BKBK

PREVIOUS YEAR
PROBLEM SOLVING
IIT JEE MAIN + ADVANCED
ORGANIC CHEMISTRY
BY
NAVNEET JETHWANI
HALOGEN
DERIVATIVE
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA N.J. SIR
JEE MAINS
1. Following reaction (CH3)3CBr + H2O  (CH3)3COH + HBr
is an example of : [AIEEE-2002]
(1) Elimination reaction (2) Free radical substitution
(3) Nucleophilic substitution (4) Electrophilic substitution
Ans. (3)
2. SN1 reaction is feasible in : [AIEEE-2002]
CH3
Cl
(1) CH3 C Cl + KOH(aq)  (2) + KOH(aq) 
CH3
(3) Cl + KOH (aq)  (4) CH2CH2 Cl + KOH (aq) 
Ans. (1)
3. Bottles containing C6H5I and C6H5–CH2I lost their original lables. They were labelled A and B for testing. A and B
were separately taken in a test tube and boiled with NaOH solution. The end solution in each tube was made acidic
with dilute HNO3 and then some AgNO3 solution was added. Substance B gave a yellow precipitate. Which one of
the following statement is true for this experiment. [AIEEE-2003]
(1) A was C6H5 I (2) A was C6H5CH2I
(3) B was C6H5I (4) Addition of HNO3 was unnecessary
Ans. (1)
4. The compound formed on heating chlorobenzene with chloral in the presence of concentrated sulphuric acid is-
[AIEEE-2004]
(1) Gammaxe (2) DDT (3) Freon (4) Hexa chloro ethane
Ans. (2)
5. Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of : [AIEEE-2005]
(1) steric hindrance (2) inductive effect (3) instability (4) insolubility
Ans. (1)
6. Reaction of trans 2–phenyl –1 – bromocyclopentane on reaction with alcoholic KOH produces: [AIEEE-2006]
(1) 2–phenylcyclopentene (2) 1–phenylcyclopentene
(3) 3-phenylcyclopentene (4) 4-phenylcyclopentene
Ans. (3)
7. The structure of the major product formed in the following reaction is : [AIEEE-2006]
CH 2Cl
NaCN


DMF

CHCl
2 CH2Cl CHCN
2 CH2CN
(1) NC (2) (3) (4)

 CN  CN
Ans. (3)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
ETOOSINDIA N.J. SIR
8. Which of the following is the correct order of decreasing SN2 reactivity ? [AIEEE-2007]
(1) RCH2X > R3CX > R2CHX (2) RCH2X > R2CHX > R3CX
(3) R3CX > R2CHX > RCH2X (4) R2CHX > R3CX > RCH2X
Ans. (2)
9. Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(1) CH2ClCH2Cl (2) CH3CHCl2 (3) CH3COCl (4) CH3CH2Cl
Ans. (2)
10. Consider the following bromides : [AIEEE-2010]
Me Me
Me Br Me
Br Br
(A)
(B) (C)
The correct, order of SN1 reactivity is

(1) B > C > A (2) B > A > C (3) C > B > A (4) A > B > C
Ans. (1)
11. A solution of ( – ) – 1 – chloro–1–phenylethane in toluene racemises slowly in the presence of a small amount of
SbCl5, due to the formation of : [JEE MAINS 2013]
(1) carbanion (2) carbene (3) carbocation (4) free radical
Ans. (3)
12. In a nucleophilic substitution reaction : [JEE MAINS (Online) 2014]
R  Br  Cl 
DMF
 R  Cl  Br 
Which one of the following undergoes complete inversion of configuration ?
(1) C6H5CCH3C6H5Br (2) C6H5CHCH3Br (3) C6H5CHC6H5Br (4) C6H5CH2Br
Ans. (2)
13. The major product obtained in the photo catalysed bromination of 2-methylbutane is :-
[JEE MAINS (Online) 2014]
(1) 2-bromo-2-methylbutane (2) 2-bromo-3-methylbutane
(3) l-bromo-2-methylbutane (4) l-bromo-3-methylbutane
Ans. (1)
14. The major product formed when 1,1,1 - trichloro- propane is treated with aqueous potassium hydroxide is :
(1) 2 - Propanol (2) Propionic acid (3) Propyne (4) 1 - Propanol
Ans. (2)
15. In the presence of a small amount of phosphorous, aliphatic carboxylic acids react with chlorine or bromine to
yield a compound in which  - hydrogen has been replaced by halogen. This reaction is known as :
(1) Wolff - Kischner reaction (2) Etard reaction
(3) Hell - Volhard - Zelinsky reaction (4) Rosenmund reaction
Ans. (3)
ETOOSINDIA N.J. SIR
16. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields : [JEE MAINS 2016]
(a) (b) (c)
(1) (a) and (c) (2) (c) only (3) (a) and (b) (4) All of these
Ans. (4)
17. The product of the reaction given below is : [JEE MAINS 2016]
1. NBS/hv
2. H 2O /K 2CO 3
X
CO2H OH O
(1) (2) (3) (4)
Ans. (3)
18. The reaction of propene with HOCl (Cl2 + H2O) proceeds through the intermediate : [JEE MAINS 2016]
(1) CH3 – CHCl – CH2+ (2) CH3–CH+–CH2–OH (3) CH3–CH+ – CH2–Cl (4) CH3–CH(OH)–CH2+
Ans. (3)
19. Bromination of cyclohexene under conditions given below yields : [JEE MAINS (Online) 2016]
Br2/h
Br
Br
Br Br
(1) (2) (3) (4)

Br Br
Br
Ans. (2)
20. Which one of the following reagents is not suitable for the elimination reaction ? [JEE MAINS (Online) 2016]
Br
(1) NaOH/H2O (2) NaOEt/EtOH (3) NaOH/H2O-EtOH (4) NaI

Ans. (4)
ETOOSINDIA N.J. SIR
21. The increasing order of the reactivity of the following halides for the SN1 reaction is : [JEE MAINS 2017]
CH 3CH CH 2CH 3
CH3CH2CH2Cl p-H2CO C 6H4 CH2Cl
Cl
(II) (III)
(I)
(1) (III) < (II) < (I) (2) (II) < (I) < (III) (3) (I) < (III) < (II) (4) (II) < (III) < (I)
Ans. (2)
22. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolourize
the colour of bromine ? [JEE MAINS 2017]
O C6H5
(1) (2)
Br Br
O
O
(3) (4)
Br Br
Ans. (1)
23. 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition product. The number of
possible stereoisomers for the product is : [JEE MAINS 2017]
(1) Six (2) Zero (3) Two (4) Four
Ans. (4)
24. The major product obtained in the following reaction is : [JEE MAINS 2017]
Br
H BuOK
C 6H 5

C 6H 5
(1) (±) C6H5CH(OtBu)CH2C6H5 (2) C6H5CH=CHC6H5

t
(3) (+) C6H5CH(O Bu)C2H5 (4) (–) C6H5CH(OtBu)CH2C6H5
Ans. (2)
25. In the following reaction sequence :
I KOH(aq) (i) CH3MgBr Anhy. ZnCl2+ Conc. HCl
(C3H6Cl2) II III gives turbidity
(ii) H2O/H+ immediately
The compound I is [JEE MAINS (Online) 2017]
Cl
(1) CH3 C CH3 (2) Cl CH CH2 CH3
Cl Cl
CH2 CH CH3 CH2 CH2 CH2

(3) (4)
Cl Cl Cl Cl
Ans. (1)
ETOOSINDIA N.J. SIR
26. The major product of the following reaction is : [JEE MAINS (Online) 2017]
Br2/h
Br
Br
Br
(1) (2) (3) (4)
Br
Br
Ans. (1)
OH 1. K2CO3
2. CH 3I (1.eq.)
OH
OCH3 OH
(1) (2)
OH OCH3
O OCH3
(3) (4)
Ans. (1)
CH3
C2H5ONa
C6H5CH2 C CH2 CH3
C2H5OH
Br
(1) C6H5CH C CH 2 CH3 (2) C6H5CH2 C CHCH3

CH3 CH3
CH3
(3) C6H5CH2 C CH2CH3 (4) C6H5CH2 C CH2
OC2H5 C H2CH3
Ans. (1)
ETOOSINDIA N.J. SIR
JEE ADVANCED
SUBJECTIVE TYPE
1. Fill in the blanks :
(a) Butane nitrile can be prepared by heating _______ with alcoholic KCN. [IIT 1992]
(b) Amongst three isomers of nitrophenol, the one that is least soluble in water is ______. [IIT 1992]
Ans. (a) propyl chloride (b) ortho
2. Arrange the following in order of their [IIT 1992]
(i) Increasing basicity
H2O, OH–, CH3OH, CH3O–
(ii) Increasing reactivity in nucleophilic substitution reactions
CH3F, CH3I, CH3Br, CH3Cl
Ans. (i) H2O < CH3OH < HO– < CH3O– (ii) CH3F < CH3Cl < CH3Br < CH3I
3. Write the structures of the major organic product expected from each of the following reactions : [IIT 1992]
CH3
Alc. KOH aq. alkali
(i) H3C CH2CH3 (ii) CH3CH 2CHCl2
 boil
Cl
CH3 OH
Ans. (i) CH3 C CH CH3 (ii) CH 3 CH 2 CH OH (Unstable), CH3CH2CHO

4. Identify the major product in the following reactions : [IIT 1993]
H
Alc. KOH HBr
C6H5 CH2 CH3 ? ?

Br
Ans. C6H5 – CH = CH – CH3, C6H5 CH CH2 CH3
Br
5. Identify the major product in the following reactions : [IIT 1993]
Cl
(i) Alc. KOH HBr
C6H5 CH2 CH CH3 ? ?

(ii) C6H5COOH + CH3MgI  ? + ?
Br
Ans. (i) C6H5 – CH = CH – CH3 ; C6H5 CH CH2 CH3 (ii) C6H5COOMgI + CH4
6. Aryl halides are less reactive then alkyl halides towards nucleophilic reagents. Give reason. [IIT 1994]
X X+
Ans.
aryl halide
Due to the above resonance phenomena, C–X bond acquire partial double bond character and becomes difficult
to break in the rate determining step of SN2 reaction.
ETOOSINDIA N.J. SIR
7. Draw the stereochemical structure of the products in the following reaction. [IIT 1994]
CH3
Θ
OH/DMSO
Br H 
S
N2
C2H5
Ans. SN2 reactions leads to inversion of configuration at a–C.
CH3
H OH
C2H5
Product with inverted
configuration
8. Optically active 2-iodobutane on treatment with NaI in acetone gives a product which does not show optical
activity. Explain briefly. [IIT 1995]
CH3 CH3
Ans. C I+I I C H
H
C2H5
C2H5
Above equilibrium is established which has equilibrium constant equal to 1. Therefore, equilibrium mixture will have
both the enantiomers in equal amount giving racemic mixture.
9. An alkyl halide X of formula C6H13Cl on treatment with potassium tertiary butoxide gives two isomeric alkenes Y
and Z (C6H12). Both alkenes on hydrogenation give 2,3–dimethylbutane. Predict the structures of X, Y and Z.
[IIT 1996]
CH3 CH3 CH3 CH3
Ans. (X) : CH3 C CH CH3 (Y) : CH2 C CH CH3 (Z) CH2 C CH CH 3
Cl CH 3 CH 3
10. Predict the structure of intermediates/products in the following reaction sequence – [IIT 1996]
Br
H Ph
NaI
MeO H C
Acetone
Ph
I
H Ph
Ans. MeO H (NGP due to MeO, so retention of configuration)
Ph
11. Which of the following is the correct method for synthesising methyl-t-butyl ether and why ? [IIT 1997]
(CH3)3 CBr + NaOMe  or CH3Br + NaO-t-Bu 
CH3
E2 CH3 CH3 CH3
CH3 C Br + CH3O CH3 C SN2
Ans. ; CH3 C O + CH3Br CH3 C OCH3
CH3
CH3
CH3 CH3
ETOOSINDIA N.J. SIR
12. Write the structures of the products : [IIT 1998]

Alc.KOH
C 6 H 5 CH 2CHClC6 H 5 

Alc. KOH
Ans. C6 H 5 CH2 CH C 6H 5 C 6H 5 CH CH C 6H 5
E2
Cl
HI (excess)
13. (CH3)2CHOCH 3 A+B Write the structures of (A) and (B) [IIT 1998]
Heat
CH3
Ans. CHI + CH3I
CH3
14. Complete the following reaction with appropriate structures of products/reagents. [IIT 1998]
CH CH2
Br2 (i) NaNH2(3 equi.)

(A) (B)
(ii) CH3I
Br CH3I C CCH3
NaNH2(liq.) C CNa (B)
CH CH2Br
Ans. (A)
15. What would be major product ? [IIT 2000]
CH3
CH3 C CH2Br C2H5OH


CH3
CH3
Ans. CH3 C CHCH3 E1 reaction
16. Which would be the major product in each of the following reactions ? [IIT 2000]
CH3
C2 H 5 OH
(A) H3C 

CH3
F
NaOCH 3
(B) 


NO2
ETOOSINDIA N.J. SIR
(C) base
 

O
Br
OCH3
CH 3
Ans. (a) (b) (c)
H 2C—C=CH—CH 3 O
NO2
17. Identify X, Y and Z in the following synthetic scheme and write their structures [IIT 2002]
(i) NaNH2 H2/Pd-BaSO4 alkaline

CH3CH2CCH X Y Z
(ii) CH3CH2Br KMnO4
(i) NaNH 2
Ans. CH3CH2 C CH CH3CH2 C C CH3CH2
(ii) CH3CH2Br
C2H5
H2/Pd-BaSO4 H H Alk. KMnO4 H OH
X C C
H OH
C2H5 C2H5
C2H5
mesodiol
18. Give major products A, B, C and D in following reaction sequence. [IIT 2002]
CH2 Cl

KCN (i) NaOEt/EtOH H3O
(A) (B) (C)
DMF (ii) PhCHO/
(i) SOCl2
(ii) CH3NH2
CN COOH
CH2 CN CH C CH2 C
Ans. (A) ; (B) ; (C)
CONHCH3
CH C
(D)
ETOOSINDIA N.J. SIR
19. Give reasons : [IIT 2005]
H3C Br
CH3
C 2 H 5OH(aq.) C H 5OH(aq.)
(A) (i)      acidic solution ; (ii) Br— 2     neutral
CH3 CH3
F F
NaOH(aq) NaOH(aq)
(B) (i) O N     F– (liberated) ; (ii)  F– is not liberated
  
2 H3C
CH3 CH2NO2
CH3
—C—OC2H5
Ans. (A) (i) Products are + HBr (aq.) ; Hence acidic.
CH3
(ii) No reaction takes place, as aryl halide is inert to nucleophilic subsititution.

(B) (i) —NO2 group facilitates the nucleophilic attack because it stabilised the anion formed when attack of
OH takes place. (ii) Does not show reaction.
20. The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the following
compound, is [IIT 2011]
CH3
C
CH3CH2 CH2CH3
H
Ans. (8)
21. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH
is [IIT-2011]
Ans. (5)
Br
C C C C C C C C C C C C C C C C C C C C C C C C
alcoholic
+ +
KOH
1 product 2 products 2 products
(Geometrical isomers) (Geometrical isomers)
22. In the following monobromination reaction, the number of possible chiral products is : [JEE (Advanced) 2016)
CH2  CH2 CH3
Br2 (1.0 mole)
H Br 300 °C
CH3
1.0 mole
(enatiomerically pure)
Ans. (5)
ETOOSINDIA N.J. SIR
Single Objective
23. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH gives-
(A) o-cresol (B) p-cresol [IIT-90]
(C) 2, 4 dihydroxytoluene (D) Benzoic acid
Ans. (D)
24. 1-Chlorobutane on reaction with alcoholic potash gives - [IIT-91]
(A) 1–butene (B) 1–butanol (C) 2–butene (D) 2–butanol
Ans. (A)
25. In the addition of HBr to propene in the absence of peroxides, the first step involves the addition of -
(A) H+ (B) Br– (C) H (D) Br [IIT-93]
Ans. (A)
26. Arrange the following compounds in order of increasing dipole moment : [IIT-96]
(I) Toluene ; (II) m-dichlorobenzene ; (III) o-dichlorobenzene ; (IV) p-dichlorobenzene
(A) I < IV < II < III (B) IV < I < II < III (C) I < IV < III < II (D) IV < II < I < III
Ans. (B)
27. In the reaction of p-chloro toluene with KNH2 in liq. NH3, the major product is - [IIT-97]
(A) o-toluidine (B) m-toluidine (C) m-chloroaniline (D) p-chloroaniline
Ans. (B)
28. (CH3)3CMgCl reaction with D2O produces : IIT-97]

(A) (CH3)3CD (B) (CH3)3OD (C) (CD3)3CD (D) (CH3)3OD
Ans. (A)
29. The intermediate during the addition of HCl to propene in presence of peroxide is - [IIT-97]
+
(A) CH3CHCH2Cl (B) CH3CHCH3 (C) CH 3CHCH 2 (D) CH 3CH 2CH 2
Ans. (B)
30. The number of possible enantiomeric pairs that can be produced during monochlorination of isopentane-
(A) 2 (B) 3 (C) 4 (D) 1 [IIT-1997]
Ans. (A)
31. During debromination of meso-2,3-dibromobutane, with Zn dust/CH3COOH the major compound formed is -
[IIT-1997]
(A) n-butane (B) 1-butene (C) cis-2-butene (D) trans-2-butene
Ans. (D)
32. In the following groups : [IIT-1997]
(I) –OAc ; (II) –OMe ; (III) –OSO2Me ; (IV) OSO2CF3
the order of leaving group ability is -
(A) I > II > III > IV (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I
Ans. (B)
33. Toluene, when treated with Br2/Fe, gives o and p-bromotoluene, because the CH3 group -
(A) is ortho and para directing (B) is meta directing [IIT-1999]
(C) deactivates the ring by hyperconjugation (D) deactivates the ring
Ans. (A)
ETOOSINDIA N.J. SIR
34. The order of reactivity of the following alkyl halides for a S N2 reaction is - [IIT-2000]
(A) RF > RCl > R –Br > R–I (B) R–F > R –Br > R–Cl > R–I
(C) R–Cl > R –Br > R–F > R–I (D) R–I > R –Br > R–Cl > R–F
Ans. (D)
35. Which of the following has the highest nucleophilicity : [IIT-2000]
(A) F– (B) OH– (C) CH3– (D) NH2–
Ans. (C)
36. An S N2 reaction at an asymmetric carbon of a compound always gives : [IIT-2001]
(A) an enantiomer of the substrate
(B) a product with opposite optical rotation
(C) a mixture of diastereomers
(D) a single stereoisomer
Ans. (D)
37. The compound that will react most readily with NaOH to form methanol is [IIT-2001]
(A) (CH3)4N+I– (B) CH3OCH3 (C) (CH3)3S+I– (D) (CH3)3CCl
Ans. (A)
38. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markovnikov's addition to
alkenes because : [IIT-2001]
(A) both are highly ionic
(B) one is oxidising and the other is reducing
(C) one of the steps in endothermic in both the cases
(D) all the steps are exothermic in both the reactions
Ans. (C)
39. Identify the set of reagents/reaction conditions 'X' and 'Y' in the following set of transformations - [IIT-2002]
X Y
CH3–CH2–CH2Br  Product  CH3–CH–CH3
Br
(A) X = dilute aqueous NaOH, 20°C, Y= HBr/acetic acid, 20°C
(B) X = concentrated alcoholic NaOH, 80°C; Y = HBr/acetic acid, 20°C
(C) X = dilute aqueous NaOH 20°C, Y = Br2/CHCl3, 0°C
(D) X = concentrated alcoholic NaOH, 80°C; Y = Br2/CHCl3, 0°C
Ans. (B)
40. CH3MgBr + Ethyl ester  which can be formed as product [IIT-2003]
(excess)
CH2CH3 CH3
(A) HO CH2CH3 (B) HO CH2CH2CH3
CH2CH3 CH2CH3
CH2CH3 CH3
(C) HO CH2CH3 (D) HO CH3
CH3 CH3
Ans. (D)
ETOOSINDIA N.J. SIR
41. The product of following reaction is [IIT-2003]
OH
C2H5O- (excess)
+ C2H5I
C2H5OH
(A) C6H5OC2H5 (B) C2H5OC2H5 (C) C6H5OC6H5 (D) C6H5I

Ans. (B)
(CH3)2NH (i) NaNO2 + HCl 0°–5°C

42. F NO2 (A) (B) [IIT-2003]
DMF (ii) H2/Catalytic Reduction
H 3C
(A) O2N NH2 (B) N NH 2
H 3C
H3C H 3C
(C) N NO2 (D) N NO 2
H2C H 3C
NH2
Ans. (B)
43. The following compound on hydrolysis in aqueous acetone will give: [IIT 2005]
CH3 H CH3
(A) MeO NO2
H Cl CH3
CH3 H CH3
(K) MeO NO2
H OH CH3
CH3 H CH3
(L) MeO NO2
OH H CH3
CH3 H CH3
(M) MeO NO2
H CH3 OH
It mainly gives
(A) K and L (B) Only K (C)L and M (D) Only M
Ans. (A)
ETOOSINDIA N.J. SIR
44. The reagent (s) for the following conversion : [IIT 2007]
Br
?
HC C H is /are -
Br
(A) alcoholic KOH (B) Alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2 (D) Zn/CH3OH
Ans. (B)
45. The major product of the following reaction is [IIT 2008]
H3C Br
F
PhSNa

dim ethyl formamide

NO2
H3C SPh H3C SPh H3C SPh

H3C Br
F F SPh
SPh
(A) (B) (C) (D)
NO2 NO2 NO2

NO2
Ans. (A)
HBr
46. In the reaction OCH3    the products are [IIT 2010]
(A) Br OCH3 and H2 (B) Br and CH3Br
(C) Br and CH3OH (D) OH and CH3Br
Ans. (D)
47. KI in acetone, undergoes SN2 reaction with each of P, Q, R and S. The rates of the reaction vary as -
[IIT 2013]
O
Cl
H3C–Cl Cl Cl
P Q R S
(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q
Ans. (B)
ETOOSINDIA N.J. SIR
48. The following reaction, the major product is – [IIT 2015]
CH3 1 equivalent HBr

CH2
H2C
CH3 CH3
CH3 CH2
(A) CH2 (B) H3C
Br
Br
CH3 CH3
(C) H2C Br (D) H 3C

Br
Ans. (D)
Multiple Objective
49. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to-
(A) The formation of less stable carbonium ion [IIT 1990]
(B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbon attached to the halogen
Ans. (B, D)
50. Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with [IIT-1998]
(A) SO2Cl2 /h (B) SOCl2 (C) Cl2 (h) (D) NaOCl
Ans. (A, C)
51. For the following compounds, the correct statement(s) with respect to nucleophilic substitution reactions is(are)
CH3
CH3
Br Br H3C C Br Br
CH3
I II III IV
(A) I and II follow SN2 mechanism [JEE-2017]

(B) Compound IV undergoes inversion of configuration
(C) The order of reactivity for I, III and IV is : IV > I > III
(D) I and III follow SN1 mechanism
Ans. (A,C,D)
ETOOSINDIA N.J. SIR
Match the Column

52. Match the following: [IIT 2006]
Column I Column II
(A) CH3–CHBr–CD3 on treatment with alc. KOH gives (P) E1 reaction
CH2=CH-CD3 as a major product.
(B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q) E2 reaction
(C) Ph-CD2-CH2Br on treatment with C2H5OD/C2H5O– (R) E1cb reaction
gives Ph-CD=CH2 as the major product.
(D) PhCH2CH2Br and PhCD2CH2Br react with same rate. (S) First order reaction
Ans. (A)  Q ; (B)  Q ; (C)  R,S ; (D)  P, S

BKBK

Încărcat de

Informații document

Descriere originală:

Drepturi de autor

Formate disponibile

Partajați acest document

Partajați sau inserați document

Opțiuni de partajare

Vi se pare util acest document?

Este necorespunzător acest conținut?

Drepturi de autor:

Formate disponibile

BKBK

Încărcat de

Drepturi de autor:

Formate disponibile

PREVIOUS YEAR

(3) Cl + KOH (aq)  (4) CH2CH2 Cl + KOH (aq) 

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

10. Consider the following bromides : [AIEEE-2010]

The correct, order of SN1 reactivity is

(a) (b) (c)

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

(1) NaOH/H2O (2) NaOEt/EtOH (3) NaOH/H2O-EtOH (4) NaI

(1) (±) C6H5CH(OtBu)CH2C6H5 (2) C6H5CH=CHC6H5

CH2 CH CH3 CH2 CH2 CH2

(1) C6H5CH C CH 2 CH3 (2) C6H5CH2 C CHCH3

Ans. (i) CH3 C CH CH3 (ii) CH 3 CH 2 CH OH (Unstable), CH3CH2CHO

12. Write the structures of the products : [IIT 1998]

Br2 (i) NaNH2(3 equi.)

15. What would be major product ? [IIT 2000]

CH3 C CH2Br C2H5OH

(i) NaNH2 H2/Pd-BaSO4 alkaline

19. Give reasons : [IIT 2005]

(ii) No reaction takes place, as aryl halide is inert to nucleophilic subsititution.

28. (CH3)3CMgCl reaction with D2O produces : IIT-97]

(A) HO CH2CH3 (B) HO CH2CH2CH3

(C) HO CH2CH3 (D) HO CH3

41. The product of following reaction is [IIT-2003]

(A) C6H5OC2H5 (B) C2H5OC2H5 (C) C6H5OC6H5 (D) C6H5I

(CH3)2NH (i) NaNO2 + HCl 0°–5°C

(A) MeO NO2

(K) MeO NO2

(L) MeO NO2

(M) MeO NO2

45. The major product of the following reaction is [IIT 2008]

H3C SPh H3C SPh H3C SPh

NO2 NO2 NO2

(A) Br OCH3 and H2 (B) Br and CH3Br

(C) Br and CH3OH (D) OH and CH3Br

48. The following reaction, the major product is – [IIT 2015]

CH3 1 equivalent HBr

(C) H2C Br (D) H 3C

(A) I and II follow SN2 mechanism [JEE-2017]

Match the Column

S-ar putea să vă placă și