Halogen Derivatives PDF

FINAL TOUCH
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
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 F.T.R. BY N.J. SIR
Single Choice Exercise
CH3
Br H
1. H CH3 + NaI  product ; SN2 product of the reaction is :

Acetone
CH2 CH3
CH3 CH3
I H H I
(A) (B)
H CH3 H CH3
CH2 CH3 CH2 CH3
CH3 CH3
I CH3 I H
(C) (D)
H CH3 CH3 H
CH2 CH3 CH2 CH3
Ans (B)
2. Rate of S N 2 will be negligible in :
Br Br Br Br
(A) (B) (C) (D)
Ans. (C)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
3. What is the major product obtained in the following reaction ?
CH2 Br
NH3
Product
EtOH
Br
CH2 NH2 CH2 Br CH2 NH2 CH2 NH2

(A) (B) (C) (D)
Br NH2 NH2
Ans (A)
CH3
–
4. Cl CH2 C CH2 CH2 Cl +I  
DMF
 product ; Major product of this reaction is :
CH3
CH3 CH3
(A) I CH2 C CH2 CH2 Cl (B) Cl CH2 C CH2 CH2 I
CH3 CH3
CH3 CH3
(C) H2C C CH2 CH2 Cl (D) Cl CH2 C CH2 CH2 CH2
CH3
Ans (B)
Acetone
5. H F + NaI (1 Mole)  A ; Major product of this reaction is :
(Major)
Br H
(A) H F (B) I F
I H H H
I H
(C) H (D) H
Br H Br I
Ans (B)
6. Identify products of the given reactions :
OTs
CH3CO2 Na
Product
Reaction-1 CH3CO2H
NMe2
OTs
CH3CO2 Na
Product
Reaction-2 CH3CO2H
NMe2
O CH3
O CH3
; +Enantiomer
O
(A) O
NMe2
NMe2
O CH3
(B) O + Enantiomer ;
NMe2
O CH3
(C) O single product is obtained in both the reactions

NMe2
O CH3
(D) O single prooduct obtained in both the reactions

NMe2
Ans. (A)
(C4H8ClONa)
7. 4 - chloro -1 butanol +NaOH (A) (B)
Et2O 
Product (B) of the above reaction is :
CH3
CH2 CH3
(A) (B) (C) O (D)
O O O
Ans (B)
Me H
KSH
8. Et D   Product ; Identify the product.
SH H
Me H Me H
(A) (B)
Et D Et D
H SH
H SH
HS Me H Me
(C) (D)
Et D Et D
H H
Ans. (D)
CH3
SO2Cl2 NBS KSH

9. (A) (B) (C) , Product (B) is
h
SH SH Br Br
(A) Br (B) Cl (C) SH (D)
Ans. (B)
10. Product (s) formed during this reaction is / are :
*
CH OTs
CH2 2
AcONa
Product ? [C* = isotopic carbon]
AcOH
* OAc * OAc
CH2 CH2 CH2 CH2
(A) (B)
* OTs
CH2 CH2
(C) (D) Both (A) and (B)
OAc
Ans. (D)

NMe3
HO– A
11. (Major)

Major product A is :
(A) (B) (C) (D)
Ans (B)
O
Br
alc.KOH
12. Reaction (1)   (A) (major)
alc.KOH
Reaction (2)   (B)(Major)
Br
alc.KOH
Reaction (3)   (C)(Major)
Br
Product obtained in above reactions (1), (2) & (3) is:

(A) A = B but C is different (B) A = C but B is different
(C) B=C, but A is different (D) A = B =C all product are identical
Ans. (D)
Cl
Cl Cl
3mole alc.KOH
13. Rection (1)   (A)
Cl Cl
Cl
Cl
Cl Cl
3mole alc.KOH
Reaction (2)   (B)
Cl Cl
Cl
Cl
Cl Cl
3mole alc.KOH
Reaction (3)   (C)
Cl Cl
Cl
Product obtained in above reactions (1),(2) & (3) is :

(A) A=B, C different (B) A=C,B is different
(C) B=C,A is different (D) A=B = C is same
Ans. (D)
alc.KOH
14. (x)
Br x is number of E2 product obtained
(including stereoisomers)
Find (x).
(A) 3 (B) 4 (C) 5 (D) 6
Ans (C)
CH3
NaOEt
15. ; Major product of the reaction is :
(E2 reaction)
Cl
CH3 CH3 CH3 CH3
(A) (B) (C) (D)
Ans (B)
CH3
NaOEt
16. Cl ; Major product of the reaction is :
CH3 CH3 CH3 CH3
(A) (B) (C) (D)
Ans (A)
17. End product (D) in the given sequence is :
CH3I
CH3NHCH3 BaO (2 molar equivalent) Ag2O/ H2O
Br Br (A) (B) (C) (D)+(CH3)3 N
2 molar equivalent
O CH3
(A) (B) (C) (D)
O OH
Ans (B)
18. The following bimolecular elimination reaction (E2) is carried out with different halogen leaving groups. The per cent
yield of the two products (2- hexene and 1-hexene) for each leaving group is listed below.
X
+ CH3O– E2 +
Leaving group Conj. Acid pKa % yield of 2-hexene % yield of 1-hexene

X=I -10 81% 19%
X=Br -9 72% 28%

X=Cl -7 67% 33%
X=F 3.2 30% 70%
Which of the following statement is (are) true concerning this series of E2 reactions ?
(A) Based on the pKa’s of the conjugate acid., I– is the best leaving group and F– is the poorest leaving group
(B) When I– , Br– Cl– are used as leaving groups, Zaitsev’s rule is followed
(C) F- is the strongest base (and therefore the poorest leaving group) and the transition state for reaction with
fluoride as the leaving group has the least double bond character
(D) a,b,c are true
Ans (D)
Ph
conc.H2SO4
19. Major product of the reaction is :
Ph OH
Ph
(A) (B)
Ph
Ph Ph Ph
(C) (D) None of these
Ph
Ans. (B)
Br
1. One eq. NaCN
(A) ; Product (A) is :
20. 2. LiAlH4
Br
Br Br
(A) (B)
CH2-NH2
CH2NH2 CH2-NH2
(C) (D)
Br Br
Ans. (C)
Br
21. , which is not the correct statement :
(I)
(A) I is more soluble than bromocyclopropane
(B) I gives pale yellow ppt. on addition with AgNO3
(C) I is having lower dipole moment than bromocyclopropane
Br
(D) I is more ionic than
(I)
Ans. (C)
22. How many 1, 2- Shifts are involved during the course of following reaction.
OH
conc. H2SO4
(A) 1 (B) 2 (C) 3 (D) 4

Ans. (C)
CH3
CH3 H+
23. (X) (Major)
OH
Product (X) is :
CH3 CH3 CH3 CH3
(A) (B) (C) CH3 (D)
CH3 CH3 CH3
Ans. (A)
OH +
H
24.
5ºC
P . The product P is :
OH
(A) (B) (C) (D)
Ans. (D)
OH
H2SO4
25. X ; X is :
OH
OH OH O
(A) (B) (C) (D)
OH
Ans. (D)
a b
26. c The double bond which is most reactive towards electrophile :
O
(A) a (B) b (C) c (D) None
Ans. (B)
27. How many products are obtained in the given reaction :
Et Ph CH3 Ph
H2SO4
HO OH + HO OH
Et Ph CH3 Ph
(A) 1 (B) 2 (C) 3 (D) 4
Ans. (B)
28. What is the order of reactivity with HBr :
(a) (b) (c)

CH3O CH3O
(A) a > b > c (B) b > a > c (C) c > b > a (D) b > c > a
Ans. (B)
OH
29. 'P' (Major Product)
O
O O
(A) (B) O (C) (D)
O O OH
Ans. (B)
30. Arrange the following compounds in decreasing order of electrophilic addition :

O–CH 3 Cl
'P' 'Q' 'R'

(A) P > Q > R (B) P > R > Q (C) R > P > Q (D) R > Q > P
Ans. (B)
C = CH2
HBr
31. H D Product (without rearrangement of carbocation )
CCl4
CH3
What is stereochemistry of product :
(A) Racemic mixture (B) Optically inactive
(C) Mixture of diastereomers (D) Meso product
Ans. (C)
HBr
P
32. (i)CH3I If P & Q are the major products then P & Q are respectively ?
N (ii)HBr
Q
Br Br
; ; Br
(A) N N I
–
(B) N Br N I
–
Br Br
; ; Br
(C) N Br N I
–
(D) N N I
–
Ans. (C)
33. In the given reaction :
H
N Br2
[X],[X] is
H H
Br N
N N
Br N
(A) (B) (C) Br (D)
Br Br Br
Ans. (D)
34. Select incorrect statements about product (P) of the reaction :

H Me
Br 2/CCl4
P
Me H
(A) P is optically inactive due to internal compensation
(B) P is optically inactive due to the presence of plane of symmetry in the molecule
(C) The structure of P can have three optical isomers possible
(D) P can have four possible optical isomers
Ans. (D)
CH3
HOH
35. H I Products. (If 96% racemisation takes place)
Et
Find out the correct statement about the reaction.
(A) Among the products 48% S and 48% R configuration containing molecules are present
(B) Among the products 50% S and 50% R configuration containing molecules are present
(C) Among the products 48% S and 52% R configuration containing molecules are present
(D) Among the products 52% S and 48% R configuration containing molecules are present
Ans. (C)
36. When ethyl bromide is treated with moist Ag2O, the main product is :
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All these
Ans. (B)
37. When ethyl bromide is treated with dry Ag2O, the product is :
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these
Ans. (C)
38. Which reaction conditions (reagents) is suitable for the following reaction :
?
H – C – OH Br – C – H
D D
(A) Br2/CCl4 (B) SOBr2 (C) PBr3 (D) HBr / conc H2SO4
Ans. (C)
39. In the given reaction
(i) SH(1eq.)
(ii) KOH
CH3 – CH – CH2 – CH2 – CH – CH3 (X), X will be.
OTs OTs
OTs S S S
(A) CH3 – CH – CH2 – CH2 – CH – CH3 (B) CH3 – CH – CH2 – CH2 – CH – CH3
CH3 CH 3
(C) CH3 S CH3 (D)
S
Ans. (C)
CH3
TsCl KSH
40. H OH (A) Products.
Et
(1 mole)
(Assuming all the substrate convert into substitution products containing 0.05 mole of S-configuration) Calculate
the percentage of SN2 mechansim.
(A) 90 % (B) 80 % (C) 70 % (D) 95 %
Ans. (A)
NBS Na/ ether

41. CCl4. Peroxide (X) ; X is
(A) (B)
(C) (D) None of these
Ans. (C)
42. Consider the following reactions
Cl2/hv Total number of monochlorinated product = X (Excluding stereoisomers)
Cl2/hv
Total number of monochlorinated product = Y (Excluding stereoisomers)
Identify value of X + Y.
(A) 8 (B) 9 (C) 11 (D) 10
Ans. (A)
Br
43. In the given reaction :
and
(A)
20% 80%
+
(B)
20% 80%
(C) (D)
100% 100%
Ans. (B)
44. Number of following reactions which produces hydrocarbon as major product ?
O
Na Electrolysis
(i) CH 3 – CH 2 – Cl (ii) CH3 – C – OK
Et2O
Br2
CH2 – CH2 dust
(i) Hg(OAc)2/H2O
(iii) (iv) (ii) NaBH4
Cl Cl
Br2 (i) B2H6-THF
(v) CCl4
(vi) CH3 – CH 2 – CH = CH2 (ii) CH COOH/H O
3 2
(A) 2 (B) 4 (C) 5 (D) 6

Ans. (B)
H3C CH3
(B) C=C + HI B
H3C H
45. Find out the number of 1–2–shifts during the conversion of
–
B /
–BH

(A) 2 (B) 3 (C) 4 (D) 5

Ans. (B)
46. Select reactions from the following showing incorrect product formations -
OH
Cl
Red P
(A) CH3 COOH CH2 COOH (B) PCl3
Cl2
Me Me
Me Me
PCl5 Cl
PCl5
(C) (D) Me CHO Me CH
O
Cl
H H
Ans. (C)
47. Chloral + Cl 

Conc.H 2SO4
 product. The product is
(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

Ans. (B)
48. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is :
H H
1 2 + 4 5
H 3C C C C CH3
3
HO H CH3
(A) CH3 at C – 4 (B) H at C – 4 (C) CH3 at C – 2 (D) H at C – 2

Ans. (D)
49. AgCN H2 .Ni

Br   A  B
The final product (B) is :
H
NH2
(A) (B) N (C) N (D) NH2
H
Ans. (B)
50. A solution of (+) -1-chloro-1-phenylethane in toluene racemises slowly in the presence of small amount of SbCl5,
due to the formation of
(A) Carbanion (B) Carbene (C) Free-radical (D) Carbocation
Ans. (D)
51. Identify the set of reagents/reaction conditions 'X' and 'Y' in the following set of transformations -
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)
52. Identify major product of reaction ?
Br2 Alcoh. NBS

h

KOH/ 
  product
Br
(A) (B) Br (C) Br (D)
Ans. (B)
53. The correct nucleophilicity order is :
ONa ONa ONa

ONa
(1) CH3 OCH3 Cl

(2) (3) (4)
(A) 1> 2 > 3 > 4 (B) 3 > 2 > 1 > 4 (C) 3 > 2 > 4 > 1 (D) 2 > 1 > 3 > 4
Ans. (B)
54. Which one is correct for the products of the given reaction
Me
Me
H aqueous acetone
CN 
H H
H
Cl
OCH3
Me Me Me
Me Me Me
H H H
CN CN HO CN
H H OH H H H
H H H
OH H H
OCH3 OCH3 OCH3

(X) (Y) (Z)
(A) only X and Z are formed (B) Z > Y (amount)

(C) X > Y (amount) (D) Y > X (amount)
Ans. (D)
55. Which one will undergo hydrolysis (solvolysis) more rapidly amongst the given pairs of compounds
(X) (Y)
Br
(I)
Br
Cl
Cl
(II)
HO
(III)
I Cl
(IV) Br
Br
I II III IV
(A) x> y y>x x> y x> y
(B) y>x y>x x> y x> y
(C) x> y x> y y >x y>x
(D) y>x y>x x> y y>x
Ans. (D)
56. The correct order of SN2/E2 ratio for the % yield of product of the following halide is
Ph
(P) CH3 CH2 C CH3 (Q) CH 3 CH CH CH 3
I Ph I
(R) CH3 – CH2 – I (S) CH 3 CH 2 CH CH 3

I
(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S
Ans. (A)
57. The structure of the starting material X is :
PBr3 Mg/Ether
Y Z H3O 
X Na2Cr2O7,H2SO4 S   3, 4- Dimethyl - 3 - hexanol
W
OH
(A) OH (B) (C) OH (D)
OH
Ans. (B)
NaSMe
58. Br 
DMSO
 Major product
Cl
D D
(A) Br (B) Br
SMe SMe
D D
(C) MeS (D) MeS
SMe SMe
Ans. (A)
Multiple Choice Exercise

14
HI
Br – CH – CH = CH2
1.
CH3
Products which can be obtained during the reaction in good yield :
14 14
(A) Br – CH – CH –I (B) I – CH – CH – Br
CH3 CH3 CH3 CH3
14 14
(C) Br – CH – CH2 – CH2 – I (D) I – CH – CH2 – CH2 – Br
CH3 CH3
Ans. (A,B)
2. Consider the given reaction

CH3
NaCN
H C OTs CH3CH2CH – CN
(DMF)
C2H5
CH3
which of following statements is/are correct for the above reaction.
(A) Product formation takes place due to the breaking of O – Ts
(B) The reaction is SN2
(C) The reaction is SN1
(D) Configuration of product is (R)
Ans. (B,D)
3. Correct statement (s) for the product (s) of following reaction.
CH2 = CH CH2 – Ph 
Cl2 500ºC

(A) Four different products are formed
(B) Two optically active products are formed
(C) The optically active compound formed here can also be made by the reaction of HCl
(D) The reaction path is free radical substitution
Ans. (A,D)
4. In which product formation takes place according to Hoffmann’s rule
t-BuOK CH3CH2OK
(A) CH3CH2 – CH – CH3 (B) CH3 – CH2 – CH – CH3
Br Br
CH3
OH
(C) CH3CH2 – CH – N OH (D) CH3CH2CH – CH3
CH3
CH3
CH3 S(CH3)2
Ans. (A, C, D)
5. Which of following are correct for given reaction
N OH
H3C
(A) Major product of reaction is N (B) Major product is N
(C) The reaction is thermal elimination reaction (D) The reaction is E2 reaction
Ans. (A, C, D)
6. In which case incorrect products are formed :

HI
(A) Me3C – O – CH3   Me3 C – OH + CH3I
HI
(B) H3C – O – CH2 – CH3   CH3 OH + ICH2CH3
HI
(C) O – CH2 I+ CH2 – OH
OH
HI
(D) Anisole  + CH3I

Ans. (A, B C)
7. In the given reaction : NBS
Find out the correct statement

(A) It gives total 9 allylic brominated products
(B) 6 fractions are obtained on fractional distillation of product mixture
(C) Substrate has 7 allylic hydrogens
(D) NBS is a brominating agent for allylic positions
Ans. (A, C, D)
8. Product obtained in given reaction in good yield are :
HBr
(A) (B)
Br
Br
(C) (D) Br
Br
Ans. (A, B)
H+
OH
9. 1.eq.
OH
Correct statements for given reaction :
(A) Product mixture is resolvable
(B) Product can be separated by fractional distillation of mixture
(C) Two products possible & both are optically active
(D) Products are diastereomer
Ans. (A, C)
10. Which of the following can be formed during this reaction ?
H3O+
OH
OH
(A) (B)
OH OH
(C) (D)
O O
Ans. (A, B, D)
Na
11. Product
in Et2O
Cl
Cl
Correct statement is / are :
(A) odd no. of double bond equivalent in product
(B) product is bicyclic compound
(C) product can show geometrical isomerism
(D) reaction involve carbocation as intermediate
Ans. (A, B, C)
12. Ph – CH = CH2 + BrCCl3 

Peroxide
  Product is :
H H
(A) Ph CH2CCl3 (B) Ph CH2Br
Br CCl3
Br CCl3
(C) Ph CH2CCl3 (D) Ph CH2Br
H H
Ans. (A, B)
CH3 Cl
13. Na/(Dry ether)

CH3  
CH2 Cl
Products obtained in above Wurtz reaction
CH3
(A) (B)
CH3 CH3 CH3
CH3
(C) (D)
CH3 CH3 CH3
Ans. (A, B)
14. Select the correct informations about product in reactions I and II.
H Br
NaI/Acetone
(I)
AgF (Protic solvent)
(II)
H3C H
(I) (II)
H CH3 H CH3 H CH3
(A) +
I H F F H
H
H I I H H F
(B)
H3C H H3C H H3C H
I CH3 F H F CH3
(C) +
H H CH3 H H
H
(D) SN2 SN1
Ans. (A, D)
15. Which of the following can be the product/s of following reaction
Me
H NaOH
Br  
D
Me H Me OH
(A) H (B) Me (C) HO (D) H

D OH H Me
OH D D D
Ans. (A, B, C, D)
16. The correct statement/s about the following is / are
CH3
I*
NaI / Acetone
  'Y'
(A) The product is achiral compound

(B) The product does not have isotopic iodine
(C) It is an allylic biomolecular nucleophilic substitution reaction
(D) Ozonolysis product of ‘Y’ give positive iodoform test
Ans. (A, B, C, D)
17. Which of the given compounds can be the main products of following reaction
Br2 /aq.NaCl  NaI  NaNO3
CH3 – CH = CH2  
(A) CH3 CH CH2 (B) CH3 CH CH2 ONO2
Br Cl Br Cl
(C) CH3 CH CH2 (D) CH3 CH CH2
I Br OH Br
Ans. (C, D)
18. Enthalpy
Reaction co-ordinate
out of the following which one is/are correct
NO2 
E E

(A) 1, + H (B) 2, E (C) 3, H (D) 4,

H
H E
Ans. (A, B, C, D)
NBS HBr
19. CCl4/hv (X) + (Y) enantiomeric pair
Br Br Br
Br
(A) (B) (C) (D)
Br Br Br
Br
Ans. (B, D)
Mis. Exercise
Subjective
1. Encircle whichever of the following :
CH3
(a) undergoes an S N 2 reaction more rapidly : CH2 Br or
Br
CH3 CH3
CH CH2 CH2 C CH2 CH3
(b) Undergoes an E1 reaction more rapidly : Br Br
or
Br
(c) Undergoes an S N reaction more rapidly :

1 or
Br
Cl
Cl
(d) Undergoes an S N 2 reaction more rapidly : or
Cl
Cl
(e) Undergoes an E2 reaction more rapidly : or
2. Select which reaction from the following reaction pairs will occur faster .
PART-1
I OH
H2 O
CH3 CH3
Reaction A DMSO
I OH
H2O
H H
Reaction B DMSO
PART-2
Cl I
NaI
Reaction C CH3 DMSO CH3
CH2Cl NaI CH2l
Reaction D DMSO
PART-3
I Cl
NaCl
Reaction E H DMSO H
I Cl
NaCl
Reaction F H EtOH H
PART-4
I N3
NaN3
Reaction G H DMSO H
Br N3
NaN3
Reaction H H DMSO H
PART-5
CH2 Cl CH2 I
NaI
Reaction I
acetone
Br I
NaI
acetone
Reaction J
CH3 CH3
O
PCl5 x NaNH2 CH3I
3. Reaction- 1 : Ph C CH3 Ph C C CH3
Br y NaNH2
CH3 C C CH3
Reaction - 2 :
Br
Reaction - 3 : Ph CH CH 2 z NaNH2 Et-I

Ph C C Et
Cl Cl
x,y,z are moles used.
Sum of [x + y + z = ]
4. Sum of hydrogen in major product of the reaction.
OH
H+
Reaction -1 (A)

OH
H+
Reaction-2 (B)

OH
Reaction 3 H+
(C)

OH
Reaction-4 H+
(D)

Sum of -hydrogen is A + B + C + D =
5. Select whether the following reagent combination will result in elimination or substitution reactions leading to the
major product.
Reaction Substitution Elimination
CH3

K OC(CH3)3
(a) CH3 C Cl
CH3
H2SO4
(b) CH3 C OH
CH3
Cl
(c) CH3 CH CH2 CH3 alc-KOH
CH3 
Na N3
(d) CH3 C l
Cl
CH3 EtO–
(e) 
CH3
(f) CH3 C Cl
CH3
6. RCl is treated with Li in ether to form R – Li, R – Li reacts with water to form isopentane. R – Cl also reacts with sodium
to form 2, 7 – dimethyloctane. What is the structure of R – Cl .
7. A chloroderivative ‘X’ on reduction gave a hydrocarbon with five carbon atoms in the molecule . When X is
dissolved in ether and treated with sodium, 2, 2, 5, 5-tetramethyl hexane is obtained.
What is compound X.
8. With the help of following data show HBr exhibits the peroxide effect.
H10 / kJmol –1 H 02 / kJmol –1
   
H–H X  CH 2  CH 2  XCH 2 – C H 2 XCH 2 – C H 2  H  X  XCH 2 CH 3  X

HCl – 67 +12.6
HBr – 25.1 – 50.2
HI + 46 – 117.1
9. What are the products of the following reactions ?

(a) Ph CH = CHCH3 + HBr A
H3C CH3
(b) C=C + HI B
H3C H
CH3
Peroxide
(c) +HBr C
CH3
+HCl D
(d)
CH2CH3
10. If required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0g) and form a non resolvable product. On
treatment of (A) with HBr it yielded monobromo alkane (B). The same compound (B) was obtained when (A) was
treated with HBr in presence of peroxide. Write down the structure formula of (A) and (B) and explain the reactions
involved .
11. Complete following reaction
H CHl Br2 Cl2

(A) CH2 (B) CCl4 (C) CS2
CH3
CH3
12. CH  C – CH2 – CH = CH2 , adds up HBr to give CH  C – CH2 – CHBr – CH3 while CH  C – CH = CH2 adds up HBr
to give CH2 = C. Br. CH = CH2.
13. What are the products of the following reactions?

CH3 CH3
(a) CH3 – C – Cl + OCH3 (b) CH3 – C – O+ CH3 –X
CH3 CH3
14. A primary alkyl bromide (A) C4H9Br reacted with alcoholic KOH to give compound (B). Compound (B) reacted with
HBr to give an isomer of (A) . When (A) was reacted with sodium metal it gave compound (D), C8H18, which was
different from the compound produced when n- butyl bromide was reacted with sodium. Draw the structure of (A)
and write equations for all the reactions .
15. In study of chloronation of propane four products (A, B, C, D) of molecular formula C3H6Cl2 were obtained. On
further chloronation of the above products A gave one trichloro product, B gave two whereas C and D gave three
each. When optically active C was chlorinated one of trichloro propanes was optically active and remaining two
were optically inactive. Identify the structures of A, B, C and D, and explain formation of products. Total number of
vicinal dichloride are :
16. The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the following
compound, is
CH3
C
CH3CH2 CH2CH3
H
Comprehension
Paragraph - 1 (17-18)
17. Select whether the following combinations of reactants will react by substitution ( SN1 or S N 2 mechanism), elimi-
nation (E1 or E2 mechanism)
NaI in acetone
Br
A. 25°C
(a) SN1 (b) S N 2 (c) E1 (d) E2
Cl
B. NaOCH3 in methanol
0
50 C
(a) SN1 (b) S N 2 (c) E1 (d) E2
Cl
NaOCH3 in methanol
C. 250C
(a) SN1 (b) S N 2 (c) E1 (d) E2
D. (CH3)3 C OH HBr 48%

0
in H2O
25 C
(a) SN1 (b) S N 2 (c) E1 (d) E2
NaCN in ethanol
E. (CH3)2 CH Br 0
25 C
(a) SN1 (b) S N 2 (c) E1 (d) E2
H H
Br NaCN in ethanol
F. 0
25 C
(a) SN1 (b) S N 2 (c) E1 (d) E2
HBr 48%in H 2O
G. (CH3)2 CHCH 2CH2 OH 0
50 C
(a) SN1 (b) S N 2 (c) E1 (d) E2
X
E2 reaction
18. +
(Hoffmann product) (Saytzeff product)
(A) In the above reaction, maximum Saytzeff product will obtained when :
(a) X = -I (b) X = -Cl (c) X = -Br (d) X = -F
(B) In the above reaction Hoffmann product is major when X is :
(a) -I (b) -Cl (c) -Br (d) -F
Passage (19-20)
A flask contains “mixture” of unknown Alkenes obtained by treatment of 2-chlorobutane with alc. KOH. When the
“mixture” is boiled, the fraction that comes our firstly is A.
19. A on Hydrogenation followed by Treatment with Cl2/h gives how many monochloro products (only structural
isomers)
(A) 1 (B) 2 (C) 3 (D) 4
20. The remaining Alkene mixture is ozonolysed carefully in presence of Zinc and Products atr treated with mixture of
NH2OH. How many oximes obtained.
(A) 2 (B) 3 (C) 4 (D) 5
Passage for (21-23)
Observe the following reactions and given answers
O
OC H CH2CH3
C HCOOH C + C
H3C CHCH3 H3C CH2CH3 H3C OC H
(I)
Ph Cl Ph Ph O
N3
H CH2CH3
C N3 C CH2CH3
Ph (II)
H
Cl
Ph
Br Ag+/H O OH
2
(III)
Br Br
Br
H2O
C C
(IV)
Br O
21. Which of the following structure represents the transition state of slow step of reaction I.
Cl
H H
H H
C C C C
CH3 CH3
(A) H3C Ph (B) H3C Ph
O C H O C H
O O
CH2 CH3
Cl
C Cl H
H
(C) H3C (D) C C
Ph CH3
H3C Ph
22. Which of the reaction (I-IV) involves rearrangement of reaction intermediate.

(A) I only (B) I, III (C) II, III, IV (D) I, II, III
23. Planar reactive intermediates are formed in reactions :
(A) I, III (B) II, III (C) I, II (D) I, III, IV
Comprehension (24-26)
Observe the following experiment
24. If the reactant ‘P’ is ethyl chloride then the product R can be
(A) (B) CH3CH2 – O – CH2CH3
(C) (D)
25. If the liquid Q is H  C  OC2H5 then the product R can be (P can be any other halide)
||
O
(A) (B) (C) (D)
26. If R is then P and Q can be respectively..
(A) , CH3 – – OC2H5 (B) CH3 – Cl,
(C) CH3 – – CH3, (D) , CH3Cl
Match The Column

27. Matrix :
Column (I) Column (II)
Compound Type of reaction
Cl
(A) (p) SN1 reaction can take place
Cl
(B) (q) S N 2 reaction can take place
Cl
(C) (r) SN1 is not possible
Cl
(D) (s) S N 2 is not possible
28. Match the column :

E2 reaction No of possible products.
(elimination bimolecular) (including stereoisomerism)
Br
(A) alc.KOH (p) 0

alc.KOH
(B)  (q) 1
Br
alc.KOH
(C)  (r) 2
Br
alc.KOH
(D) Br (s) 3

29. Match the Column :
HEM = Hoffmann exhaustive methylation followed by elimination.
Reaction Product
(A) HEM HEM (p) H2C CH CH2 CH CH2

N
H
(B) HEM HEM (q) H 2C CH CH2 CH2 CH CH2

N
H
CH3
(C) HEM HEM (r) H2C CH CH2 C CH2

N
H
CH3
(D) HEM HEM (s) H2C CH CH CH CH2

N
H
30. Match the column

Column-I Column-II
Ph
(A) Ph (P)
OH
(B) (Q)
OH
OH
(C) (R)
(D) OH (S)
31. Match the mechanism/s mentioned in List-2 with reactions of List - 1. More than one options of List- 2 can match
with one reaction of List-1.
List -1 List -2
Reactions Mechanism
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

C2H5OH/ C OC2H5
(a) CH3 C C C Cl CH3 C C C CH2 + CH3 C C (P) = SN1
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3
H H CH3ONa/CH3OH/60° + H H3CO
(b) (Q) = E1Cb
CH2 H CH2 H
CH3 I
CH3 H H I
(c) NaI/Acetone (R) = E1
H Cl reflux
H3C H
(d) Ph C NaOH/ (S) = E2

CH2 CH CH3   Ph C CH CH CH3
O OH O
(T) = SN2

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FINAL TOUCH

Single Choice Exercise

1. H CH3 + NaI  product ; SN2 product of the reaction is :

CH2 CH3 CH2 CH3

CH2 CH3 CH2 CH3

2. Rate of S N 2 will be negligible in :

(A) (B) (C) (D)

3. What is the major product obtained in the following reaction ?

CH2 NH2 CH2 Br CH2 NH2 CH2 NH2

6. Identify products of the given reactions :

(C) O single product is obtained in both the reactions

(D) O single prooduct obtained in both the reactions

SO2Cl2 NBS KSH

(A) Br (B) Cl (C) SH (D)

10. Product (s) formed during this reaction is / are :

(C) (D) Both (A) and (B)

(A) (B) (C) (D)

Product obtained in above reactions (1), (2) & (3) is:

Product obtained in above reactions (1),(2) & (3) is :

CH3 CH3 CH3 CH3

(A) (B) (C) (D)

CH3 CH3 CH3 CH3

(A) (B) (C) (D)

17. End product (D) in the given sequence is :

(A) (B) (C) (D)

Leaving group Conj. Acid pKa % yield of 2-hexene % yield of 1-hexene

X=Br -9 72% 28%

(C) (D) None of these

(A) 1 (B) 2 (C) 3 (D) 4

27. How many products are obtained in the given reaction :

(a) (b) (c)

30. Arrange the following compounds in decreasing order of electrophilic addition :

'P' 'Q' 'R'

34. Select incorrect statements about product (P) of the reaction :

39. In the given reaction

NBS Na/ ether

(C) (D) None of these

42. Consider the following reactions

Cl2/hv Total number of monochlorinated product = X (Excluding stereoisomers)

(A) 2 (B) 4 (C) 5 (D) 6

45. Find out the number of 1–2–shifts during the conversion of

(A) 2 (B) 3 (C) 4 (D) 5

47. Chloral + Cl 

(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

(A) CH3 at C – 4 (B) H at C – 4 (C) CH3 at C – 2 (D) H at C – 2

49. AgCN H2 .Ni

ONa ONa ONa

(1) CH3 OCH3 Cl

OCH3 OCH3 OCH3

(A) only X and Z are formed (B) Z > Y (amount)

(R) CH3 – CH2 – I (S) CH 3 CH 2 CH CH 3

57. The structure of the starting material X is :

Multiple Choice Exercise

2. Consider the given reaction

5. Which of following are correct for given reaction

(A) Major product of reaction is N (B) Major product is N

6. In which case incorrect products are formed :

7. In the given reaction : NBS

Find out the correct statement

8. Product obtained in given reaction in good yield are :

10. Which of the following can be formed during this reaction ?

12. Ph – CH = CH2 + BrCCl3 

13. Na/(Dry ether)