JEE Main Organic Compound Containing Halogens Important Questions
JEE Main Organic Compound Containing Halogens Important Questions
JEE Main Organic Compound Containing Halogens Important Questions
Sol. (d)
CH3 CH3 CH3
PCl5 /
H3C C CH2OH H3C C CH2 H C C CH2 CH3
HCl, 3
or,
SOCl2 / Pyridine
CH3 CH3
CH3
Cl
H3C C CH2 CH3
Cl
Cl2 / h
H3C C CH3
H3C C CH2 Cl
CH3 CH3
1
2. Identify (A) in the following reaction
CH3ONa
CH3 + CH3OH (A)
O
CH3
(a) CH3O CH3 (b)
O O OCH3
CH3
(c) CH3O CH3 (d)
HO OH OCH3
Sol. (c)
CH3OH
CH3O CH3 CH3O CH3 CH3O CH3
O O CH3O HO
H+
2. ? Identify the product
OH
(a) (b)
O CH3
OH .. +
OH O O
H
2
O
3. CH 2 CH CH 2 Cl aq
. KOH
A. Which of the following is the
correct structure of the compound ‘A’?
O O
(a) CH 2 CH CH 2 OH (b) HO CH 2 CH CH 2
CH 2 CH CH 2 OH
O O
(c) CH 2 C CH 2 (d) CH2CCH3
OH
Sol. (b)
O
CH 2 CH CH 2 Cl
OH
Me COOH
Z then X, Y, Z are.
Br Br
4
H
|
(d) C 6 H 5 C Cl, SN1, only inversion
|
CH3
Sol. (a)
5
each tube was made acidic with dilute HNO3 and then some
AgNO3 solution was added. Substance B give a yellow
precipitate. Which one of the following statements is true
for this experiment?
(a) A was C6H5I
(b) A was C6H5CH2I
(c) B was C6H5I
(d) Addition of HNO3 was unnecessary
Sol. (a)
6
ortho and/or para positions. The most electron
withdrawing group amongst all is NO2.
11. Identify the set of reagents/ reaction conditions ‘X’ and ‘Y’
in the following set of transformations.
(X) (Y)
CH3CH2CH2Br Product CH3CHCH3
Br
7
12. An unknown alkyl halide (A) reacts with alcoholic KOH to
produce a hydrocarbon (C4H8). Ozonolysis of the
hydrocarbon affords one mole of propionaldehyde and one
mole of formaldehyde. Suggest which organic structure
among the following is the correct structure of the above
alkyl halide (A)?
(a) CH3(CH2)3Br (b) CH3CH(Br)CH(Br)CH3
(c) CH3CH2CH(Br)CH3 (d) Br(CH2)4Br
Sol. (a)
C4H8 is CH3CH2CH = CH2 as it gives propionaldehyde&
formaldehyde on ozonolysis. So, CH3CH2CH = CH2 is
produced by dehydro halogenation of
CH3CH2CH2CH2Br(A)
Sol. (b)
Aryl halides containing electron releasing groups like
OCH3 form benzyne as intermediate when treated with
KNH2 in liquid NH3.
8
14. H H + KI Acetone
P
CH3 Cl
‘P’ is:
(a) CH3 I (b) H H
H H CH3 I
CH3 H H I
Sol. (c)
SN2 reaction proceeds with complete inversion of
configuration.
(c) C H CCl
6 5 3 (d) C H CH Cl 6 5 2
Sol. (c)
(C6H5)3CCl is hydrolysed most rapidly by SN1 because
(C6H5)3C+ is most stable.
Me Me Me
OH– OH–
16. OH H II
H Cl I H OH ( Racemic mixture)
Et Et Et
B A
Steps I and II are:
(a) both SN1 (b) both SN2
(c) I SN1, II SN2 (d) I SN2, II SN1
9
Sol. (c)
SN1 reaction is accompanied by racemisation while SN2
reaction is accompanied by inversion of configuration.
Sol. (c)
CH3 CH3
CH3 CH3
CH2 C CH CH3
CH3 C CH CH3 (major) CH3 CH3
H2/Ni
CH3 CH3 CH3CHCHCH3
Cl
2, 3 Dimethyl Butane
CH3 C CH CH3
(minor)
10
18. In the following reaction,
Cl
H Ph NaI
EtO H acetone
Ph
the structure of product is
I Cl
(a) H Ph (b) H Ph
EtO H I H
Ph Ph
I Cl
(c) Ph H (d) H Ph
EtO H H I
Ph Ph
Sol. (a)
Due to neighbouring group participation of OEt group.
NO2 O2 N
Sol. (c)
Aryl halides containing maximum number of electron
withdrawing groups at the ortho and para positions undergo
hydrolysis most readily.
11
20. Which one of the following form benzyne as intermediate
when treated with KNH2 in liquid NH3:
(a) Cl CHO (b) Cl OCH3
Sol. (b)
Aryl halides containing electron releasing groups like
OCH3 form benzyne as intermediate when treated with
KNH2 in liquid NH3.
CH3 Cl
21. H OH
SOCl2
H D
D CH3
Which of the following statements about the above reaction
is true?
(a) It is unimolecularnucleophilic substitution
(b) It is bimolecular nucleophilic substitution
(c) It is internal nucleophilic substitution
(d) It is unimolecular electrophilic substitution
Sol. (c)
COCH3
COCH3
(a) (b)
12
CN COOH
(c) (d)
Sol. (b)
CH3
+
Br MgBr C=NMgBr CH3C=O
Mg/ether CH3CN
H3O+
(A)
OH OCH3
13
24. The correct order of boiling point is
(a) CH I CH Br CH Cl CH F
3 3 (b) CH Br CH I CH Cl CH F
3 3 3 3 3 3
(c) CH F CH Cl CH Br CH I
3 3 (d) CH Cl CH F CH I CH Br
3 3 3 3 3 3
Sol. (a)
Larger the size of the halogen atom, higher is the B.P.
( CH 3 )3 C O K Cold alk .
26. (CH3)3CBr (A)
NBS
(B) (C).
KMnO4
14
27. For the reaction, R – X + OH– R – OH + X–, the rate
of reaction is given as, rate
= 4.7 10–5 [R – X] [OH–] + 0.24 10–5 [RX]. What
percentage of R – X react by SN2 mechanism when [OH–] =
0.001 molar?
Sol. 1.9
15