Exercise 1 1676446171

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

Topic : HALOGEN DERIVATIVE Exercise : O-2
1. HD0101
Ans. (A,B,C,D)
Sol. SN2 is bimolecular nucleophilic substitution reaction It's rate depends on concentration of nucleophile as well as
concentration of substrate also. It also depends on leaving group nature and solvent nature.
®
2. HD0102
Ans. (A,B,C)
Sol. SN2 reaction is negligible in vinylic and arylic halides and also difficult on bridgehead C – X bond.
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3. HD0103
Ans. (A,B)
Sol.
®
4. HD0104
Ans. (B,D)
Sol. (B) less crowded C – Cl bond in I than II
(D) Less crowded C – Cl bond in I than II
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5. HD0105
Ans. (B,D)
CH3 CH3
CN
H — C — OTs DMF N º C — C — H + TsO
2
Sol. SN
C2H5 C2H5
(S) (R)
®
6. HD0106
Ans. (A,C)
Sol. (A) I is less crowded than II
(B) I is less crowded than II
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7. H D0107
A ns. (A ,D)
Sol. (B) Alkyl Iodides on exposure to sunlight gradually darken due to poor strength of C – I bond
(C) Photo iodination is irreversible in presence of oxidising agents like HNO3/HIO3
These two are correct statements
(A) Tertiary alkyl halides readily undergoes SN1
(D) Alkyl iodides readily undergoes SN reactions among alkyl halides.
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8. HD0108
Ans. (A,C)
Sol. Arylic and vinylic halides are unreactive in SN1 and SN2 reaction.
®
9. HD0109
Ans. (A,B,D)
Cl Cl
Cl2
CH2 = CH — CH2 — Ph CH2 = CH — CH — Ph + CH2 — CH = CH — Ph
500°C
d/l C/T
Sol.
CH2 = CH — CH — Ph CH2 — CH = CH — Ph
Total four products.
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10. HD0110
Ans. (A,C)
Me Me
Na CH3Br
Sol. (A) H OH H O — CH3
D D
Retention
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(B)
Me Me
PCl3 CH3ONa
(C) H OH H O – CH3
SN2 SN2
D D
two inversions will leads to retention
(D)
11. HD0111
Ans. (A,B,D)
Cl
PCl5
Sol. (A) CH3 — CH = O CH3 — CH
Cl
Cl
®
PCl5
(B) CH3 — CO — CH3 CH3 — C — CH3
Cl
Cl
Cl2
(C) CH2 = CH2 CH2— CH2
Cl
Cl
(D) H – Cl
CH2 = CH — Cl CH3— CH
Cl
12. HD0112
Ans. (A,C,D)
Sol. (A) Major product is CH2 = CH – CH2 – CH3 E2 with characters of E1CB.
(B) Major product is CH3– CH = CH – CH3 E2
(C) Major products is CH2 = CH – CH2 – CH3 E i
(D) Major products is CH2 = CH – CH2 – CH3 E i
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13. HD0113
Ans. (A,C,D)
D +
Å
Sol. N OH N N
Major
It is pyrolysis of quaternary Ammonium hydroxide follows E2 Mechanism with character of E1CB so
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Hoffmann's Alkene is major product
14. HD0114
Ans. (A,B,C)
Me3C — O — CH3 ¾¾ ® Me3C – I + CH3– OH
HI
Sol. (A) 1
SN
CH3 — O — CH2 — CH3 ¾¾ ® CH3 — I + CH3CH2 – OH

HI
(B) 2
SN
Ph — O — CH2 — Ph ¾¾® Ph — OH + Ph — CH2 — I

HI
(C) 1
SN
(D) Ph — O — CH3 ¾¾® Ph — OH + CH3 — I

HI
®
2
SN
15. HD0115
Ans. (A,C,D)
®
Sol.
Total brominated products 9.

out of which four enantiomeric pair
Total 5 fractions are obtained on fractional distillation of product mixture.
16. HD0116
Ans. (B,D)
Sol.
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17. HD0117
Ans. (B,D)
Sol. Na
Cl Dryether
Na
®
Cl Dryether
Cl Na + +
+ Dryether
Cl
Cl Na + +
Cl Dryether
18. HD0118
Ans. (AB)
Sol. Conjugated diences give KCP & TCP product
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19. HD0119
Ans. (ABC)
Sol. (A) due to easier removal of Br– in presence of Ag2O
(B) Aq. Ag2O ® H2O + Ag2O ® 2AgOH
(C) Oxygen is a free radical consumer.
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20. HD0120
Ans. (C,D)
Å
Sol. (A) In acidic medium R – OH became R—OH2
(B)
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(C) Elimination is prefer at high temperature
(D) Triphenyl chloromethane easily hydrolysed by SN1
21. HD0121
Ans. (B,C)
Sol. It is common naming system
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22. HD0122
Ans. (B,C,D)
Sol. (A) due to amine flipping
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23. HD0123
Ans. (A,B,D)
CH3 CH3 CH3
Sol. Br2, CCl4 Br

Br
+
Br Br
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Diasteromers
24. HD0124
Ans. (A,B)
®
Sol.
®
25. HD0125
Ans. (A,C)
OH H
+ Å
(leq.)
Sol. OH OH O *
3º carbocation 2 Products
26. HD0126
®
Ans. (A,B,D)
Sol.
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27. HD0127
Ans. (A,B,C,D)
Sol. (A) Cyclopropane can react with Br2/H2O at room temperature
(B) Br· is more stable than Cl· so bromination is more selective
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·
O
(C) can not dimerise due to crowding
· ·
CH2 CH2
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(D) is more stable than
NO2
28. HD0128
Ans. (A,B,C,D)
Sol. Good leaving support SN1, SN2, E1, E2 mech
29. HD0129
Ans. (B)
OH
®
Sol. (iv) Not hydrocarbon
OM DM
Br
Br2
(v) CCl4 Not hydrocarbon
Br
30. HD0130
Ans. (A,B,C)
®
Na
Dry Et2O
Sol.
Cl
Cl
Wurtz reaction (free radical mech)
31. HD0131
Ans. (A,C)
Sol. Ph - CH = CH 2 + ¾¾¾
BrCCl3
®
Peroxide
·
RO· + Br — CCl3 ® RoBr + C Cl3

Exercise 1 1676446171

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Exercise 1 1676446171

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JEE (MAIN + ADVANCED) : ENTHUSIAST COURSE

SUBJECT : ORGANIC CHEMISTRY

CH3 — O — CH2 — CH3 ¾¾ ® CH3 — I + CH3CH2 – OH

Ph — O — CH2 — Ph ¾¾® Ph — OH + Ph — CH2 — I

(D) Ph — O — CH3 ¾¾® Ph — OH + CH3 — I

Total brominated products 9.

CH3 CH3 CH3

Sol. Br2, CCl4 Br

(C) can not dimerise due to crowding

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