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Haloalkanes and Haloarenes Class 12 Motion
Haloalkanes and Haloarenes Class 12 Motion
Haloalkanes and Haloarenes Class 12 Motion
COOAg
10. In Finkelstein Reaction, which reactants are used -
(C) (D) (A) NaI + C2H5OH (B) NaCl + acetone
Br (C) NaBr + CH3COCH3 (D) NaI + CH3COCH3
(
O)
CH3CHO, Identify A, B & C -
15. The rate law for the reaction, RCl + Na (a)
ROH + NaCl is given by, rate = K1 [RCl]. The (A) Ethylalcohol Ethyl chloride & Ethane
rate of the reaction will be - (B) Ethane, Ethylchloride & CH3–CH2–OH
(C) Propane, Propylchloride & CH3–CH2–CH2–OH
(A) Doubled on doubling the concentration of so-
(D) All the above
dium hydroxide
(B) Halved on reducing the concentration of alkyl
21. An alkyl halide reacted with a metal cyanide to give
halide to half
an alkanenitrile. The metal cyanide is -
(C) Decreased on increasing the temperature of
(A) AgCN (B) KCN
the reaction (C) Cu2(CN)2 (D) Ba(CN)2
(D) Unaffected by increasing the temperature of
the reaction 22. A strong solution of alcoholic alkali will preferen-
tially promote alkyl halide into an alkene by
16. Chlorobenzene is - (A) Addition (B) Elimination
(A) More reactive than ethyl bromide (C) Polymerisation (D) Substitution
(B) More reactive than isopropyl chloride
(C) As reactive as methyl chloride 23. When ethyl bromide is treated with moist Ag2O the
(D) Less reactive than benzyl chloride product is -
(A) Ethyl ether (B) Ethanol
17. Vinylic halides are unreactive towards nucleophilic (C) Ethoxy ethane (D) All of the above
substitution because of the following except -
(A) C - halogen bond is strong 24 A carbon compound A forms B with sodium metal
(B) The halogen is bonded to sp2 carbon and again A forms C with PCl5 but B and C form
diethylether. Therefore A, B & C are -
(C) A double bond character is developed in the
(A) C2H5OH, C2H5 ONa, C2H5Cl
carbon-halogen bond by reasonance
(B) C2H5Cl, C2H5 ONa, C2H5 OH
(D) Halide ions are not good leaving groups
(C) C2H5OH, C2H6, C2H5Cl
(D) C2H5OH, C2H5 Cl, C2H5ONa
18. When an alkyl halide reacts with an alkoxide, the
product is- 25. Action of alcoholic AgNO3 on chlorobenzene is
(A) Ether (B) Ester similar to the action on -
(C) Hydrocarbon (D) Alcohol (A) Allyl chloride (B) Vinyl chloride
(C) Isopropyl chloride (D) Benzyl chloride
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Alkyl halide | 3
26. The number of steps involved in SN1 and SN 2 32. Reaction of ethyl bromide and silver acetate gives –
mechanisms are given by the set - (A) Ethyl ethanoate
(A) 1,2 (B) 3,1 (B) Methyl ethanoate
(C) 2,1 (D) 2,2 (C) Ethanoic anhydride
(D) 2-Butanone
39. Which of the following statement is wrong - 47. Pyrene is the commerical name of -
(A) All carbonyl compounds of the general struc- (A) Degreasing agent CHCl3
ture CH3–C–R give a positive iodoform test (B) Fire extinguisher CCl4
O (C) Insecticide CHI3
(B) All secondary alcohols give iodoform reaction (D) Aerosol, propellant, C2Cl4 F2
(C) Alkanols of the structure CH3CH(OH) - R (where
R=H, alkyl or aryl) give iodoform reaction. Physical properties and test of Alkyl halide
(D) The only aldehyde giving iodoform reaction is 48. The yield of alkyl bromide obtained as a result of
acetaldehyde. heating the dry silver salt of carboxyic acid with
bromine what will be the order of formation w.r.t.
40. The oxidation of CHCl3 by air & light is prevented alkyl bromide -
by adding - (A) 1º > 3º > 2º bromides
(A) CH3COOH (B) C2H5OH (B) 1º > 2º > 3º bromides
(C) CH3CHO (D) CH3COOCH3 (C) 3º > 2º > 1º bromides
(D) 3º > 1º > 2º bromides
41. Isocyanide reaction involves the intermediate for-
mation of -
49. True about alkyl halides is/are -
(A) :CCl2 (B) CH3+
(A) Tertiary alkyl halides undergo SN2 substitutions
(C) CH3¯ (D) CCl3
(B) Alkyl iodides on exposure to sunlight gradually
42. Chloroform when treated with aniline and alcoholic darken
KOH forms - (C) Alkyl chlorides do not give beilstein test
(A) Phenyl cyanide (B) Phenyl isocyanide (D) A nucleophilic substitution is most difficult in
(C) Phenyl cyanate (D) Phenyl isocyanate alkyl iodides
43. Iodoform test is not given by : - 50. The correct order of density is -
(A) C6H5COC6H5 (B) CH3COCH3 (A) C2H5I > C2H5Br > C2H5Cl
(C) CH3CH2COCH3 (D) CH3CH2CHOHCH3 (B) C2H5 > C2H5Br > C2H5I
(C) C2H5Cl > C2H5I > C2H5CBr
44. The compound with no dipole moment is - (D) None of these
(A) Methyl chloride
(B) Carbon tetrachloride
51. Ethyl bromide and isopropyl chloride can be
(C) Methylene chloride
distinguished by -
(D) Chloroform
(A) Alcoholic AgNO3
(B) Comparing their colours
45. The hydrogen atom in chloroform is -
(C) Burning the compounds on spatula
(A) Acidic (B) Basic
(C) Neutral (D) None of these (D) Aqueous KOH solution
46. Iodoform gives a precipitate with AgNO3 on heating 52. The compound C2H4Cl2 has two isomers and they
but chloroform does not because - can be distinguished by the reaction with
(A) Iodoform is ionic (A) Aq. KOH (B) Alc. KOH
(B) Chloroform is covalent (C) Bromine water (D) NaNH2
(C) C–I bond in iodoform is weak and C–Cl bond
in chloroform is strong
(D) None
O Br
2. product are
Ph — C — CH3 PCl5
(C) Br
Cl
| Br
(A) Ph — C — CH3 (B) Ph — CH — CH 2 (D) Br
| | |
Cl Cl Cl
Cl CH3
(C) Ph — CH 2 — CH Zn—dust
H Br
Cl 6. (p). The product (p)
Br H
(D) Ph — CH2 — CH2 — Cl
CH3
3. In the acid catalyzed dehydration of alcohols to
alkenes, the intermediate species formed is is
(A) Free radical
(B) Carbocation (A) (B)
(C) Carbanion
(D) Carbene
(C) (D)
Br
H3C H
4. Anti elimination ? major 7. Which of the following compound will be most
—Br2 reactive for SN1 and SN2 reactions
H CH 3
Br
products is : I Cl
H3C H
O O
(A) (A) (B)
H CH 3
H3C H Cl
Br
(B)
O
H3C H (C) (D)
O
(C) both (A) & (B) (D) none of these
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6 | Alkyl halide
CH3 CH 3 Br
Zn
11. + ZnBr2
8.
Br
Cl
This reaction is a case of
Total number of SN1 products of given compound (A) -elimination (B) -elimination
are
(C) -elimination (D) none of these
(A) 3 (B) 4
(C) 5 (D) 6
Br
SN2 12.
Nu + C [TS] C + L
9.
Which of the following figures represent correctly The major products obtained when this substrate is
the structure of transition state in this reaction? subjected to E2 reaction will be
C
(A) [ Nu (A) (B)
alc. KOH
17. CH 3 — CH2 — CH — CH 3
CH3
Br
15.
X EtONa
;
Br Major CH 3 — CH2 — CH — CH 3
CH3 NMe3
+
Y
The major product obtained when this substrate is Major
subjected to E2 reaction will be
Product (X) and (Y) respectively is
(A) 1-butene, trans-2-butene
CH3 CH2
(B) 1-butene, cis-2-butene
(A) (B)
(C) cis-2-butene, 1-butene
(D) trans-2-butene, 1-butene
CH3 CH3
CH 3
Br
16. If the following E2 reaction proceeds through an CH3
anti-periplaner transition state, what products are
expected ? The major product obtained when this substrate is
CH 3
subjected to E1 reaction will be
CH 3 CH3
Cl
(A) (B)
(A) Only 3-methylcyclohexene
(B) Only 1-methylcyclohexene CH2 CH3
(C) The major product is 3-methylcyclohexene and
the minor product is 1-methyl cyclohexene CH 3
(D) The major products is 1-methylcyclohexene and (C) (D) none of these
the minor product is 3-methyl cyclohexene
CH3
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8 | Alkyl halide
CH3 +
H
(A) (B)
CH2OH
9. (i) (A) Major
OH
CH2OH CH3
| |
OH +
(C) (D) H
(ii) (B) Major
OH
7. SN1 & SN2 product are same in (excluding steroisomer)
Cl OH
H
+
H
(A) (B) (C) Major
Cl
Cl
10. Which alcohol is most reactive towards dehydration 14. Reaction Reaction rate of reaction
of alcohols in acids catayzed reaction. (A) HO + R — CH2 — I (P) 1
(B) HO + R — CH2 — Br (Q) 200
OH OH
(C) HO + R — CH 2 — Cl (R) 10,000
(D) HO + R — CH2 — F (S) 30,000
(A) (B)
15. column I Column II
Alkyl-bromide Relative rate of SN1
CH3
OH |
(A) CH3 — C — Br (P) 1
OH |
CH3
(C) (D) (B) CH 3 — CH — Br (Q) 11.6
|
CH3
(C) CH3 — CH2 — Br (R) 1,200,000
Matrix Match
11. Column I Column II 16. column I Column II
Primary alkyl bromide SN2 relative rate Solvent Relative rate of SN1
(A) CH3 — CH2 — Br (P) 10–5 (A) 100% water (P) 1200
(B) Me — CH2 — CH2 — Br (Q) 10–2 (B) 80% water + 20% ethanol (Q) 400
(C) 50% water + 50% ethanol (R) 60
(C) Me — CH — CH 2 — Br (R) 0.8
| (D) 20% water + 80% ethanol (S) 10
Me (E) 100% ethanol (T) 1
Me
|
(D) Me — C — CH2 — Br (S) 1 17. Match List-I with List II for given SN2 reaction &
| select the correct answer from the codes given
Me
below
12.
Z—CH 2Br + CH 3O Z—CH 2OCH3 + Br
Column I Column II
Alkyl—P—toluene sulfonate Ethanolysis relative List I List II (relative reactivity)
(A) CH3 — CH2 — OTs (P)1010 (A) H— (P) 0.1
(B) H2C = CH — CH2 — OTs (Q) 105 (B) CH3— (Q) 3
(C) Ph — CH2 — OTs. (R) 400 (C) C2H5— (R) 1
(D) Ph — CH — OTs (S) 35 CH 3
| (D) CH— (S) 100
Ph
CH3
(E) Ph3C — OTs. (T) 1
13.
Substrate E2 elimination SN2 — substitution
(A) CH3 – CH2 – Br (P) 1 (W) 0
(B) (CH3)2CH – Br (Q) 80 (X) 20
(C) (CH3)3CBr (R) 100 (Y) 90
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10 | Alkyl halide
(A)
H PhCl
– CH – C – CH3 PhS Cl
O
OEt
(D)
Cl
CH3 CH3
(B) Ph H
– C — CH — CH3 H
(C) (D)
Br OEt
Br Br Cl
3. Ph CH3
(C) OCH3
II III CH3 (x) conc.
CH3 HI
I
7.
OCH 3
SN2 reactivity of these substrate, under identical OEt CH3
conditions, will be in the order as Value of x in above reaction is
(D) Ph – C — C — CH3
(A) I > II > III (B) III > II > I (A) 2 (B) 3
H CH3
(C) III > I > II (D) II > III > I (C) 4 (D) 5
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Alkyl halide | 11
CH3
SOCl2
11. H OH (A) . Product (A) in
Et
CH3 Et
(A) H Cl (B) H Cl
Et CH3
CH 3
(C) Cl H (D)
Et
H 3O
12. CH3 – CH 2 – O – C = CH2 Products
CH 3
are
O
(A) + EtOH
O
(B) + EtOH
OH
(C) + EtOH
OH
(D) + O
H3O
excess X
13.
O O
Structure of X is
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12 | Alkyl halide
Br Br
(B) O
OH H O OH
(III)
Br
(C)
OH (A) III > I > II (B) III > II > I
O OH
(C) II > III > I (D) II > I > III
CH2 — OH
(D) (x)HBr
HO HO HO 16.
OH
OTs S
| |
(A) CH3 — CH — CH2 — CH2 — CH — CH3
Cl OCH3
OCH3 Cl
(C) (D) S S
| |
O Cl O Cl (B) CH3 — CH — CH2 — CH2 — CH — CH3
S
CH3 CH3
(C) (C) t-Bu
CH3 CH3
(D) t-Bu
(D) S OAc
Br
| (x) NaNH2 +
20. Ph — CH — CH 2
O |
Br (x = No. of moles of NaNH2)
+
H
18. (B) , Give structure of (B) Value of x is
(A) 1 (B) 2
O (C) 3 (D) 4
+
H
CH3 — CH — CH3 CH3 — CH — CH3
| +|
OH O
(C) (D) H H
+ +
O —H
CH3 — CH — CH3 CH3 — CH = CH2
t-Bu +
OTs AcO Na
19. (A)
(A) E (B) E
Major-product (A) is
rxn-coordinate rxn-coordinate
(A) t-Bu
OAc
(C) E (D)
E
OAc
rxn-coordinate
(B) t-Bu rxn-coordinate
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14 | Alkyl halide
CH3 OH
O
+
CH 3 H
22. (x)
OH (C) (D)
(P) (Q)
(C) (D)
OH
(A) (B)
OH (A) P > Q > R > S (B) Q > P > R > S
(C) R > Q > P > S (D) R > Q > S > P
(C) (D)
OH OH
26. HO OH
OH
OH conc. H2SO4
A
H2SO4
24. X, X is Final product A is
(A) HO O
(C)
(A) (B) O
(D) HO
O
Me Me
(A) (B)
Me Me
O CH3
Br
Me 31. CH3
Me
(C) (D) Me
C—Me
O
O
The major products obtained when this substrate to
Me E2 reaction under the treatment of potassium tert-
H Et alc. KOH butoxide will be
28. major product is :
Br Et
Me CH2 CH3
Me Me
(A) (A) (B)
Et Et CH3 CH3
Me Me
CH 3 CH3
H Et H Et
(C) (D) 32. I II
Me Br
Br
CH3
OEt III
(A) (B) OEt
OEt Br
Br
be in the order as
| (A) i > ii > iii (B) iii > ii > i
30. —C — CH2 — CH3
| (C) ii > i > iii (D) ii > iii > i
CH2 — CH2 — CH3
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16 | Alkyl halide
CH3OH Cl
33. CH3O — CH = CH2 product formed is
H+
Cl Cl
(A) Acetal (B) Hemiacetal (C)
(C) Alcohol (D) aldehyde
Cl Cl
Cl
Br
(D) all three are equally reactive
34. CH3 — CH2 — CH2 — C — CH2 — CH3
CH3
37. The nitrogen atom in each of the following tertiary
Total number of SN1 + E1 products obtained will be - amines may be removed as trimethyl amine by
(A) 5 (B) 6 (C) 7 (D) 8 repeated Hofmann eliminations (exhaustive
methylation followed by heating with AgOH).
Which of the amines requires the greater number
CH3
+ of Hofmann sequences to accomplish this ?
35. CH3 — C — CH2 — CH3 H
CH3 OH CH3
N
(A) (B)
N
+
(A) H
N(CH3)2 CH3
OH N
(C) (D)
OH +
(B) H (C)
Br CH3
– SN2
38. + OH A , A is
H H
Stability of product (A), (B), (C) is :
(A) C > B > A (B) A > B > C
HO H
(C) B > C > A (D) C > A > B
(A)
H CH3
36. Which of the following isomeric
hexchlorocyclohexanes is least reactive in ( )-
H CH 3
dehydrochlorination of treatment with strong base (B)
OH H
Cl Cl
Cl Cl Cl Cl
(A) (B)
HO CH 3
Cl Cl Cl Cl (C) both (D)
H H
Cl
Cl
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Alkyl halide | 17
18
O—CH3 Ph Ph
Conc. HI
39. Product are C=C
(A)
18 MeO CH3
OH I
18 Ph Ph
(A) + CH3I (B) + CH3OH
(B) MeO C– C=O
OH I
CH3
(C) + CH3I (D) + H2O
Ph
(A) (B)
(i) OH (ii) OH
OMe
(iii) OH (iv) OH
(A) i < ii < iii < iv (B) ii < iii < iv < i 43. Which of the following expressions is the
(C) i < iii < iv < ii (D) i < ii < iii = iv
experimentally observed rate law for an E2 reaction
of alkyl halide ?
Ph Ph (A) Rate = k[RX]
C—C
(B) Rate = k [RX]2
42. OH OH
(C) Rate = k[RX][base]
MeO CH3
(D)Rate = k[base]
Conc. H2SO4
A, A is :
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18 | Alkyl halide
14. A solution of (–) –1–chloro–1-phenylethane in 19. Which of the following, upon treatment with tert-
toluene racemizes slowly in the presence of a small BuONa followed by addition of bromine water, fails
amount of SbCl5. due to formation of : to decolourize the colour of bromine ?
[JEE Main 2013] [JEE Main 2017]
(A) carbocation (B) free radical O
C6H 5
(C) carbanion (D) carbene
(A) (B)
15. In SN2 reactions, the correct order of reactivity for Br Br
the following compounds ? [JEE Main 2014] O
CH3Cl, CH3CH2Cl, (CH3)2CHCl and (CH3)3CCl is O
(A) CH3CH2Cl > CH3Cl > (CH3)2CHCl > (CH3)3CCl (C) (D)
(B) (CH3)2CHCl > CH3CH2Cl > CH3Cl > (CH3)3CCl Br
Br
(C) CH3Cl > (CH3)2CHCl > CH3CH2Cl > (CH3)3CCl
(D) CH3Cl> CH3CH2Cl > (CH3)2CHCl > (CH3)3CCl
20. The major product formed in the following reaction
16. The synthesis of alkyl fluorides is best accomplished is: [JEE Main 2018]
by : [JEE Main 2015]
(A) Free radical fluorination
(B) Sandmeyer's reaction
(C) Finkelstein reaction
(D) Swarts reaction
(A) (B)
NO2
F F
(A) (B)
H , (i) O3
4. X
Y.
(ii) Zn / CH3COOH
NO2 NO2
Identify X and Y. [IIT 2005]
Me Br Me SPh O
C
SPh SPh
(A) N—CH2 Br
(C) (D)
C
O
NO2 NO2
O
C
9. The correct stability order for the following species
is [IIT ‘2008] (B) N CH 2Cl
C
O O
(I) (II)
O
C
O
(III) (IV) (C) N
(A) II > IV > I > III (B) I > II > III > IV C
(C) II > I > IV > III (D) I > III > II > IV
O — CH2 Br
11. The synthesis of 3-octyne is achieved by adding a 14. The total number of alkenes possible
bromoalkane into a mixture of sodium amide and by dehydrobromination of 3-bromo-3-
an alkyne. The bromoalkane and alkyne cyclopentylhexane using alcoholic KOH is :
respectively are – [IIT 2010] [IIT 2011]
(A) BrCH 2CH2CH2CH2CH3 and CH3CH2CCH
(B) BrCH2CH2CH3 and CH3CH2CH2CCH 15. The major product of the following reaction is
(C) BrCH2CH2CH2CH2CH3 and CH3CCH
(D) BrCH2CH2CH2CH3 and CH3CH2CCH RCH2OH
+ [IIT 2011]
1]
H (anhydrous)
12. The bond energy (in kcal mol–1) of a C – C single O
bond is approximately [IIT 2010] (A) a hemiacetal (B) an acetal
(A) 1 (B) 10 (C) an ether (D) an ester
(C) 100 (D) 1000
16. KI in acetone, undergoes SN2 reaction with each
13. The major product of the following reaction is : of P,Q,R and S. The rates of the reaction vary as.
O [IIT 2011] [JEE Adv. 2013]
C O
(i) KOH
NH Cl
H3C—Cl Cl
C
(ii) Br CH 2Cl (A) P>Q>R>S (B) S>P>R>Q
O (C) P>R>Q>S (D) R>P>S>Q
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22 | Alkyl halide
(C)
Me OH
The observed pattern of electrophilic substitution
can be explaind by :
(A) the steric effect of the halogen
(B) the steric effect of the tert-butyl group (D)
Me OH
(C) the electronic effect of the phenolic group
(D) the electronic effect of the tert-butyl group
21. LIST-I contains reactions and LIST-II contains
18. In the following monobromination reaction, the major products. [JEE Adv. 2018]
number of possible chiral products is: LIST-I
[JEE Adv. 2016]
CH2CH2CH3 P. +
Br2(1.0 mole) ONa Br
H Br
CH3 300°C
(1.0 mole) Q. + HBr
(enantiomerically pure) OMe
R. + NaOMe
19. For the following compounds, the correct Br
statement(s) with respect to nucleophilic substitution
reactions is (are) [JEE Adv. 2017]
S. + MeBr
ONa
Br Br
LIST-II
(I) (II)
1.
CH 3 CH3 OH
H 3C—C—Br Br
2.
CH 3 Br
(III) (IV)
(A) I and II follow SN2 mechanism 3.
(B) Compound IV undergoes iniversion of configuration OMe
(C) The order of reactivity for I, III and IV is : IV 4.
> I > III
(D) I and III follows SN1 mechanism O
5.
20. In the following reaction sequence, the correct Match each reaction in LIST-I with one or more
structure(s) of X is (are) [JEE Adv. 2018] product in LIST-Il and choose the correct option.
Me N3 (A) P 1, 5; Q 2; R 3; S 4
(1) PBr3, Et2O
X (B) P 1, 4; Q 2; R 4; S 3
(2) NaI, Me2CO
(3) NaN3, HCONMe2 (C) P 1, 4; Q 1, 2; R 3, 4; S 4
enantiomerically pure (D) P 4, 5; Q 4; R 4; S 3, 4
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Alkyl halide | 23
22. Choose the correct option(s) for the following set of reactions [JEE Adv. 2019]
(A) (B)
S U U T
(C) (D)
S T U S
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24 | Alkyl halide
1. D 2. D 3. C 4. A 5. B 6. C 7. C
8. B 9. C 10. D 11. B 12. D 13. B 14. C.
15. B 16. D 17. D 18. A 19. A 20. B 21. B
22. B 23. B 24. A 25. B 26. C 27. B 28. A
29. B 30. C 31. A 32. A 33. C 34. A 35. D
36. B 37. D 38. A 39. B 40. B 41. A 42. B
43. A 44. B 45. A 46. C 47. B 48. B 49. B
50. A 51. A 52. A
1. A 2. D 3. A 4. A 5. (B, D) 6. (A,B) 7. B, C
8. D 9. D 10. A
11. A S ; B R ; C Q ; D P 12. A T ; B S ; C R ; D Q; E P
13. A P, Y ; B Q, X ; C R, W 14. A S ; B R ; C Q ; D P
15. A R ; B Q ; C P ; 16. A P ; B Q ; C R ; D S; E T
17. A S ; B Q ; C R ; D P
1. A 2. B 3. B 4. C 5. A 6. A 7. A
8. C 9. C 10. B 11. A 12. A 13. B 14. A
15. A 16. A 17. C 18. B 19. B 20. C 21. C
22. A 23. A 24. D 25. C 26. C 27. D 28. B
29. A 30. C 31. A 32. D 33. A 34. C 35. D
36. B 37. A 38. C 39. A 40. A 41. A 42. B
43. C
SbCl5
CH – CH3 CH – CH3
Lewis acid
Carbocation
Cl
15. D
SN2
1. A 2. A 3. D
O
4. (x) (y)
CH3–C–(CH2)4–CHO
CH3
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