Exercise - III Subjective Level-I: C - CL HC CHCH

Page # 28 AROMATIC COMPOUNDSE
Exercise - III Subjective Level-I
1. What product is formed when 2-

methylpropene is added to a large excess of
benzene containing HF and the Lewis acid BF3? H3C CH 2CH2 – C – Cl
By what mechanism is it formed?
2. Predict the product of the following reaction

and give the curved-arrow mechanism for its 6. Predict the product(s) of
formation. (Hint: Friedel-Crafts alkylations can (A) Friedel-Crafts acylation of anisole
be used to form rings.) (methoxybenzene) with acetyl chloride in the
presence of one equivalent of AlCl3 follwed by
H2O.
H3C CH2CH2CH2 – Cl
AlCl
 3  (B) Friedel-Crafts alkylation of a large excess
of ethylbenzene with chloromethane in the
(a compound C10H12+HCl) presence of AlCl3.
3. Give the structure of the product expected 7. Biphenyl (phenylbenzene) undergoes the
from the reaction of each of the following com- Friedel-Crafts acylation reaction, as shown by
pounds with benzene in the presence of one the follwoing example.
equivalent of AlCl3, followed by treatment with
water. + Cl – C – CH 3
1)AlCl3
C – CH3 + HCl
2)H2O
biphenyl
(A) (CH3)2CH – C – Cl
p-phenylacetophenone
On the basis of this result, what is the direct-
ing effect of the phenyl group ?
(B) C – Cl
8. Predict the predominant products that would
lsobutyryl chloride result from bromination of each of the follow-
ing compounds. Classify each substituent group
benzoyl chloride as an ortho, para director or a meta director.
and explain your reasoning
4. Show two different Friedel-Crafts acylation
reactions that can be used to prepare the ..
following compound. (A) NH – C – CH3
CH3
(B) CF3
C CH 3
+
(C) N(CH3)3
CH3
5. The following compound reacts with AlCl3 fol- (D) C(CH3)3

lowed by water to give a ketone A with the
formula C10H10O. Give the structure of A and a
..
curved -arrow mechanism for its formation
(E) O
..
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AROMATIC COMPOUNDS Page # 29
9. Explain why the nitration of anisole is much 14. When the following compound is treated with
faster than the nitration of thioanisole under H2SO4 the product of the resulting reaction
the same conditions. has the formula C15H20 and does decolorize Br2
.. in CCl4. Suggest a structure for this product
OCH3
.. and give a curved - arrow mechanism for its
formation.
..
SCH
.. 3
OH
CH3
anisole thioanisole
H2SO 4
?
10. Which should be faster bromination of ben-
zene or bromination of N,N - dimethylaniline?
Explain your answer carefully.
15. Write the principal organic product in each of
the following reactions:
..
N (CH3)2 Cl
NO2
N,N - dimethylaniline
11. Outline a synthesis of m-nitroacetophenone (i) + C6H5 CH2SK A

from benzene: explain your reasoning.
CH3
Cl
C – CH3
NO2
(ii) H
2 NNH 2
 B
NO2 triethylen e
glycol
NO2
12. Give the products expected(if any) when
ethylbenzene reacts under the following con-
ditions.
(A) Br2 in CCl4 (dark)
CF3
(B) HNO3 ,H2SO4
(C) conc. H2SO4
(D) C2H5 – C – Cl,AlCl3(1.1 equiv.) then H2O (iii) ( i ) HNO 3 , H 2SO 4
  C
( ii ) NaOCH , CH OH
3 3
(E) CH3Br,AlCl3
(F) Br2,FeBr3 Cl
13. Give the products expected (if any) when ni- Cl NH 2

trobenzene reacts under the following condi-
tions.
(A) Cl2,FeCl3, heat
(B) fuming HNO3,H2SO4 (iv) (
i ) NaNO 2 , HBr
  D
( ii ) CuBr
(C) H3C – C – Cl,AlCl3(1.1 equiv.) then H2O
dichloride
isomers with formula C15H12O2)
(v) Br OCH3
(D) + HNO3 H
2SO 4

0 C
CH3
(i) NBS,Benzoylperoxide,CCl4 .heat
 E
(ii) NaSCH 3
Cl
(E) ferrocene + H 3C – C – Cl 1
) AlCl 3

2 ) H 2O
NO2 (C12H12OFe)
(vi) + CH3CH2ONa F (F) CH3O SO3H HNO3 Br2,Fe
NO2 OH
Cl Br2
17.  Product A and B is
H 2O
NO2
(vii) + C6H5CH2SNa  G
Br2
B
NO2 CS2
16. Complete the following reactions?

(A) benzene (large excess) l3
/ AlC A
Cl 2
+ClCH2 CH2Cl AlCl
 3  18. Cl
2 /
hv
B
Product A and B is
O – CH 2CH 2CH – Cl
(B) AlCl
 3  Exercise-IV (Matrix)
CH 3
1. Substituent on phenyl ring.
(a compound with ten carbons)
(A) – CH2 – CH3
(P) o/p - directors
Cl – C – C – C – Cl
(C) +
(B) – O – S – CH3 (Q) meta directors
H3 C CH3
1
) AlCl 3
 (three products, all
2 ) H 2O (C) – NH – C – CH3 (R) Activating group
naphthalene
-dimethylmalonyl (D) – S – CH3 (S) Deactivating group
2. Column I
(A) CO2 is evolved from O – CH = CH2
(B) Libbermann nitroso test is given by
(C) Compounds gives yellow oily
(D) When reacts with CHCl

 
3
 (C) (R) o/p director
HO
Column II
O–H
S – Et
(P)
(D) (S) meta- director
NaHCO3 by the reaction of

CO2H 4. Column I Column II
(A) Cl (P) Group attached to
benzene ring is a + M
(Q) group here
(R) R – NH – R
liquid on reaction with NaNO2 + HCl
CH3
S (B) (Q) Group attached to

(S) Ph – – OH
benzene ring is a – M
group here
salicy ladehyde will form

(R) Electropile would
3. Compounds attack on ortho or para
(C) position
Substituent on phenyl N
S –Et
(A) (P) Activating group

(D) (S) Rate of electrophilic
substitution is less than
that of bnzene
5. Match th column :
X OCH3
(B) (Q) Deactivating group

CH
3ONa



NO2 NO2
X = halogen
relative reactivity toward (SNAr) OH
(A)– F (P) 312
(B) – Cl (Q) 1 
(C) – Br (R) 0.8 (R) (

i ) CHCl 3 / HO
 

( ii ) H
(D) – I (S) – 1
6. Matrix : Reaction
Product Ph OH
(S) C=N PCl
5 
CH3
F
carbon increases
CHCl3 8. Column-I Column-II (Reagent used)

(A)  
KOH,
OH OH
CHO
Cl (A)
(B) CHFCIBr
 
KOH ,  + –
NH 2 NC
(B)
Br
(C) CHCI
 2 Br

KOH , 
NH 2
(C) Ph—NH2
(D) CHBr
 2 CI
 
KOH , 
N – OH
7. Column-I
(A) Caprolactum formation take place in
(D) Ph – C – Ph Ph – C – NH – Ph
(B) Beckmann rearrangement is
(C) Schmidt reaction is
(D) Reaction in which number of Column-II
Column-II (P) CHCl3 / KOH
(Q) Br2 / KOH
(R) H2SO4
(S) PCl5
(P) HN
3  9. Matrix
H 2SO 4 Column-I
N – OH (A) HNO
3 
H 2SO 4

H
(Q) 

11. Which of the following synthesis could be done

Cl in the single step ?
(B)
AlCl3 OH OH
OH
Br2 (A)
(C)  
H 2O
CH3 Br
Br2 OH OH
(D) 
Fe
Br Br
Column - ll
(P) Carbocation is intermediate (B)
(Q) Carabanion is intermediate
(R) Electrophilic substitution reaction CH3 Br
(S) Rearrangement takes place
10. Column-I
OH OH
Br
(A) + CO + HCl AlCl
 3  (C)
(B) Ph – C = N SnCl
 2 / HCl

H 2O
NH2 NH2
CH3
CrO 2 Cl2
(C)  
H 2O
(D)

CH3 Br
(D) Ph – C  N H 3O

Column-II 12. Which of following is the incorrect major prod-
(P) Ph – CHO is product uct ?
(Q) Etard reaction
(R) Stephon reduction OCH3 OCH3 CH3
(S) Gattermann Koch reaction
(T) Ph – CO2H
CH3
Comprehension - 3 (11 to 13) ( CH 3 ) 2 CHBr
(A)   

It is not always easy to predict the position of AlCl3 ,15 25 C
attack on multiply substituted benzene. If the
benzene ring bears different group ortho/ para CH3 CH3
directing group at the 1 and 4 positions, the
position of further substitution is not immedi-
ately clear.
(B)
CH3 CH3
CH3
CH3 – C – Cl
AlCl3,CS 25°C
H3C CH3 H3C CH3
(C)
NH2 NH2
Br Br
OH Br H 2O
2 
40 , 50 C
Br OH
OH
OH Br Br
Br2
(D) 
CS 2 , 0 C
Br
13. Which of the following side chain reaction/s

can be used to reduce the activity of strongly
activating groups like – OH
(A) benzoylation
Ph – C –
(B) acetylation CH3 – C –
(C) both of the above

(D) none of the above
Exercise - V Subjective Type

9. Arrange in order of decreasing trend towards
1. Among the following the compound that can
SE reactions: [JEE 1995]
be most readily sulphonated is [JEE 1982]
(I) Chlorobenzene (II) Benzene
(A) Benzene (B) Nitrobenzene
(III)Anilinium chloride(IV) Toluene
(C) Toluene (D) Chlorobenzene
(A) II > I > III > IV (B) III > I > II > IV
(C) IV > II > I > III (D) I > II > III > IV
2. What phenol is treated with excess of bromine
water. it gives [JEE 1984]
10. When phenol is reacted with CHCl3 and NaOH
(A) m-bromophenol
followed by acidification, salicyladehyde is
(B) o-andp-bromophenol
formed. Which of the following species are in-
(C) 2,4-dibromophenol
volved in the above mentioned reaction as in-
(D) 2,4,6- tribromophenol
termediates ? [JEE 1995]
3. Chlorobenzene can be prepared by reacting OH
aniline with [JEE 1984]
(A) Hydrochloric acid H CHCl2
(B) Cuprous chloride
(A) CCl2 (B)
(C) Chlorine in presence of anhyd AlCl3
(D) Nitrous acid followed by heating with cu-
prous chloride
4. The compound that is most reactive towards

electrophilic substitution is[JEE 1985]
H CHCl2
(A) Toluene (B) Benzene
(C) Benzoic acid (D) Nitrobenzene (C) CHCl (D)
5. The chlorination of toluene in presence of fer- OH

ric chloride gives predominantly
[JEE 1986]
(A) Benzyl chloride 11. Among the following statements on the nitra-
(B) m- chlorotoluene tion of aromatic compounds the false one is :
(C) Benzal chloride [JEE 1997]
(D) o-and p-chlorotoluene (A) The reate of benzene is almost the same
as that of hexadeuterobenzene
(B) The rate of nitration of toluene is greater
6. Phenol reacts with bromine in carbon disulphide than of benzene.
at low temperature to give[JEE 1988] (C) The rate of nitration of benzene is greaer
(A) m-bromophenol than that of hexadeuterobenzene
(B) o-and p- bromophenol (D) Nitration is an electrophilic substitution
(C) p-bromophenol reaction
(D) 2,4,6 - tribromophenol
12. Nitrobenzene can be prepared from benzene
7. The most basic compound among the follow- by using a mixture of conc. HNO 3 and
ing is: [JEE 1990] conc.H2SO4. In the nitrating mixture HNO3 acts
(A) Benzylamine (B) Aniline as a [JEE 1997]
(C) Acetaniline (D) p-nitro aniline (A) Base (B) Acid
(C) Reducing agent (D) Catalyst
8. Most stable carbonium ion is:[JEE 1995]
+ 13. In the reaction of p- chlorotoluene with KNH2
(A) p – NO2 – C6H4 – CH 2 in liq. NH3 the major product is
+ [JEE 1997]
(B) C6H5 CH2
(A) o-toluidine (B) m - toluidine
+
(C) p – Cl – C6H4 – CH 2 (C) p-toluidine (D) p-chloro aniline
(D) p – CH3O – C6H4 – +CH2
14. Benzene diazonium chloride on reaction with

phenol in weakly basic medium gives CH3
[JEE 1998]
(A) Diphenyl ether
(B) p-hydroxy azobenzene (I) (II)
(C) Chlorobenzene
(D) Benzene
15. A solution of (+) -2 chloro-2 phenylethane in Cl NO2

tolune recemises slowly in the presence of small
amount of SbCl5 due to the formation of
[JEE 1999]
(III) (IV)
(A) Carbanion (B) Carbene
(C) Free - radical (D) Carbocation
16. Statement -1 Phenol is more reactive than (A) I>II>III>IV (B) IV>III>II>I
benzene towards electrophilic substitution re- (C) II>I>III>IV (D) II>III>I>IV
action.
Statement -2 In the case of phenol the inter-
mediate carboation is more resonance stabi-
lized. 20. F NO2 (
CH 3 ) 2 NH
 A
DMF
(A) Statement -1 is true Statement -2 is true
and Statement -2 is correct explanation for (i) NaNO 2 HCl 0 5 C
Statement -1
  B [JEE 2003]
(ii) H 2 Catalytic Re duction
(B) Statement -1 is true Statement -2 is true
and Statement -2 is not correct explanation
for Statement -1 (A) O2N NH2
(C) Statement -1 is true Statement -2 is false
(D) Statement -1 is false Statement -2 is true
[JEE 2000] H3C
(B) N NH 2
17. Amongst the following the strongest base is H3 C
[JEE 2000]
(A) C6H5NH2 (B) p-O2NC6H4NH2 H 2C
(C) m-O2NC6H4NH2 (D) C6H5CH2NH2
N NO2
18. Statement -1 : In strongly acidic solutions, H 2C
aniline becomes more reactive towards elec- (C)
trophilic reagents [JEE 1982]
NH2
Statement -1 : The amino group being com-
pletely protonated in strongly acidic solution,
H 3C
the lone pair of electrons of the nitrogen is no
longer available for resonance. (D) N NO2
(A) Statement -1 is true Statement -2 is true H 3C
and Statement -2 is correct explanation for
Statement -1
(B) Statement -1 is true Statement -2 is true
and Statement -2 is not the correct explana- NH
tion for Statement -1 Me Me
(C) Statement -1 is true Statement -2 is false
(D) Statement -1 is false Statement -2 is true 21.
19. ldentify the correct order of reactivity in elec-

trophilic substitution reactions of the follow- Br2
ing compunds : [JEE 2002] 
Fe
Major product of above reaction is:
[JEE 2004]
NH
23. + Cl – CH 2CH 2 – CH 3 AlCl
 3  P
Me Me
(A) ( i)O2 / 

 Q + Phenol P and Q are respec-
( ii ) H 3O 
tively [JEE 2006]
Br
(A) + CH3CH2CHO
NH
Me Me
(B) + CH3COCH3
(B)
Br
(C) + CH3COCH3
NH
Me Me
(C)
Br (D) + CH3CH2CHO
NH
Comprehension Type : (Q.24 to Q.26)
Me Me Reimer -Tiemann reaction introduces an alde-
hyde group on to the aromatic ring of phenol,
ortho to the hydroxyl group. This reaction in-
(D)
volves electrophilic aromatic substitution. This
is a general method for the synthesis of sub-
Br stituted salicyladehydes as depicted below.
[JEE 2007]
OH
22. Which of the following is obtained when 4-
Methylbenzenesulphonic acid is hydrolysed with
excess of sodium acetate ? [JEE 2005]
–+
(A) CH3 COONa I 

CH3
(B) CH3 + SO3
ONa OH
–+ CHO CHO
(C) CH3 SO3Na + CH3COOH
aq.HCl

(D) CH3 SO2O.COCH3 + NaOH
CH3 CH3
(I) (II) (III)
24. Which one of the following reagents is used in

the above reaction?
(A) aq NaOH + CH3Cl O2N
(B) aq NaOH + CH2Cl2
(C) aq NaOH + CHCl3 N

(B)
(D) aq NaOH + CCl4 H
25. The electrophile in this reaction is

(A) :CHCl (B) CHCl2+
(C) :CCl2 (D) CCl3
26. The structure of the intermediate I is N

(C) H
NO2
ONa ONa
CH2Cl CHCl2
(A) (B) N
(D) O2N
H
CH3 CH3
ONa ONa 28. Statement-1: p- Hydroxybenzoic acid has a

lower boiling point than o- hydroxybenzoic acid.
CCl3 CH2OH [JEE 2007]
Statement-2: o-Hydroxybenzoic acid has in-
tramolecular hydrogen bonding.
(C) (D) (A) Statement-1 is True Statement-2 is True
Statement-2 is a correct explanation for State-
CH3 CH3 ment-1
(B) Statement-1 is True Statement-2 is True
Statement-2 is Not explanation for Statement-
27. In the following reaction 1
(C) Statement-1 is True Statement-2 is False
(D) Statement-1 is False Statement-2 is True
29. Statement-1: Bromobenzene upon reaction

.. with Br2 / Fe gives 1,4-dibromobenzene as the
N major product. [JEE 2008]
H Statement-2: in bromobenzene the inductive
effect of the bromo group is more dominant
than the mesomeric effect in directing the in-
coming electrophile.
con. HNO 3
X (A) Statement-1 is True Statement-2 is True
con. H2SO 4 Statement-2 is a correct explanation for State-
the structure of the major product ‘X’ is ment-1
(B) Statement-1 is True Statement-2 is True
Statement-2 is Not explanation for Statement-
1
NO2 (C) Statement-1 is True Statement-2 is False
(A) N (D) Statement-1 is False Statement-2 is True
H
30. Statement-1 : Aniline on reaction with NaNO2

/HCl at 0°C followed by coupling with
 - naphthol gives a dark blue coloured pre-
cipitate. [JEE 2008] C
Statement-2 : The colour of the compound
formed in the reaction of aniline with NaNO2 /
HCl at 0° followed by coupling with  naph- O2N
thol is due to the extended conjugation.
(A) Statement-1 is True Statement-2 is True
Statement-2 is a correct explanation for State-
ment-1 OCH3
(B) Statement-1 is True Statement-2 is True COOH
Statement-2 is not explanation for Statement-
1 (B) H 3C
(C) Statement-1 is True Statement-2 is False
HO NO2
(D) Statement-1 is False Statement-2 is True NO2
31. The compounds P,Q and S [JEE 2010]

C
COOH
NO2
(P)
HO COOH
OCH3
(Q) (C) HO
H3C
NO2
OCH3
C
(S)
H3C NO2
were separately subjected to nitration using NO2

HNO3 / H2SO4 mixture.The major product formed
in each case respectively is
C
COOH OCH3
(A) HO H3C
COOH
NO2 NO2
(D) HO
NO2
34. A new carbon - carbon bond formation is pos-

sible in [JEE 1998]
(A) wolf-kishner reduction
C (B) Friedel-Craft alkylation
(C) Clemmensen reduction
NO2
(D) Reimer-Tiemann reaction
O2N 35. An aromatic molecule will

[JEE 1999]
(A) have 4n  -electrons
32. Amongst the compounds given the one the
(B) have (4n+2)  -electrons
would form a brilliant colored dye on treat- (C) be planar
ment with NaNO2 in dil. HCl followed by addi- (D) be cyclic
tion to an alkaline solution of  - naphthol is
[JEE 2011]
36. Toluene when treated with Br 2/Fe gives p-
bromotoluene as the major product because
N(CH3)2 the CH3 group: [JEE 1999]
(A) ortho para directing
(B) is meta directing
(A)
(C) activates the ring by hyperconjugation
(D) deactivates the ring
NHCH3
OH
(B)
37. In the reaction NaOH

 ( aq
) / Br2
 the in-
NH2
(C) termediate (s) is (are) [JEE 2010]

H 3C
OO
O
CH 2NH 2
Br
(D)
(A) (B)
Multiple Choice Question: Br Br

Br
33. When nitrobenzene is treated with Br 2 in
presenceof FeBr3 the major product formed is OO
m - bromonitrobenzene.[JEE 1992] OO
Statements which are related obtain the m-
isomer are.
(A) The electron density on meta carbon is
more than on ortho and para position. (C) (D)
(B) The intermediate carbonium ion formed af-
ter initial attack of Br+ attack the meta posi- Br
Br
tion is least destabilized
(C) Loss of aromaticity when Br+ attacks at
the ortho and para positions and not at meta
position.
(D) Easier loss of H+ to region aromaticity form
the meta position than from ortho and para
position.

Exercise - III Subjective Level-I: C - CL HC CHCH

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Page # 28 AROMATIC COMPOUNDSE

Exercise - III Subjective Level-I

1. What product is formed when 2-

2. Predict the product of the following reaction

5. The following compound reacts with AlCl3 fol- (D) C(CH3)3

11. Outline a synthesis of m-nitroacetophenone (i) + C6H5 CH2SK A

13. Give the products expected (if any) when ni- Cl NH 2

(C) H3C – C – Cl,AlCl3(1.1 equiv.) then H2O

(vi) + CH3CH2ONa F (F) CH3O SO3H HNO3 Br2,Fe

16. Complete the following reactions?

(D) When reacts with CHCl

NaHCO3 by the reaction of

S (B) (Q) Group attached to

salicy ladehyde will form

(A) (P) Activating group

(B) (Q) Deactivating group

(C) – Br (R) 0.8 (R) (

CHCl3 8. Column-I Column-II (Reagent used)

11. Which of the following synthesis could be done

13. Which of the following side chain reaction/s

(B) acetylation CH3 – C –

(C) both of the above

Exercise - V Subjective Type

4. The compound that is most reactive towards

5. The chlorination of toluene in presence of fer- OH

14. Benzene diazonium chloride on reaction with

15. A solution of (+) -2 chloro-2 phenylethane in Cl NO2

19. ldentify the correct order of reactivity in elec-

(I) (II) (III)

24. Which one of the following reagents is used in

(C) aq NaOH + CHCl3 N

25. The electrophile in this reaction is

(C) :CCl2 (D) CCl3

26. The structure of the intermediate I is N

ONa ONa 28. Statement-1: p- Hydroxybenzoic acid has a

29. Statement-1: Bromobenzene upon reaction

30. Statement-1 : Aniline on reaction with NaNO2

31. The compounds P,Q and S [JEE 2010]

were separately subjected to nitration using NO2

34. A new carbon - carbon bond formation is pos-

O2N 35. An aromatic molecule will

37. In the reaction NaOH

(C) termediate (s) is (are) [JEE 2010]

Multiple Choice Question: Br Br

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