alcohols

Q.4 Write – Mechanism

Q.5 Predict Major Product

Q.2 Find total product in following reaction ? (including stereoisomer)

(f) CH3 — CH = CH — CH3 (g) HO CH = CH2

(h) CH3 — CH — CH2 — CH = CH2 (i)

Q.3 Write – Mechanism

Diazotization of primary amine:–

Q.2 CH2 = CH2

gives acid as product.

Q.1 Give the product of the following reaction. [ 7 × 2 = 14]

Q.3 Give the ozonolysis product of the following.

How many species will be formed.

Q.4 How many initial ozonoids are possible in given reaction.

Q.8 Ph — C  C — CH3 + H2O 

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

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

Q.3 CH3 — C — CH3 

(A) CH3 — CH2 — CHO (B) CH3 — C — CH3

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

(III) (IV) OHC—C—C—CH2—CH = O

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

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

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

Q.9 In which of following reaction product formed is aromatic

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