Exercise 1 1686225084

JEE (MAIN + ADVANCED) : ENTHUSIAST COURSE
SUBJECT : ORGANIC CHEMISTRY

Topic : HALOGEN DERIVATIVE Exercise : O-1
1. HD0001
Ans. (A)
O
Sol. CO2 ® contain polar C
CH 3Å ® vacant p-orbital
CH2 ® Octet incomplete
®
Br2 ® instantaneous dipole formation
So option (A) contain all electrophile
2. HD0002
Ans. (C)
Sol. In case of option (C) either the compound is having lone pair (–OH, – NH2) or pe density
( CH2 = CH2 ) thus all are nucleophiles
®
3. HD0003
Ans. (D)
Å
Sol. (A) H+ (3° carbocation)
H CH3
®
Å
(B) H
+
(3° carbocation)
H+ Å
(C) CH2 CH2 (3° carbocation)
NH2 H+ Å NH2
(D) (Back bonding 2° carbocation)
4. HD0004
Ans. (D)
Sol. Carbocation
(i) It has vacant orbital thus can act as Lewis acid
(ii) It has 6 valence shell e–
(iii) It is electrophile
(iv) It is always trigonal planar
Option (D) is incorrect as always trigonal planar is not necessary
®
5. HD0005
Ans. (C)
CH3
Sol. C CH3
Å
HO
This is the most stable carbocation due to resonance i.e. Back Bonding
®
6. HD0006
Ans. (C)
Å
Sol. the above carbocation cannot be formed as it violates BREDT’S RULE
®
7. HD0007
Ans. (B)
CH3 CH3
Å
Sol. (A) (Stability decreases)
Å
(4aH) (3aH)
®
CH3 CH3
Å Å
(B) (Stability increases)
(3aH) (7aH)
Å
Å
(C) (Constant)
(4aH) (4aH)
CH3 CH3
(D) Å Å
(Decreases)
8. HD0008
Ans. (D)
Sol. Å
Å
1, 2 shift
1, 2 shift
®
Å
1 shift
Å
1, 2 shift
Å So we can see total

no. of 1, 2 shift are 4
9. HD0009
Ans. (B)
Sol. In case of (a), (b), (c), (d), (e), (f), (g), (h)
In all cases stability of carbocation increases after rearrangment
®
10. HD0010
Ans. (B)
Sol. (A) Cl Å DH1

0
Å DH2
0
(B) Cl
®
Å
CH2 DH3
0
(C) CH2Cl
Å DH4
0
(D) Cl
DHº depends upon the stalibility of carbocation, more stable CÅ less DHº
thus DH o4 > DH1o > DH o2 > DH 3o
11. HD0011
Ans. (C)
Br Å + Br
(I) (Aromatic
®
Sol. compound)
Br Bromo cyclo Propane
(I) is having higher dipole moment due to formation of complete positive charge.
12. HD0012
Ans. (C)
Sol. Racemisation occurs when carbocation is formed as an intermediate
®
13. HD0013
Ans. (C)
OH
Conc. H2SO4
®
OH
Å Å
+
H 1, 2 shift
Sol.
ring (1, 2 shift) Å (1, 2 shift) Å

Expansion
So we can say 3 Þ 1, 2-shifts

14. HD0014
Ans. (A)
CH3 CH3
Sol. +
CH3 H CH3
D Å –H2O
OH OH2
CH3 CH3
®
CH3 1, 2 shift Å
D
Å
CH3
CH3
(Major Product)
CH3
15. HD0015
Ans. (D)
Sol. Å
OH OH2
H+
Å
–H2O 1, 2 shift
OH
®
Å
H2O
5ºC
No elimination as heat is not given

16. HD0016
Ans. (B)
Sol.
+ Å
H
D
®
OH
Å
1, 2 shift D
ring expansion
17. HD0017
Ans. (A)
Sol. Correct order of Dehydration
(I) OH Not possible
H+
(II) OH Å (Hyper)
®
H+
(III) OH Å (Reso)
H+
(IV) OH Å (More Reso)
Rate Þ IV > III > II > I

18. H D0018
A ns. (D)
Sol. OH OH OH
H+
D Å
Me Me Me Me
®
Me
OH Å
1, 2 shift
HO Å Me
Me
Me
D
Me
HO Me
19. HD0019
Ans. (C)
CHÅ Å CH3
2
Sol. (P) Reso (Q) Reso + 2 a H
Å CH3
Å CH3
Reso + 5 a H 3aH
®
(R) (S)
(R) > (Q) > (P) > (S)

20. H D0020
A ns. (D)
OH OH OH OH
+ Å Å
H 1, 2 shift D
Sol.
O OH OH OH
®
21. HD0021
Ans. (D)
Sol. Å
OH OH2
+ Å
H
®
Å
Ring-exp.
Å Ring-exp.
H
+
–H
(Major)
22. HD0022
Ans. (A)
OH
Sol. Ph — C º C — CH — Ph
+
H Å
®
OH2
–H2O Å
Ph — C º C — CH — Ph Ph — C º C — CH — Ph
(R.D.S.)
Å
OH2
O
H H Å
Ph — C = C = CH — Ph Ph — C = C = CH — Ph
+
–H
OH
Ph — C = C = CH — Ph
tautomerisation
O
Ph — C — CH = CH — Ph
23. HD0023
Ans. (D)
Sol. Given reaction is an example of SN1.
So rate of SN1 µ stability of Ist formed carbocation.
Stability of carbocation will be-
Å Å Å Å
CH2 CH2 CH2 CH2
®
> > >
O – CH3 Cl NO2
So rate of reaction with HBr will be-
CH2– OH CH2– OH CH2– OH CH2 – OH
> > >
O – CH3 Cl NO2
24. H D0024
A ns. (A )
Sol. Rate of dehydration µ stability of Ist formed carbocation.
OH
H+ Å
(a) C—C—C—C C—C—C—C
C C
®
OH
H+ Å
(b) C—C—C—C C—C—C—C
C C
(c) H
+
Å
C — C — C — C — OH C—C—C—C
H+ Å
(d) C — C — C — C — OH C—C—C—C
C C
So according to stability of carbocation (a) give fastest rate of dehydration reaction.
25. HD0025
Ans. (B)
Sol. "b" is most reactive because after attacking of electrophile on double bond (b). Formed carbocation
intermediate is stablised by maximum resonance-
e
e
+
®
O O
26. HD0026
Ans. (C)
Å
OH OH2
Sol. Å
H+ –H2O
D
®
1,2-shift
–H+ Å
(Major)
27. HD0027
Ans. (B)
Sol. Pinacol-Pinacolone reaction is an example of intramolecular reaction.
So in given reaction only two products are formed.
Et Ph Me Ph O Ph O Ph
H /D
+
HO OH + HO OH Et — C — C — Ph + Me — C Ph
®
Et Ph Me Ph Et Me
28. HD0028
Ans. (C)
Sol. Rate f Pinacol-Pinacolone µ stability of formed carbocation
So stability of carbocation is-
Me Ph Me Me Me Me
HO Å Ph > HO Å Ph > HO Å Me
®
Me Ph Me
29. HD0029
Ans. (D)
Me Me
Sol. +
H
Me D
Me
OH OH OH OH2
Å
®
30. H D0030
A ns. (B)
Sol. Reactivity of Alkene with H – Br explained by two factor
(1) by stability of formed Carbocation
(2) by nucleophilicity of Alkene
By both concept reactivity will be-
> >
Me – O MeO
®
31. H D0031
A ns. (D)
Å Å
Å
HBr
Sol. (A) Expansion Shifting
®
Br –
Br
HBr Å Br
– Br
(B)
H – Br Å Br– Br
(C)
H H
(D) H – Br Å Br– Br
32. HD0032
Ans. (B)
OH O–H
Sol. H
+
O R.D.S O Å
Internal
attack
®
H
Å
O –H
+
O
O O
33. HD0033
Ans. (B)
Sol. Reactivity of alkene for electrophilic addition reaction µ nucleophilicity of Alkene
O Me Cl
Nu– of Alkene: > >
®
34. HD0034
Ans. (C)
50%
Et Et Et Et
Å
C = CH2 C — CH3 Br Me Me Br
HBr Br–
H CCl4 H +
Sol. D D H D H D
Me Me Me Me
®
50%
Note: On classical carbocation nucleophile attack 50% from front side and 50% from back side
35. HD0035
Ans. (A)
OH
H3O+
Sol. (P)
®
OH
H.B.O (Q)
OH
O.M.D.M. (R)
P & R are same

36. HD0036
Ans. (A)
Me Me
CCl4 H Br Br H
+ Br2 +
H Br Br H
Sol. Et Et
®
Enantiomers
Note: Meso is not formed because Alkene is unsymmetrical
Product is Active but product mixture is inactive due to Racemisation

37. HD0037
Ans. (C)
H +
Formed (C )
Sol. H – Br H – Br
stablised
(R.D.S)
Å by resonance CH3 – I
N N N· · NÅ
1
(SN )
–
Br
®
Br Å
–
Br
N Br NÅ NÅ
38. HD0038
Ans. (D)
H
Sol. N
®
Br – Br
H H
Å
N N N
–H+
Br
Å Br Br
39. HD0039
Ans. (A)
Cl
Cl
CH3 – OH
Sol.
O Cl
Weak nucleophile as well as polar-protic solvent (CH3–OH) both favour SN1 reaction and SN1 reaction
®
rate µ stability of formed carbocation
Cl Cl Cl
Cl Cl Cl
CH3– OH
–
– Cl
Å O CH3
O Cl O O
stabilised by resonance
40. HD0040
Ans. (B)
Sol. Rate of SN1 µ stability of formed carbocation
CH3
Å
most stable carbocation
®
41. HD0041
Ans. (B)
Sol. The reactivity for hydrolysis µ stability of carbocation.
Å Å
CH2 H — C — C2H5
(i) (ii)
®
Only Resonance Stable due to resonance
and +I and Hyperconjugation
CH3
Å
(iii) (iv) +
C
H
least stable Most stable due to
antiaromatic dancing resonance
So, decreasing order of stability IV > II > I > III
So, decreasing order of reactivity IV > II > I > III
42. HD0042
Ans. (C)
Sol. Reactivity towards SN1 µ stability of carbocation
stability of carbocation µ + R / + H / + I
Å Å
CH2 CH2
(A) (B)
®
CH3
Å Å
CH2 CH2
(C) (D)
OCH3
·
· NO2
Most stable due Least stable due to
to +R of ·· O — CH3 – R of –NO2
·
·
·
·
CH2 — Cl
So, most reactive is
OCH3
43. HD0043
Ans. (A)
Sol. Rate SN1 µ stability of carbocation
Å Å
CH2 CH2
(I) least stable, No a – H (II) ® most stable, 3a – H
®
CH3 Å
Å CH2
CH2
(III) 2a – H (IV) 1a – H
H3C — C — CH3
CH2 — CH3
H
44. HD0044
Ans. (C)
Sol. treatment with HOH proceeds Via SN1 and carbocation is formed as intermediate, so the attacking
reagent attack over positive charge (Planar) carbon from both the side and gives enantiomeric pair if
compound has at least one chiral center.
H
So, H5C6 — C — Br ¾¾¾
HOH
® Enantiomeric pair
®
D
45. HD0045
Ans. (A)
Sol. Reactivity towards Solvolysis in aqueous medium µ stability of carbocation
H3C Å
(i) C — C — CH3
H3C
H H least stable
CH3
Å
®
(ii)
Å
(iii) H5C6 — C — C 6H5 most stable decreasing order of stability III > IV > II > I
H
Å
(iv)
46. HD0046
Ans. (C)
Sol. Most stable carbocation gives maximum racemisation if they have three different valencies.
Å
H5C6 C O CH3 ® +R
®
Most stable
CH3
+H
47. HD0047
Ans. (D)
Me
H Me
C Br2 H Br
CCl4 H Br
C
Me H
Sol. Me
®
[P]
(i) Meso
(ii) POS is present
[P] have three optical isomer.

48. HD0048
Ans. (D)
Sol. Ease of hydrolysis of alkyl halide µ stability of carbocation
O
–R
(I) um
(II)
R maxim
–I – O +R
+ O +
®
O um
– Im axim
–R,
(III) (IV)
O –I
O
·
·
·
·
+ +R
49. H D0049
A ns. (B)
D D HI
1
Sol. OH SN
H
H
®
+
–H2O H
D OH +
–
C
1-2 D
shift
D C–D
Å H2
CH2
ring expansion
D D
I –
I +
CH2 C—D
D H2
50. H D0050
A ns. (C)
3
CH3
HOH
Sol. 4 H I 1 Product 96% racemisation
Et
2
®
S So,
48% 52%
SN 1
SN 2
Retention inversion
So, Among the product 48%S configuration and 52% R configuration
51. HD0051
Ans. (B)
Sol. H3C — C = C — CH2 — OH
H H
+
–H2O H
®
+
H3C — C = C — CH2
H H
Br
+ Br –
H3C — C — C = CH2 H3C — C — C = CH2

H H H H
More stable [P]
52. HD0052
Ans. (C)
Br
+
–
+ Br
least stable
(Anti Aromatic)
®
53. HD0053
Ans. (A)
I
Sol. (A) O is most reactive towards SN1
Because I– is better leaving group so easily gives carbocation and that is more stable due to resonance
+
®
O ··
·
·
(pp – pp) or backbonding.

54. HD0054
Ans. (C)
Cl
SN1 +
C C + Cl
®
Most stable
55. HD0055
Ans. (A)
O
(I) (II) (III)
®
Br Br Br
–Br –Br
+Br O
Sol.
+ +
+
Non-aromatic Antiaromatic Aromatic

least stable most stable
Order of reactivity towards SN1 µ stability of C+

So. III > I > II
56. HD0056
Ans. (D)
Sol. In SN2 the reaction intermediate is Transition state, that has partial carbocation character.
The stability of carbanion is ® – R/ – H/ – I
CH2– Cl
®
NO2(–R)
57. HD0057
Ans. (C)
Sol. Br– + H3C – OH ¾¾®
SN 2 Br – CH3 + OH
For SN2, Rate = k[CH3Br] [ OH ]
®
58. HD0058
Ans. (B)
Sol. SN reaction takes place when nucleophile is more basic than leaving group.
Nu L.G.
Br + CH3 – OH Br – CH3 + OH
Weak Strong
base Base
so reaction will not take place
®
59. HD0059
Ans. (B)
Sol. In SN2 nucleophile approch from the back side over carbon
Br CH3 2 H CH3
– SN
HO + Br
H H OH H
®
60. HD0060
Ans. (C)
(I) 2-bromo-2-methyl butane
Br
H3C — C — CH2 — CH3 3°
CH3
(II) 1-Bromopentane
®
H3C – CH2 – CH2– CH2 – CH2 – Br ® 1°
(III) 2-Bromopentane
Br
H3C — C — CH2 — CH2 — CH3 2°
H
Reactivity order of Alkyl halide towards SN2 ® 1° > 2° > 3°
So, II > III > I
61. HD0061
Ans. (C)
Sol. By SN2 Mechanism inverted product obtain and SN1 given both retention and inversion
®
62. HD0062
Ans. (D)
Sol. Due to partial double bond character substitution in is most difficult.

Cl
®
63. HD0063
Ans. (A)
O
Sol. SN2 rate is maximum in as compare to other option due to most stable transition state.
Br
SN2 rate > due to leaving group.
®
Br Cl
>
SN2 rate due to steric factor
Cl Cl
64. HD0064
Ans. (B)
Sol. NaI in DMSO follow SN2 mechanism. SN2 rate of chloro benzyl is fast as compare to other option.
®
65. HD0065
Ans. (A)
CH2– Br CH2–NH2
Sol. + NH3 + HBr
®
Br Br
66. HD0066
Ans. (C)
Sol. CH3 – O – CH2 – Br can form better cation (SN1) as well as better transition state for (SN2)
®
67. HD0067
Ans. (D)
Sol. Chlorobenzene have partial double bond character in carbon chlorine bond. So AgNO3 can not react
with Cl to give white ppt.
®
68. HD0068
Ans. (B)
Sol. Stability of leaving group is more stable if more delocalisation of negative charge of leaving group.
®
69. H D0069
A ns. (B)
Sol. moist Ag2O means Ag(OH)

Ag2O + H2O ® Ag(OH)
®
OH
Br OH
70. HD0070
Ans. (C)
Sol. 2CH3 — CH2 — Br + Ag2O ® C2H5 — O — C2H5 + 2AgBr
Dry
®
71. HD0071
Ans. (B)
CH3 CH3
SOCl2, Pyridine
H OH SN2 Mechanism
Cl H
Sol.
D D
(Inverted product)
®
72. HD0072
Ans. (C)
Sol. PBr3 is suitable for SN2 reaction. In given question inversion (SN2) take place.
®
73. H D0073
A ns. (C)
Sol. CH3 — CH — CH2 — CH2 — CH — CH3

SH(1eq.)
OTs OTS
–OTs SN2
®
S SH
Å
KOH
CH3 — CH — CH2 — CH2 — CH — CH3 CH3 — CH — CH2 — CH2 — CH — CH3
OTs – OTs OTs
CH3 S CH3
74. HD0074
Ans. (A)
CH3 CH3 CH3 CH3
TsCl KSH
H OH H OTs HS H + H SH
Sol. Et Et Et Et
(S) (R) (S)
®
0.95 mole 0.05 mole
out of 0.95 mole 0.05 from SN1
mechanism \ 0.90 mole from
0.90
SN2. So, percentage ´ 100 = 90%
1
75. HD0075
Ans. (B)
Sol. R – OH + SOCl2 ® R – Cl + HCl + SO2
Gas Gas
®
76. HD0076
Ans. (A)
CH3 CH3
SOCl , Et O
H OH (SN mechanism)
2 2
H Cl
i
Sol.
D D
(Retention due to SNi)
®
77. HD0077
Ans. (A)
Sol. Rate if dehydrohalogenation
(A) < due to stable Alkene form from
Cl
Cl Cl
(B) form more stable alkene than
Cl
®
Cl
(C) I– better leaving than Br– of \ form alkene fast

I Br I
(D) Due to weak C – H bond than C – D, CH 3 – CH2 – Cl form alkene faster than CD3 – CD2 – Cl.
78. HD0078
Ans. (D)
Br
O — CH — CH2 KOH O — CH = CH2
Sol. 200°C
–HBr
H
®
79. HD0079
Ans. (C)
Sol. CH3 H
CH3 H
H D
H Br
CH3 D
CH3 Br
E2
®
(Anti C2H5O–/C2H5OH
elimination)
H D
CH3 CH3
80. HD0080
Ans. (B)
Sol. (A) gives hoffmann's product due to poor leaving group
(B) gives Saytzeff due to normal E2 reaction
(C) gives Hoffmann product due to bulkier size base
(D) gives Hoffmann product due to Hoffmann elimination reaction
®
81. HD0081
Ans. (C)
Sol. Rate of Wurtz reaction for R — X is-
R – F < R – Cl < R – Br < R–I
2p – 2p 2p – 3p 2p – 4p 2p – 5p
less overlapping
®
CH2 – F < CH2– Cl < CH2– Br < CH2– I
I II III IV
82. H D0082
A ns. (C)
Br
Sol. NBS Na/Ether

CCl4
Free
Radical
®
ß
83. H D0083
A ns. (C)
Sol. rate of free radical substitution µ stability of free radical
·
(I) CH2 – CH = CH2 Resonance
·
(II) CH3 – CH – CH = CH2 Reso + HC/+ I
·
(III) CH3 – C – CH = CH2 Reso + more + HC/I
CH3
®
So order will be III > II > I
84. HD0084
Ans. (B)
Br
Br2/hv
CH3 – CH – CH2 – CH3 CH3 – C – CH2 – CH3
light
Sol. CH3 CH3
2-bromo-2methyl butane
Bromination reaction is more selective than chlorination and Fluorination
®
85. HD0085
Ans. (D)
Sol. It is hunsdiecker free radical bromination reaction.
O
CH3 – CH2 – C – OAg
Br – Br
O
·· ·
CH3 – CH2 – C – O – Br Br·
CH3–CH2–Br
®
O A
O ·
· · CH3–C–O O
CH3 – CH2 – C – O –CO2 CH3–CH2
H3C–CH2–C–O–CH2–CH3
·
B
CH3–CH2
CH3–CH2–CH2–CH3
C
"D" formation is not possible
86. HD0086
Ans. (C)
Cl
Cl2/hv
Sol. (A) Light
or Only one mono chlorination is possible
Same Cl
Cl
®
Cl2 /H2O
(B)
Cl
Same
Cl
Cl
(C) +
Two diff product
(D) Cl only one mono chlorination

87. HD0087
Ans. (B)
Sol. The structure of free radical species is trigonal planar
®
88. HD0088
Ans. (A)
Sol. neopentane forms only one monochloroalkane product.
CH3 ¬ CH3
¯ Cl2/hv
® CH3 — C — CH3 ® CH3 — C — CH2— Cl
CH3 CH3

®
89. HD0089
Ans. (C)
O OH OH
(I) Mg – Hg
(II) H2O
O OH OH
®
–H2O conc H2SO4/D
Å
ring
contraction
Å
Sol.
OH OH
+
–H
O
Å
OH
90. HD0090
Ans. (C)
Br
2Na
Sol. Dry Ether
Bicyclo
Cl –NaBr
®
–NaCl
91. HD0091
Ans. (A)
Sol. According to selectivity order of chlorination rate will be
CH3
CH3 — C — CH3 CH3 — CH3 CD3 — CD3
CH3 C – D bond
®
stronger than
C – H bond
92. H D0092
A ns. (C)
CH3
CH3 — CH — COOK K.E.S.
CH3 — CH CH
or
CH3 — CH — COOK CH3 — CH CH
Cis CH3 Trans
2CO2
(Major)
®
Sol.
CH3 — CH
trans alkene more
CH3 — CH stable than cis
93. H D0093
A ns. (B)
Sol. Due to formation of OH–, pH of the electrolyte increases progressively as the reaction process
®
94. HD0094
Ans. (B)
Sol. Due to selectivity/reactivity order of chlorine, isobutyl chloride in major amount
Cl2/hv
Light
Cl
®
95. HD0095
Ans. (B)
Cl
Cl2/hv Cl2/hv
Sol.
Cl
Cl
®
Cl2/hv
Cl
X+Y=8
Cl
Cl2/hv Cl
Y
Cl
X
Cl 4 product
4 product formed
excluding stereoisomers
96. HD0096
Ans. (B)
Sol. NBS, CCl4

[P]
peroxide D
in which allylic substitution take place
®
Br
(I) * 2 products
Br
(1) products
Br
*
(II) 2 products
* Br
2 products
Br
(III) *
Br 2-products
S a me
Total = 9 products formed

97. HD0097
Ans. (D)
O
Sol.
Mg – Hg HÅ Å
H2O D
OH OH OH
ring
®
expansion
O OH
(1) Spiro (2) ketone

(3) can show tautomerism (4) D.O.u. = 3
98. HD0098
Ans. (B)
Sol. CH2 — OH CH3

HI
CH — OH excess CH — I
CH2 — OH CH3
®
CH2 — I
CH — I
CH2 — I
HI
unstable due
to big size of I
– I2
CH2 CH3 CH3

HI
CH CH — I –I2 CH
CH2 — I CH2 — I CH2

unstable
99. HD0099
Ans. (B)
Br Å
C º C – CH3
Sol. CH3–CºCNa
D
80% 20%
in which CH3– C º C act as base and Nu both, so SN & E both reaction possible both in case of
2 2
high temperature Elimination product will be major
®
100. HD0100
Ans. (D)
HCl
Sol. R — OOR
Cl
in which addition will be proceeds according to Markonikov rule, BCOz peroxids cannot affect bond
length of HCl

Exercise 1 1686225084

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Exercise 1 1686225084

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JEE (MAIN + ADVANCED) : ENTHUSIAST COURSE

SUBJECT : ORGANIC CHEMISTRY

CH2 ® Octet incomplete

Sol. the above carbocation cannot be formed as it violates BREDT’S RULE

Å So we can see total

Sol. (A) Cl Å DH1

Br Bromo cyclo Propane

ring (1, 2 shift) Å (1, 2 shift) Å

So we can say 3 Þ 1, 2-shifts

No elimination as heat is not given

(I) OH Not possible

Rate Þ IV > III > II > I

Sol. (P) Reso (Q) Reso + 2 a H

(R) > (Q) > (P) > (S)

> > >

P & R are same

Product is Active but product mixture is inactive due to Racemisation

most stable carbocation

So, most reactive is

(I) least stable, No a – H (II) ® most stable, 3a – H

[P] have three optical isomer.

Sol. H3C — C = C — CH2 — OH

H3C — C — C = CH2 H3C — C — C = CH2

Sol. (A) O is most reactive towards SN1

(pp – pp) or backbonding.

Non-aromatic Antiaromatic Aromatic

Order of reactivity towards SN1 µ stability of C+

Sol. Due to partial double bond character substitution in is most difficult.

with Cl to give white ppt.

Sol. moist Ag2O means Ag(OH)

Sol. CH3 — CH — CH2 — CH2 — CH — CH3

OTs – OTs OTs

(C) I– better leaving than Br– of \ form alkene fast

Sol. NBS Na/Ether

Two diff product

(D) Cl only one mono chlorination

CH3 — C — CH3 CH3 — CH3 CD3 — CD3

Sol. NBS, CCl4

in which allylic substitution take place

Total = 9 products formed

(1) Spiro (2) ketone

Sol. CH2 — OH CH3

CH2 CH3 CH3

CH2 — I CH2 — I CH2

high temperature Elimination product will be major

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