SRI VIJAY VIDYALAYA COLLEGE OF ARTS & SCIENCE,

NALLAMPALLI
Accredited with ‘A’ grade by NAAC
M.Sc. ORGANIC CHEMISTRY –I
UNIT -IV
Electrophillic Substitution Reactions
1. Which of the following is rate determining step in electrophilic substitution reaction?
a) Generation of electrophile b) Attack by an electrophilic reagent on benzene ring
c) Formation of product d) All of the mentioned

2. Which of the following act as a catalysis in the nitration of benzene?

a) Conc. HCl b) Dil. HCl c) Conc. H2SO4 d) Dil. H2SO4
3. Fuming sulphuric acid is the solution of _________% SO3 in conc. H2SO4.
a) 10 b) 9 c) 8 d) 7

4. Which of the following is the necessary condition for desulphonation?

a) Remove volatile hydrocarbon by steam distillation
b) Low concentration of water
c) High concentration of sulphonating agent
d) A large excess of fuming sulphuric acid

5. Which of the following act as electrophile in halogenation?

a) Nitronium ion b) Sulphonium ion c) Halonium ion d) Acylium ion

6. Aromatic bromination catalyzed by the Lewis acid thalium acetate gives

a) Para isomer b) Ortho isomer c) Meta isomer d) Para and ortho isomer

7. The reaction in which benzene reacts with alkyl halide in presence of a lewis acid as a
catalyst to produce alkylbenzene is known as
a) Nitration b) Halogenation c) Friedel-Crafts Acylation d) Friedel-Crafts Alkylation

8. Which of the following is not a product of the reaction of benzene with CH3Cl and AlCl3?
a) Toulene b) Isopropyl benzene c) O-xylene d) P-xylene
9. The product of Friedel-Crafts Acylation reactions are
a) Alkylbenzene b) Alkylamine c) Arylketone d) Halobenzene

10. How will you convert benzene into n-propyl benzene?

a) Friedel-Crafts Alkylation b) Friedel-Crafts Acylation
c) Friedel-Crafts Alkylation followed by clemmensen reduction
d) Friedel-Crafts Acylation followed by clemmensen reduction

11.An activating substituent group activates

a) Ortho position b) Para position c) Both ortho and para positions d) Meta position
12.A deactivating substituent group directs
a) Ortho position b) Para position
c) Both ortho and para positions d) Meta position

13. Which of the following is ortho-para directing group?

a) –NHCOCH3 b) –NO2 c) –CN d) –CHO

14. Which of the following is meta directing group?

a) –NHCOCH3 b) –COOH c) –OH d) –OCH3

15. The most stable carbonium ion is

a) Methyl carbonium ion b) 20 carbonium ion
c) 10 carbonium ion d) 30 carbonium ion

16. Which of the following has the highest activation of benzene ring?
a) – NHCOCH3 b) –OH c) –NH2 d) –C6H5

17. HBr reacts fastest with

a) 2-methylpropan-2-ol b) Propan-1-ol c) Propan-2-ol d) 2-methylpropan-1-ol

18. The compound that can be most readily sulphonated is

a) Benzene b) Nitrobenzene c) Toluene d) Chlorobenzene

19. In Cannizaro reaction, two molecules of aldehydes are reacted to produce

a) Alcohol only b) Carboxylic acid only
c) Alcohol and carboxylic acid d) Alcohol, carboxylic acid and ketone
20, With respect to the electrophilic aromatic substitution of benzene which of the following
is not true?
a) A non-aromatic intermediate is formed b) Benzene acts as an electrophile
c) A proton is lost in the final step d) Resonance forms are important

2 1.In the body many mono-substituted aromatic compounds are metabolised...

a) To the para-fluoro compound which may be prevented by the addition of a para-hydroxy
group
b) By G-protein coupled receptors
c) To less polar compounds
d) To the para-hydroxy compound which may be prevented by the addition of a para-
fluoride
22 Which of the following statements is incorrect: aromatic compounds...
a) Are planar b) Have 4n π-electrons c) Are cyclic
 d) Are generally less reactive than similarly substituted alkene
23 When considering electrophilic aromatic substitution reactions electron withdrawing
substituents (e.g. nitro) are described as...
a) Ortho/para directing and activating b) Ortho/para directing and deactivating
c) Meta directing and activating d) Meta directing and deactivating
24 The Friedel-Crafts alkylation...
a) Works very well for primary chlorides b) Works very well for tertiary chlorides

c) Works very well for acyl chlorides d) Works very well without a catalyst

25 Salbutamol is an effective treatment for asthma; which of the following

statements is not true:
a) It can be synthesised from aspirin b) It is active at the β2-adrenorecptor

c) It has a shorter duration of action than adrenaline d) The (R)-stereoisomer is the

more active

26 When considering electrophilic aromatic substitution reactions the halides are

described as...
a) Ortho/para directing and activating b) Ortho/para directing and deactivating

c) Meta directing and activating d) Meta directing and deactivating

27 When considering electrophilic aromatic substitution reactions electron

donating subsituents (e.g. methoxy) are described as:
a) Ortho/para directing and activating b) Ortho/para directing and deactivating

c) Meta directing and activating d) Meta directing and deactivating

28 With respect to the electrophilic aromatic substitution of benzene which of the

following is not true:
a) A non-aromatic intermediate is formed b) Benzene acts as an electrophile

c) A proton is lost in the final step d) Resonance forms are important

29 Which of the following drugs does not contain an aromatic species? You should
use this opportunity to get some background on the well known drugs listed.
a) Salbutamol b) Imatinib c) Valsartan d) Pregabalin

30 Which of the following is not associated with electrophilic aromatic substitution?

 a) The formation of nitrobenzene b) The formation of benzyne
c) The formation of bromobenzene d) The formation of benzene sulfonic acid

31Which is most reactive in electrophilic substitution?

a) b)

c) d)

32 Which is least reactive in electrophilic substitution?

a) b)

c) d)

33 Which gives a meta nitro compound as the main product upon nitration with a
nitric acid-sulfuric acid mixture?

a) b)

c) d)
34 Which is most reactive in electrophilic substitution?

a) b) c) d)

35 Which is least reactive in electrophilic substitution?

a) b) c) d)

36 Which gives a meta nitro compound as the main product upon nitration with a nitric acid-
sulfuric acid mixture?

a) b) c) d)

37 Which will be the main product upon chlorination of m-nitrotoluene with

Cl2/AlCl3?

a) b)

c) d)

38 Which is obtained as the main mononitration product upon reaction of m-t-

butylanisole (1-t-butyl-3-methoxybenzene) with HNO3-H2SO4?

a) b)
 c) d)

39 Which of the following statements regarding Friedel-Crafts reactions is wrong?

a) Alkylation of benzene with an alkyl chloride requires only a catalytic amount of a Lewis
acid such as aluminum chloride.
b) Alkylation of benzene with an alcohol requires only a catalytic amount of a Brønsted acid
such as phosphoric acid.
c) Acetylation of benzene with acetyl chloride requires only a catalytic amount of a Lewis
acid.
d) Acetylation of benzene with acetic anhydride requires more than one equivalent of a
Lewis acid.
40 Which of the following statements regarding electrophilic aromatic substitution is wrong?
a) Acetyl and cyano substituents are both deactivating and m-directing.
b) Alkyl groups are activating and o,p-directing.
c) Ammonio groups are m-directing but amino groups are and o,p-directing.
d) Chloro and methoxy substituents are both deactivating and o,p-directing.
41 Which is most reactive in electrophilic substitution?

a) b) c) d)

42 Which is least reactive in electrophilic substitution?

a) b) c) d)

43 Which gives a para nitro compound as the main product upon nitration with a nitric acid-
sulfuric acid mixture?

a) b)
 c) d)

44 Which gives a meta nitro compound as the main product upon nitration with a nitric acid-
sulfuric acid mixture?

a) b)

c) d)

45 Which of (a)-(d) does not give isopropylbenzene as a product upon reaction with benzene?
a) (CH3)2CHCl/AlCl3 b) CH3CH2CH2Cl/AlCl3
c) CH3CH=CH2/H3PO4 d) (CH3)2C=CH2/H3PO4
46 Which combination of reagents used in the indicated order with benzene will give m-
nitropropylbenzene?
a) 1) HNO3/H2SO4, 2) CH3CH2CH2Cl/AlCl3 b) 1) CH3CH2CH2Cl/AlCl3, 2) HNO3/H2SO4
c) 1) CH3CH2COCl/AlCl3, 2) HNO3/H2SO4, 3) H2NNH2/NaOH d) 1) HNO3/H2SO4, 2)
CH3CH2COCl/AlCl3, 3) H2NNH2/NaOH
47 Which pair of compounds are the most probable main products of the following reaction?

a)
 b)

c)

d)

48 Which pair of compounds are the most probable main products of the following reaction?

a)

b)
 c)

d)

49 Which will be the main product upon bromination of phenyl benzoate with Br2/AlBr3?

a) b)

c) d)

50 Which of the following statements regarding electrophilic aromatic substitution is wrong?

a) Sulfonation of toluene is reversible.
b) Friedel-Crafts alkylation of benzene can be reversible.
c) Friedel-Crafts alkylation with primary alkyl chloride may involve rearrangement.
d) Friedel-Crafts acylation of nitrobenzene readily gives a meta substitution product.
UNIT- IV ANSWER KEY ( PG ORGNANIC –I)

1 B 11 C 21 C 31 B 41 D

2 C 12 D 22 B 32 C 42 B
3 D 13 A 23 D 33 C 43 B
4 B 14 B 24 B 34 D 44 D
5 C 15 D 25 C 35 B 45 D
6 D 16 B 26 B 36 B 46 A
7 D 17 A 27 A 37 A 47 A
8 D 18 C 28 B 38 B 48 C
9 C 19 C 29 D 39 D 49 A
10 A 20 B 30 B 40 D 50 D