QUIZ (CHEMISTRY)

ALKYL HALIDE & ARYL HALIDE

NAME: ………………................ M.MARKS: M.Time: minutes SUB: CHEMISTRY
1. Which one of the following go through benzyne mechanism majorily when treated with KNH2 in
liquid NH3:
(A) Cl CHO (B) Cl OCH3 (C) Cl NO2 (D) Cl COCH3

2. Which of the following statements is wrong about SN2 reaction?

(A) The rate of reaction is independent of the concentration of nucleophile.
(B) Nucleophile attacks the carbon from the side opposite to where the leaving group is attached.
(C) Only in one step the bond formation and bond breaking take place.
(D) The rate of reaction  [substrate] [nucleophile].
3. Which of the following compounds would not give precipitate with AgNO3?
(A) CH 3  CH  CH  Cl (B) CH2  CHCH2 Cl (C) Ph  CH 2  Cl (D) (CH3)3CCl

CH3 CH3CH2OH/heat
(X)
4. (Major) Identify (X) and (Y) formed in the given reaction.
CH3 C Br
CH3 CH2ONa
(Y)
(CH3CH2OH)
CH3 (Major)
CH 3
|
(A) CH 3  C  CH 2 in both cases (B) CH  C  OC H in both cases
| 3 2 5
|
CH3 CH 3
CH3 CH3
|
(C) CH 3  C  CH 2 and CH  C|  OC H (D) CH  C  OC H and CH  C  CH
3 2 5 3 2
| 3
|
2 5
| |
(X) CH 3 CH3 (Y) CH3 (X) CH3 (Y)

Br Br Br Br Br

5. O NH
O
O
(I) (II) (III) (IV) (V)
Ease of SN1 reactions among these compounds upon treatment with aqueous NaOH will be in the
order as:
(A) (I) > (II) > (III) > (IV) > (V) (B) (IV) > (I) > (III) > (II) > (V)
(C) (I) > (IV) > (III) > (II) > (V) (D) (V) > (IV) > (III) > (II) > (I)
6. The correct order of SN2 reactivity among the following is
(A) CH2Cl H2 C CH2Cl H2 C CH2Br (B) CH3Br > CH3CH2Br > (CH3)2CHBr

> >

(C) CH3CH2Cl > CH3CH2CH2Cl > (D) (CH3)3CBr > (CH3)2CHBr > CH3CH2CH2Br
CH3Cl
7. The correct order of boiling point is
(A) CH3 I  CH3 Br  CH3 Cl  CH3 F (B) CH3 Br  CH3 I  CH3 Cl  CH3 F
(C) CH3 F  CH3 Cl  CH3 Br  CH3 I (D) CH3Cl  CH3 F  CH3 I  CH3 Br

8. Cl2
C6H5 CH3  NBS / CCl4
  A   
 B  
  C 
i Mg / ether
Fe
(ii)
O
(iii) H 3O
The structure of (C) is
(A) CH2 CH2 CH2 OH (B) CH2CH2CH 2OH (C) HC CH2 (D) CH2CH2 OH

O
Cl H3C Cl Cl
 QUIZ (CHEMISTRY)
9. The major product of the following reaction is
Me Br

F
PhS Na

dim ethylformamide


NO2
(A) Me SPh (B) Me SPh (C) Me Br (D) Me SPh

F F SPh SPh

NO2 NO2
NO2 NO2

10. H3C CH3 CH3 CH3

O NO2 compound on hydrolysis in aqueous acetone will give

H Cl CH3

(i) H3C CH3 CH3 CH3 (ii) H3C CH3 CH3 CH3

O NO2 O NO2

H OH CH3 OH H CH3

(iii) H3C CH3 CH3 CH3

O NO 2

H CH3 OH
(A) Mixture of (i) and (ii) (B) Only (i) (C) Mixture of (ii) and (iii) (D) Only (iii)
11. The correct nucleophilicity order for SN2 reaction in protic solvent is
(A) CH3 S  C6H5 S   CN  CH3 CH2 O  OH (B) CH3 CH2 O   C6H5 S  CN  CH3 S  OH
(C) CN  CH3 S  C6H5 S  OH  CH3 CH2 O  (D) OH  CH3 S   CN  CH3 CH2 O  C6 H5 S
12. Chlorobenzene is less reactive than benzyl chloride towards nucleophilic substitution is not due to:
(A) The carbon of C – Cl bond in C6H5Cl is sp2 hybridized and holds the electron pair more firmly
as compared to sp3 carbon containing chlorine in C6H5CH2Cl
(B) The C – Cl bond in C6H5Cl is less polar compared to that in C6H5CH2Cl
(C) The C – Cl bond in C6H5Cl acquires partial double bond character due to resonance involving
the lone pair on chlorine atom.
(D) The chlorine in C6H5Cl is deactivating due to its high electronegativity
13. What are reactant ‘X’ and product ‘Y’ in the following sequence of reactions?
O
Me S Cl O
O Me O S Me NaN3
 Product  Y 
Reactant  X  
Pyridine
 ethanol water

H H O
Reactant (X) Product (Y)
(A) Me OH Me N3
H H H H
(B) Me OH Me H
H H H N3
(C) Me H Me H
H OH H N3
(D) Me H Me N3
H OH H H
14. CH3
NaOCH3

CH3 OH
 Product; product of the reaction is:
E2 reaction
Br
CH3
(A) (B) (C) (D) No reaction

OCH3
 QUIZ (CHEMISTRY)
15. OH

conc. H2SO4
 
 A
Major 

Major product (A) is:

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

16. CH3
h
 Cl2  X Number of monohalogen derivative including stereo isomers, the value of X is

(A) 6 (B) 4
(C) 2 (D) 3
14
C labelled
OTs
17. RCO
 2H
 product; Product of this reaction
no label
OCOR OCOR
(A) (B)
(C) both (A) and (B) (D) none of these

18. Which of the following statements is correct regarding the rate of hydrolysis of the compounds (P)
and (Q) by SN1 reaction:
Br
O Br
(P)
(Q)
(A) (P) reacts faster than (Q) (B) (Q) reacts faster than (P)
(C) Both (P) and (Q) reacts at the same rate (D) Neither (P) nor (Q) reacts
Br
Hc Alc KOH
19. + HBr . Which H will get eliminated?
Hb
Ha
(A) Ha (B) Hb (C) Hc (D) none of these

20. Which of the following compounds would react faster with NaCN in an S N 2 reaction?
OMe
OTs OTs
(A) (B) (C) MeO (D)

21. Br Product (A) is:

1eq NaCN
 (A)

Br

CN Br Br CN
(A) (B) (C) (D)

Br CN CN CN

22. When chlorobenzene is treated with NaNH2 in liq NH3, besides aniline, the other by a product that
could be formed
NH–NH2 NH2
(A) (B) (C) –NH–NH– (D)

NH2
 QUIZ (CHEMISTRY)
23. Consider the following anions.
O O O
O–
– –
CF3–S–O C6H5–S–O CH3–C–O–
O O
(I) (II) (III) (IV)
When attached to sp3-hybridized carbon, their leaving group ability in nucleophilic substitution
reaction decreases in the order
(A) I > II > III > IV (B) I > II > IV > III (C) IV > I > II > III (D) IV > III > II > I

24. Among the given pairs, in which pair first compound reacts faster than second compound in SN2
reaction?
CH3 CH3
(A) CH3CH2CH2CH2–Br or CH3–CH2–CH–CH3 (B) CH3–C–CH2CH3 or CH3–CH–CH
Br Br Br CH3
Br Br
CH3 CH3
(C) or (D) CH3–C–CH3 or CH3–C–CH3
Br I

Cl
alc. NBS alc. NBS alc.
25. (A) (B) (C) (D) (E) The product E is
KOH KOH KOH
Br
Br
(A) (B) (C) (D)

26. Which of the following is most reactive towards SN2 reaction?

CH2Cl
CH2–Cl CH2–Cl
CH2Cl
(A) (B) (C) (D)

CH3 Cl NO2

27. The deceasing order of reactivity towards aromatic nucleophilic substitution

Br Br Br Br
O2N NO2 NO2
, , ,
NO2
NO2 NO2 NO2
I II III IV
(A) I > II > III > IV (B) III > II > I > IV (C) II > III > I > IV (D) II > III > IV > I
NO2 Cl
CH2
28.   Product (P) (major)
Na
OC2
H 5 (1eq )
 
( monosubsti tution )
Cl
Cl
NO2 NO2
NO2
CH2Cl CH2OC2H5
(A) CH2Cl (B) (C) (D) none of these
Cl H5C2O Cl
OC2H5 Cl Cl

O 
OH (1 eq )
29. Cl– –CH2–C– –Cl   (P) major
mono
substituti on
O2N NO2
O O O
(A) (B) (C) (D) none of these
HO– –CH2–C– –Cl Cl– –CH2–C– –OH Cl– –CH–C– –Cl
OH
O2N NO2 O2N NO2 NO2 NO2
 QUIZ (CHEMISTRY)
30. C2H5ONa+ (P).
Br 

Major product (P) would be

(A) (B) (C) (D) both (B) and (C)

OEt


QUIZ (CHEMISTRY)
ANSWERS
ALKYL HALIDE & ARYL HALIDE
1. B 2. A 3. A 4. A

5. B 6. B 7. A 8. A

9. A 10. A 11. A 12. D

13. B 14. D 15. C 16. A

17. C 18. B 19. A 20. D

21. A 22. B 23. B 24. A

25. C 26. D 27. D 28. C

29. B 30. B