Organic Reaction Mechanisms-II APSP PDF

Organic Reaction Mechanisms-II
 Marked questions are recommended for Revision.

This Section is not meant for classroom discussion. It is being given to promote self-study
and self testing amongst the Resonance students.
PART - I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))

Max. Time : 1 Hr. Max. Marks : 120
Important Instructions
1. The test is of 1 hour duration.
2. The Test Booklet consists of 30 questions. The maximum marks are 120.
3. Each question is allotted 4 (four) marks for correct response.
4. Candidates will be awarded marks as stated above in Instructions No. 3 for correct response of each
question. ¼ (one fourth) marks will be deducted for indicating incorrect response of each question. No
deduction from the total score will be made if no response is indicated for an item in the answer sheet.
5. There is only one correct response for each question. Filling up more than one response in any
question will be treated as wrong response and marks for wrong response will be deducted accordingly
as per instructions 4 above.
X
1.  Br
x is :
(1) Br2 / H2O (2) HBr (3) HBr / Peroxide (4) NBS
2. Which of the following reactions is not an electrophilic addition reactions –
Br H /H O
(1) 
2
 (2) 
2
CCl4
HBr (1) Hg(OAc) , H O

(3) 
 (4) 
2 2

R 2O 2 (2) NaBH4
3. The chlorination of Toluene in presence of ferric chloride gives predominatly :

(1) Benzyl chloride (2) m-Chlorotoluene (3) Benzal chloride (4) o-and p-Chlorotoluene
4. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO 3 and conc. H2SO4. In the
nitrating mixture HNO3 acts as a :
(1) Base (2) Acid (3) Reducing agent (4) Catalyst
Light
5. Ethylbenzene + Cl2  major product is :
(1) o- & p-chloroethylbenzene (2) 1-Chloroethylbenzene
(3) 2- Chloroethylbenzene (4) m-Chloroethylbenzene
6. Which of the following is not o, p-directing group?
(1) –NH2 (2) –OH (3) –X(halogens) (4) –CHO
7. Presence of a cyano group in a benzene ring.
(1) Activates the ring towards electrophilic substitution.
(2) Renders the ring basic.
(3) Deactivates the ring towards nucleophilic substitution.
(4) Deactivates the ring towards electrophilic substitution.
8. The relative rates of mononitration of R–C6H5, where R=CH3, –NO2, –OH, –Cl are :
(1) CH3 > OH > NO2 > Cl (2) OH > Cl > CH3 > NO2
(3) OH > CH3 > NO2 > Cl (4) OH > CH3 > Cl > NO2
9. In the free radical chlorination of Methane, the chain initiating step involves the formation of
(1) Chlorine radical (2) Hydrogen chloride (3) Methyl radical (4) Chloromethyl radical.
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ADV ORM II- 39
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10. Which of the following is the major product for the given reaction ?
h
+ Br2 

333 K
(1) 2-Bromo-2-methylpentane (2) 1-Bromo-2-methylpentane
(3) 4-Bromo-2-methylpentane (4) 3-Bromo-2-methylpentane
11. Allylic bromination of an olefin is :

(1) Nucleophilic substitution (2) Electrophilic substitution
(3) Free radical substitution (4) Electrophilic addition.
12. Which of the following is free radical addition reaction ?


(1) + NO2
(2) CH2=CH2 + HBr 

 CH3–CH2–Br
R O
(3) CH3–CH=CH2 + HBr 
2 2
 CH3–CH2–CH2–Br
(4) CH3–CH=CH2 + HCl 
 CH3– CH –CH3
|
Cl
HOCl
13. Ph–CH=CH–CH3 
 X, X is :
(1) (2)
(3) Ph–CH=CH–CH2Cl (4)
H O
14. 
3
 P (major), P is :
(1) (2)
(3) (4)
15. To which of the following compounds Br2 adds most readily.

(1) CH2=CH2 (2) CH3–CH=CH2
(3) CH3–CH=CH–CH3 (4) CH3 – C = CH – CH3.
CH3
ADV ORM II- 40
16. + Br2 P, P will have configuration:
(1) (2) (3) both are true (4) none is true
AlCl
17. 
3

 Major Product
(1) (2) (3) (4)
18. Which is the most reactive alkane towards bromination in presence of sunlight ?
(1) CH3CH3 (2) CH4 (3) CH3CH2CH3 (4)
h
19. CH3–CH2–CH2–CH3 + Cl2 
 Major product :
(1) CH3–CH2–CH2–CH2–Cl (2)
(3) (4)
R O
20. + HBr 
2 2
 Product; Product is :
(1) (2) (3) (4)
21. Which of the following is the predominant product in the reaction of HOBr with propene ?
(1) 2-Bromo-1-propanol (2) 3-Bromo-1-propanol
(3) 2-Bromo-2-propanol (4) 1-Bromo-2-propanol.
ICl
22. Ph–CH=CH2   P, Identify major product 'P' is :
(1) Ph–CH–CH2–CI (2) Ph–CH–CH2–I (3) Ph–CH–CH2–Cl (4) Ph–CH–CH2–I
I Cl Cl I
23. Which of the following reaction is feasible ?
CH Cl/AlCl
(1) 
3 3
 (2)
AlCl
(3) (4) 
3


ADV ORM II- 41
24. o,p-directing group are mostly :
(1) Activating group (2) Deactivating groups
(3) Neutral groups (4) None of these
CH3
| dil. H2SO4
25. CH3 – C – CH  CH2  X
|
CH3
CH3 CH3
| | (i) (AcO)2 Hg, THF, H2O
CH3 – CH – C  CH2   Y
(ii) NaBH4
CH3 CH3
| | (i) B2H6 / THF
CH3 – C  C – CH3  Z
(ii) H2O2 /OH
(1) All three products (X, Y, Z) are different. (2) X and Y are identical but Z is different.
(3) Y and Z are identical but X is different. (4) All three products (X, Y, Z) are identical.
CH2–F
26. + IBr + AlCl3 Product is :
CH2–F CH2–F
CH2–Cl CH2–F
(1) (2) (3) (4)
Br
Cl I
27. When HBr adds to 1-Butene in the presence of benzoyl peroxide, the products is
(1) 1-Bromobutane (2) 2-Bromobutane (3) 1-Bromobutene (4) 2-Bromobutene.
Hg2  /D
28. Ph–CC–CH2–CH3 
 A, A is :
D2SO4 /D2O
(1) (2)
(3) (4)
29.
Which is correct statement about X and Y.

(1) X is product of ionic reaction and Y is product of radical reaction.
(2) X and Y both are product of ionic reaction.
(3) X and Y both are product of radical reaction.
(4) X is product of radical reaction and Y is product of ionic reaction.
30. Which of the following is the best reagent to convert 1-Methylcyclohexene into 2-methylcyclohexanol ?
(1) Dil H2SO4 (2) Hg(OAc)2 / NaBH4, H2O
(3) B2H6/H2O2, (4) Conc. H2SO4
ADV ORM II- 42
Practice Test-1 (IIT-JEE (Main Pattern))

OBJECTIVE RESPONSE SHEET (ORS)
Que. 1 2 3 4 5 6 7 8 9 10
Ans.
Que. 11 12 13 14 15 16 17 18 19 20
Ans.
Que. 21 22 23 24 25 26 27 28 29 30
Ans.
PART - II : NATIONAL STANDARD EXAMINATION IN CHEMISTRY (NSEC) STAGE-I

1. The alkene limonene has the following structure,
What product results from the reaction of limonene and chlorine water ? [NSEC-2000]
(A) (B)
(C) (D)
2. An unknown compound is analyzed to have a molecular mass of 84 and elements has carbon and
hydrogen only. When subjected to chlorination in the presence of light, three monochlorinated products
are isolated. This compound must be [NSEC-2000]
(A) methylcyclopentane (B) cyclohexane
(C) hexane (D) 1,3-dimethylcyclobutane
3. Which of the following is the major product of the following reaction ? [NSEC-2000]
product (major)
(A) 3-bromo-2-methylpentane (B) 2-bromo-2-methylpentane

(C) 1-bromo-2-methylpentane (D) 4-bromo-2-methylpentane
4. The peroxide effect occurs by : [NSEC-2001]
(A) ionic mechanism (B) homolytic fission of double bond
(C) heterolytic fission of double bond (D) free radical mechanism
5. Benzene does not readily undergo [NSEC-2002]
(A) halogenation (B) nitration
(C) sulphonation (D) oxidation.
6. Which compound amongst the following is nitrated with most difficulty ? [NSEC-2002]
(A) nitrobenzene (B) m-dinitrobenzene
(C) phenol (D) quinol.
7. The reaction of toluene with chlorine in the dark and in presence of FeCI 3 gives predominantly.
(A) benzoyl chloride (B) benzyl chloride [NSEC-2002]
(C) m-chlorotoluene (D) a mixture of o-and p-chlorotoluenes.
ADV ORM II- 43
8. In the reaction of chlorine with propene at 450oC, the major product is [NSEC-2003]
(A) (B)
(C) (D)
9. In the nitration of an aromatic compound using a mixture of concentrated nitric acid and sulphuric acid,
the acids respectively function as [NSEC-2003]
(A) an oxdidising agent and an acid (B) a Bronsted and a Lewis acid
(C) a base and an acid (D) an acid and an oxidising agent.
10. Select the major product obtained from the addition of HBr to 1-methylcyclohexene. [NSEC-2005]
(A) 1-bromo-2-methylcyclohexane (B) 6-bromo-1-methylcyclohex-l-ene
(C) 3-bromo-1-methylcyclohex-1-ene (D) 1-bromo-1-methylcyclohexane.
11. Reaction of benzene with isobutylchloride (CH3CH(CH3)CH2CI) in the presence of anhydrous AICI3
yields [NSEC-2005]
(A) tert-butylbenzene (B) iso-butylbenzene
(C) n-butylbenzene (D) chlorobenzene.
12. The reagent system for preparing propan-1-ol from propene is [NSEC-2006]
(A) Hg(OAc)2/H2O followed by NaBH4 (B) H2SO4/H2O
(C) B2H6 followed by H2O2 (D) HCO2H/H2SO4.
13. In Friedel - Craft acylation, the amount of AICI3 that must be taken is [NSEC-2006]
(A) in catalytic amount (B) one equivalent
(C) more than one equivalent (D) amount does not matter.
14. For a Friedel-Craft reaction using AICI3, which compound can be used as solvent, benzene or
nitrobenzene?
(A) nitrobenzene but not benzene (B) benzene but not nitrobenzene [NSEC-2006]
(C) both benzene and nitrobenzene (D) neither benzene nor nitrobenzene.
15. The major product of the following reaction is [NSEC-2006]
(C6H5CO)2 O2
CH3–CH = CH2 + HBr 
(A) CH3–CH2–CH2–Br (B) CH3–CH(Br)–CH3
(C) BrCH2–CH=CH2 (D)
16. The major product formed upon addition of 1 mole of HBr in the following reactions is : [NSEC-2007]
HBr(1 mole)

 Major product ?
(A) (B) (C) (D)
17. Predict the product formed in the following reaction [NSEC-2007]
(A) (B) (C) (D)
ADV ORM II- 44
18. What is the major product that will be formed in the following reacton ? [NSEC-2008]
(A) (B)
(C) (D)
19. The major product in the following reaction is [NSEC-2008]
(A) (B) (C) (D)
20. Identify the alkene which will not provide the following alcohol upon oxymercuration demercuration.
[NSEC-2008]
(A) (B) (C) (D)
anhydrous AlCl
21. The compound X in the reaction, + ICl 
3

 X is : [NSEC-2009]
(A) (B) (C) (D)
22. Cyclohexene reacts with limited amount of bromine in the presence of light to form product X (C 6H9Br).
The statement correct about X is : [NSEC-2010]
(A) It is a racemate. (B) It is a product of an addition reaction.
(C) It is formed through a cationic intermediate. (D) It is optically active.
23. The major product of the following reaction is : [NSEC-2010]
(i) B2H6 , ether (ii) H2O2, NaOH
(CH3)2C=CH–CH 2–CH3 
(A) (B) (C) (D)
24. The compound which does not react with bromine easily at room temperature is [NSEC-2010]
(A) phenol (B) 2-butyne (C) chlorobenzene (D) 1-pentene
ADV ORM II- 45
25. Major product of mononitration of the following compound is [NSEC-2011]
(A) (B)
(C) (D)
26. The product obtained from the following sequence of reactions is [NSEC-2011]
(A) propanal (B) 2-propanol (C) 1-propanol (D) propane

27. The product (P) of the following reaction is [NSEC-2011]
Lewis acid
+ ICl 
 P
CH3
(A) (B) (C) (D)

I
28. Which isomer of xylene can give three different monochloro derivatives? [NSEC-2012]
(A) o-xylene (B) m-xylene
(C) p-xylene (D) xylene cannot give a monochioro derivative
29. [NSEC-2012]
The ‘product’ in the above reaction is :
(A) (B)
(C) (D) This reaction cannot take place
30. [NSEC-2012]
The rate of o-nitration of the above compounds, (I) toluene, (II) 2-D-toluene and (III) 2, 6-D2-toluene are
is in the following order
ADV ORM II- 46
(A) I > II > III (B) II > I > III
(C) III > I > II (D) The rate is the same for all the three compounds
31. [NSEC-2013]
The correct name of the product obtained is

(A) cis-1,2-dibromocyclohexane (B) cis-1,4-dibromocyclohexane
(C) trans-1,2-dibromocyclohexane (D) trans-1,4-dibromocyclohexane
32. Which of the following statements is correct ? [NSEC-2013]
(A) –NO2 group activates the benzene ring for attack of electrophile at ortho and para position.
(B) –NH2 group activates the benzene ring for attack of electrophile at ortho and para position.
(C) Both–NO2 group as well as –NH2 group activate the benzene ring for attack of electrophile at ortho
and para position.
(D) Neither –NO2 group nor –NH2 group activate the benzene ring for attack of electrophile at ortho and
para position.
33. The major product of the following reaction is [NSEC-2014]
Br , FeBr

2 3
(A) (B)
(C) (D)
34. The product ‘N’ of the following reaction is [NSEC-2014]

i) KMnO4 , NaOH,  conc. HNO3
 M 
 N
ii) H3O conc. H2SO4 , 
(A) (B)
(C) (D)
35. The best sequence of reactions for the following conversion is [NSEC-2015]

(A) (i) 1 mol Br2 / FeBr3 (ii) KMnO4, heat (iii) HNO3+H2SO4
(B) (i) HNO3+H2SO4 (ii) 1 mol Br2 / FeBr3 (iii) KMnO4, heat
(C) (i) KMnO4, heat (ii) HNO3+H2SO4 (iii) 1 mol Br2 / FeBr3
(D) (i) 1 mol Br2 / FeBr3 (ii) HNO3+H2SO4 (iii) KMnO4, heat
ADV ORM II- 47
36. 1,3-pentadiene and 1,4-pentadiene are compared with respect to their intrinsic stability and reaction
with HI. The correct statement is: [NSEC-2015]
(A) 1,3-pentadiene is more stable and more reactive than 1,4-pentadiene
(B) 1,3-pentadiene is less stable and less reactive than 1,4-pentadiene
(C) 1,3-pentadiene is more stable but less reactive than 1,4-pentadiene
(D) 1,3-pentadiene is less stable but more reactive than 1,4-pentadiene
37. The hydrocarbon that cannot be prepared effectively by Wurtz reaction is [NSEC-2015]
(A) (B)
(C) (D)
38. The order of reactivity of the following compounds in electrophilic monochlorinatic the most favorable
position is [NSEC-2015]
(I) (II) (III) (IV)
(A) I < II < IV < III (B) III < IV < I < II (C) IV < III < II < I (D) III < II < IV < I
39. The reaction of 1-phenylpropane with limited amount of chlorine in the presence of light gives mainly.
[NSEC-2016]
(A) 4-chloropropylbenzene (B) 1-chloro-1-phenylpropane
(C) 3-chloro-1-phenylpropane (D) 2-chloro-1-phenylpropane
40. 3-Methylpentane on monochlorination gives four possible products. The reaction follows free radical
mechanism. The relative reactivities for replacement of –H are 3º : 2º : 1º = 6 : 4 : 1. [NSEC-2016]
Cl
Cl2
light +
3-Methylpentane A B
Cl
Cl
C Cl
D
Relative amounts of A, B, C and D formed are
(A) 6/31, 16/31, 6/31, 3/31 (B) 16/31, 6/31, 6/31, 3/31
(C) 6/31, 16/31, 3/31, 6/31 (D) 6/31, 3/31, 6/31, 16/31
41. The best sequence of reactions for preparation of the following compound from benzene is
(H3 C) 2HC COCH3 [NSEC-2016]
HO3 S
(A) (i) CH3COCl/AlCl3 (ii) Oleum (iii) (CH3)2CH–Cl (1 mole)/AlCl3
(B) (i) (CH3)2CH–Cl(1 mole)/AlCl3 (ii) CH3COCl/AlCl3 (iii) Oleum
(C) (i) Oleum (ii) CH3COCl/AlCl3 (iii) (CH3)2CH–Cl (1 mole)/AlCl3
(D) (i) (CH3)2CH–Cl(1 mole)/AlCl3 (ii) Oleum (iii) CH3COCl/AlCl3
ADV ORM II- 48
42. In the given compound the order of case with which hydrogen atom can be abstracted from carbons I to
VI is : [NSEC-2017]
IV
II H VI
O C CH3
I H
H3C C C
H
V
CH3
III
(A) I > VI > IV = V > I > III (B) II > I > VI > III > IV = V
(C) II > I > III > VI > IV = V (D) IV > II > I > III > IV = V
43. Addition of bromine to cis-3-hexene gives [NSEC-2017]
(A) racemic dibromide (B) a mixture of diastereomeric dibromides
(C) optically active dibromide (D) meso dibromide
PART - III : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))

Max. Time : 1 Hr. Max. Marks : 66
Important Instructions
A. General %
1. The test is of 1 hour duration.
2. The Test Booklet consists of 22 questions. The maximum marks are 66.
B. Question Paper Format
3. Each part consists of five sections.
4. Section-1 contains 8 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE is correct.
5. Section-2 contains 6 multiple choice questions. Each question has four choices (A), (B), (C) and (D) out
of which ONE OR MORE THAN ONE are correct.
6. Section-3 contains 5 questions. The answer to each of the questions is a single-digit integer, ranging
from 0 to 9 (both inclusive).
7. Section-5 contains 1 paragraphs each describing theory, experiment and data etc. 2 questions relate to
paragraph. Each question pertaining to a partcular passage should have only one correct answer
among the four given choices (A), (B), (C) and (D).
8. Section-5 contains 1 multiple choice questions. Question has two lists (list-1 : P, Q, R and S; List-2 : 1,
2, 3 and 4). The options for the correct match are provided as (A), (B), (C) and (D) out of which ONLY
ONE is correct.
C. Marking Scheme %
9. For each question in Section-1, 4 and 5 you will be awarded 3 marks if you darken the bubble
corresponding to the correct answer and zero mark if no bubble is darkened. In all other cases, minus
one (– 1) mark will be awarded.
10. For each question in Section-2, you will be awarded 3 marks. If you darken all the bubble(s)
corresponding to the correct answer(s) and zero mark. If no bubbles are darkened. No negative marks
will be answered for incorrect answer in this section.
11. For each question in Section-3, you will be awarded 3 marks if you darken only the bubble
corresponding to the correct answer and zero mark if no bubble is darkened. No negative marks will be
awarded for incorrect answer in this section.
SECTION-1 : (Only One option correct Type)

This section contains 8 multiple choice questions. Each questions has four choices (A), (B), (C)
and (D) out of which Only ONE option is correct.
ADV ORM II- 49
HB r
(R)
–O–O –
1. CH=CH NO2
HB r
(S)
P & Q are :
(A) Positional isomer (B) Geometrical isomer (C) Optical isomer (D) Chain isomer
2. What is the product formed in the following reaction.
H
+ 
 Product
(A) (B) (C) (D)
N–Br   Major product (A) ; A is :

light or ROOR
3. + CCl 4
O
Br
(A) (B) (C) (D)

Br Br
Br
4. The reaction of toluene with Cl2 in presence of FeCl3 gives 'X' and reaction in presence of light gives 'Y'
Thus, 'X' and 'Y' are
(A) X = Benzyl chloride, Y = m-chlorotoluene
(B) X = Benzal chloride, Y = o-chlorotoluene
(C) X = m-chlorotoluene, Y = p-chlorotoluene
(D) X = o- and p-chlorotoluene, Y = Trichloromethyl benzene
5. What is correct order of electrophillic addition of following alkene ?
(I) (II) (III) (IV)
(A) II > IV > I > III (B) IV > III > II > I (C) III > I > IV > II (D) I > II > III > IV
6.
X, Y, Z reaction are :
(A) Simple hydration reaction
(B) Hydroboration oxidation, hydration and oxymercuration demercuration
(C) Hydroboration oxidation, oxymercuration demercuration and hydration
(D) Oxymercuration demercuration, hydroboration oxidation and hydration
ADV ORM II- 50
7. The major product of the given reaction is :
HNO3
Major product
H2SO4
(A) (B)
(C) (D)
8. In which reaction incorrect product(s) have been reported.

HCl(g)(–10º C)
(A) CH2= CH–CHO   CH2 – CH2 – CHO
Cl
H2O /H2SO4
(B) CH2= CH–COOH   CH2 – CH2 – COOH
OH
CH3 CH3
CH3OH/ H2SO4
(C) CH3 – C = CH – C – CH3  
 CH3 – CH – CH C – CH3
O OCH3 O

CH3OH/ H
(D) CH3–CH=CH–OCH3  
 CH3 – CH2 – CH – OCH3
OCH3
Section-2 : (One or More than one options correct Type)

This section contains 6 multiple choice questions. Each questions has four choices (A), (B), (C)
and (D) out of which ONE or MORE THAN ONE are correct.
9. In the chlorination of Methane which of the following reaction involve in the chain termination step.
  
(A) Cl – Cl  2 Cl (B) Cl + Cl  Cl–Cl
   
(C) CH3 + Cl  CH3–Cl (D) CH3 + Cl–Cl  CH3–Cl + Cl
10. Which of the following reactions are completed through free radical intermediate ?
h
(A) (CH3)3CH + Br2 
 (CH3)3CBr + HBr
Br Br
(B) (CH3)3C=CH2 + Br2 CH3–C–CH2
CH3
h
(C) CH3–CH=CH2 + Cl2 

R O
(D) Ph–CH=CH2 + HBr 
2 2
 Ph–CH2–CH2
h
Br
ADV ORM II- 51
11. Which of the following statements are correct for give reaction.
Br Br
CH3–C=CH–CH3 + HBr 

 CH3–C–CH2–CH3
Peroxide
CH3–CH–CH–CH3
CH3 CH3 CH3

(A) Major product is mixture of two enantiomers.
(B) Less stable carbocation give major product.
(C) Less stable free radical give major product.
(D) More stable free radical give major product.
12. In which of the following reaction reactants and products are correctly matched ?
(A) F3C–CH=CH2 + HCl  
(B) 

ROOR
(C) C6H5CH = CHCH3 + HBr 

(D)
13. Which statement is /are correct.

(A) No primary kinetic isotope effect is observed during nitration of benzene
(B) KH/ KD = 1 for halogenation of benzene
(C) KH / KD = 1 for sulphonation of benzene
(D) KH/KD is > 1 for alkylation of benzene
14. Which of the following statements is/are incorrect ?

(A) Nitrobenzene will give meta-nitrotoluene on reaction with CH3Cl/AlCl3.
(B) Chlorobenzene will give meta-substituted product on electrophilic substitution since it exerts –I > +
M effect.
(C) n-Propyl benzene can be easily obtained on Friedal crafts alkylation of benzene with n-propyl
chloride.
(D) Toluene can be obtained in better yield when excess of benzene will react with CH3Cl/AlCl3.
Section-3 : (Single/ Double Integer Value Correct Type.)

This section contains 5 questions. Each question, when worked out will result in one integer
from 0 to 9 (both inclusive)
15. How many of the following substituents can cause aromatic electrophilic substitution faster than
benzene ?

(a) –NH2 (b) –NR2 (c) –NO2 (d) – NH3
O O O O
|| || || ||
(e) –O – C – R (f) –NH – C – R (g) –C – Cl (h) –C – H
(i) –SO3H (j) –CH3 (k) –CH = CR2
ADV ORM II- 52
16. How many alkenes react faster than propene with dil.H2SO4?
Ph
Ph CH3 O
(a) (b) (c) (d)
Ph
H2 N O
(e) (f) (g) (h) Cl
17. When addition of Br2 was carried out in presence of aq. NaCl on ethene then total number of possible
product are :
18. How many reactions will proceed through free radical addition mechanism ?
NBS HCl
(i)  (ii) 

R 2O 2
HBr HI
(iii) CH3–C=CH–CH3 
 (iv) CH3–CC–CH2–CH3 
h R 2O 2
CH3
CH=CH–CH3
HBr NBS
(v) CH3–CH=CH2 
 (vi) 
R 2O 2
19. In the given reactions M is the number of major products obtained in Ist reaction and N number of major
products obtained in IInd reaction. Report your answer as .
CH2CH3
(1) Hg(OAc) , H O
(i) 
2 2
 M
(2) NaBH4
H
CH2CH3
(1) BH .THF
(ii) 
3
N
H (2) H2O2OH
SECTION-4 : Comprehension Type (Only One options correct)

This section contains 1 paragraphs, each describing theory, experiments, data etc. 2 questions
relate to the paragraph. Each question has only one correct answer among the four given
options (A), (B), (C) and (D)
Paragraph for Question Nos. 20 to 21

Consider experimental data shown in this table :
Alkene Relative rate Alkene Relative rate
CH2=CH2 1 (CH3)2C=CH2 5,400
CH2=CH–CH3 61 (CH3)2C=CHCH3 130,000
H CH3
C=C 1700 (CH3)2C=C(CH3)2 1,800,000
H3C H
H H
C=C 2600
H3C CH3
ADV ORM II- 53
20. Rate of electrophilic addition on isobutylene is significantly higher than cis or trans-2-Butene chiefly due
to –
(A) Lesser stability of (isobutylene) in comparison to or .
(B) Higher dipole moment of in comparison to cis or trans-2-Butene.

(C) Better stabilization of positive charge acquired during formation of bromonium ion intermediate by
Me-groups
(D) High angle strain in the molecule
21. Which of the following would be expected to have highest rate of electrophilic addition of Br 2 ?
(A) Ph–CH=CH2
Ph
(B) C=CH2
H3C
(C) Ph–CH=CH–CH3
(D) All react with the same rate, since the rate depends only on [Br 2] and not on the substrate.
SECTION-5 : Matching List Type (Only One options correct)

This section contains 1 questions, each having two matching lists. Choices for the correct
combination of elements from List-I and List-II are given as options (A), (B), (C) and (D) out of
which one is correct
22. Match List-I (Compounds) with List-II (% meta electrophilic substitution product) and select the correct
answer using the code given below the lists:
List-I List-II
(P) Ar–CH3 (1) 64.6
(Q) ArCH2Cl (2) 34
(R) ArCHCl2 (3) 4.5
(S) ArCCl3 (4) 15
Codes :
P Q R S P Q R S
(A) 1 3 2 4 (B) 3 4 2 1
(C) 4 2 3 1 (D) 2 1 3 4
Practice Test-2 ((IIT-JEE (ADVANCED Pattern))

OBJECTIVE RESPONSE SHEET (ORS)
Que. 1 2 3 4 5 6 7 8 9 10
Ans.
Que. 11 12 13 14 15 16 17 18 19 20
Ans.
Que. 21 22
Ans.
ADV ORM II- 54
PART - I
1. (4) 2. (3) 3. (4) 4. (1) 5. (2)
6. (4) 7. (4) 8. (4) 9. (1) 10. (1)
11. (3) 12. (3) 3. (2) 14. (3) 15. (4)
16. (2) 17. (2) 18. (4) 19. (2) 20. (3)
21. (4) 22. (2) 23. (3) 24. (1) 25. (4)
26. (4) 27. (1) 28. (3) 29. (1) 30. (3)
PART - II
1. (D) 2. (D) 3. (B) 4. (D) 5. (D)
6. (B) 7. (D) 8. (C) 9. (C) 10. (D)
11. (A) 12. (C) 13. (C) 14. (A) 15. (A)
16. (B) 17. (B) 18. (B) 19. (A) 20. (D)
21. (B) 22. (A) 23. (D) 24. (C) 25. (D)
26. (B) 27. (B) 28. (B) 29. (B) 30. (D)
31. (C) 32. (B) 33. (B) 34. (A) 35. (A)
36. (A) 37. (B) 38. (B) 39. (B) 40. (C)
41. (B) 42. (B) 43. (A)
PART - III
1. (A) 2. (A) 3. (C) 4. (D) 5. (C)
6. (C) 7. (D) 8. (C) 9. (BC) 10. (ACD)
11. (AD) 12. (BCD) 13. (AB) 14. (ABC)
15. 6 (a, b, e, f, j, k) 16. 6 (a, b, c, d, e, g) 17. 3
18. 2 19. 12 20. (C) 21. (B) 22. (B)
ADV ORM II- 55
PART - I
1. It is allylic substitution reaction.
2. Reaction A is free radical addition reaction and all are electrophilic addition reactions.
1
7. EAS  on Benzene ring.
EWG
8. In presence of +M effect rate of mononitration increase and in presence of –M effect rate will
decreases.
14. As in previous question.

23. Reaction is possible in option (3) only.
CH3
|
dil. H2SO4
CH3 – C – CH  CH2 
25. 
 

|
CH3
(i) (AcO) Hg, THF, H O


2 2

(ii) NaBH4
(i) B H / THF

2 6

(ii) H2O2 /OH
All products are identical.
26. [AlCl3Br]– + I
(i) I
  
(ii) AlCl3Br
Minor Major
29. In the presence of peroxide, HBr undergoes free radical addition and HCl undergoes electrophilic
addition, because of H–Cl bond have high bond energy.
ADV ORM II- 56
PART - III
1. P= CH2–CH NO 2 ; Q = CH–CH2 NO 2
Br Br
H  
H¯ shift
2. 
 +
+
+ + H+ H
+
3. The given reaction occur via free radical substitution mechanism. Major product will depend on the
stability of free radical.
4.
5. Electron releasing group and stability of carbocation/halonium ion will decide rate of reaction in
electrophilic addition reaction.
6. X = Hydrobroation oxidation, Y = oxymercuration & demercuration, Z = Simple hydration reaction
HNO3
7. H2SO4
–C group is more ring activity than , para position wrt –CH3 group is more crowded than ortho.
8. The more stable carbocation of alkene gives the major product in electrophilic addition reactions.
9. Option ‘D’ is chain propagating step.
14. (A) In highly de-activated ring Friedal Crafts reaction is not possible.
(B) Chloro group is ortho-para director.
(C) In Friedal Craft reaction the electrophile carbocation rearranges.
(D) To avoid polyalkylation aromatic substrate is taken in excess.
16. Rate of E addition  stable cation
ADV ORM II- 57
Br 
H H H H
C C Br2 aq.NaCl C C
17. 

H H H H
Br
Cl
OH 
Br Br Br
H H H H H H
C C + C C + C C
H H H H H H
Br Cl OH
Formation of these three products clearly indicates about formation of cyclic Bromonium ion.
18. Only (iii) & (v)
CH2CH3
CH2CH3
(1) Hg(OAc) , H O OH
19. 
2 2
 H
(2) NaBH4
H
H
Single product
m=1
CH 2CH 3 CH 2CH 3
CH2CH3
(1) BH .THF H H

3
 +
(2) H2O2OH OH OH
H
H H
n=2
22. EWG groups are meta directing.
ADV ORM II- 58

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Organic Reaction Mechanisms-II

 Marked questions are recommended for Revision.

PART - I : PRACTICE TEST-1 (IIT-JEE (MAIN Pattern))

HBr (1) Hg(OAc) , H O

3. The chlorination of Toluene in presence of ferric chloride gives predominatly :

11. Allylic bromination of an olefin is :

12. Which of the following is free radical addition reaction ?

(2) CH2=CH2 + HBr 

(3) Ph–CH=CH–CH2Cl (4)

15. To which of the following compounds Br2 adds most readily.

16. + Br2 P, P will have configuration:

(1) (2) (3) both are true (4) none is true

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

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

Which is correct statement about X and Y.

Practice Test-1 (IIT-JEE (Main Pattern))

PART - II : NATIONAL STANDARD EXAMINATION IN CHEMISTRY (NSEC) STAGE-I

(A) 3-bromo-2-methylpentane (B) 2-bromo-2-methylpentane

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

17. Predict the product formed in the following reaction [NSEC-2007]

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

19. The major product in the following reaction is [NSEC-2008]

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

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

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

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

(A) propanal (B) 2-propanol (C) 1-propanol (D) propane

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

The ‘product’ in the above reaction is :

(C) (D) This reaction cannot take place

The correct name of the product obtained is

34. The product ‘N’ of the following reaction is [NSEC-2014]

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

PART - III : PRACTICE TEST-2 (IIT-JEE (ADVANCED Pattern))

SECTION-1 : (Only One option correct Type)

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

N–Br   Major product (A) ; A is :

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

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

8. In which reaction incorrect product(s) have been reported.

Section-2 : (One or More than one options correct Type)

CH3–C=CH–CH3 + HBr 

CH3 CH3 CH3

13. Which statement is /are correct.

14. Which of the following statements is/are incorrect ?

Section-3 : (Single/ Double Integer Value Correct Type.)

SECTION-4 : Comprehension Type (Only One options correct)

Paragraph for Question Nos. 20 to 21

(A) Lesser stability of (isobutylene) in comparison to or .

(B) Higher dipole moment of in comparison to cis or trans-2-Butene.

SECTION-5 : Matching List Type (Only One options correct)

Practice Test-2 ((IIT-JEE (ADVANCED Pattern))

1. (4) 2. (3) 3. (4) 4. (1) 5. (2)

6. (4) 7. (4) 8. (4) 9. (1) 10. (1)

11. (3) 12. (3) 3. (2) 14. (3) 15. (4)

1. (D) 2. (D) 3. (B) 4. (D) 5. (D)

6. (B) 7. (D) 8. (C) 9. (C) 10. (D)

41. (B) 42. (B) 43. (A)

1. (A) 2. (A) 3. (C) 4. (D) 5. (C)