ALLEN® Aromatic Compound 1

AROMATIC COMPOUND 4. ukbVªkscsUthu dks m-MkbczksekscsUthu esa ifjofrZr

djus ds fy, mi;ksx fd;s tkus okys vfHkdeZd
1. fuEufyf[kr vfHkfØ;k esa 'A' rFkk 'B' gS:
NH2 dk lgh Øe D;k gS\
+
NaNO2/HCl SnCl2/HCl/H3O
(A) (B) NO2 Br
KCN
+ –
N2Cl CHO
Br
(1) (A) : (B) : +
(1) ¾¾¾¾
NaNO
® / ¾¾¾
HCl
2
® / ¾¾¾
KBr
® / ¾¾¾
H
®
+ –
N2Cl Cl
(2) ¾¾¾
Br /Fe
® / ¾¾¾®
2 Sn /HCl
/ ¾¾¾¾ ¾
NaNO /HCl
® / ¾¾¾¾
CuBr / HBr
2
®
(2) (A) : (B) : +
(3) ¾¾¾®
Sn / HCl
/ ¾¾¾
KBr
® / ¾¾®
Br
/ ¾¾
H
® 2

CN CHO
(4) ¾¾¾®
Sn / HCl
/ ¾¾®
Br
/ ¾¾¾
NaNO
® / ¾¾¾
2 NaBr
® 2

(3) (A) : (B) :

CN Cl 5. fuEufyf[kr ;kSfxdksa dk] ukfHkd Lusgh izfrLFkkiu

(4) (A) : (B) : vfHkfØ;k ds fy, nj c<+us dk lgh Øe gS %

Cl Cl Cl Cl
2. fuEufyf[kr vfHkfØ;k esa esVk&ukbVªks mRikn ds Hkh NO2 O 2N NO 2
cuus dk dkj.k gS :–
NH2 NH2 NH2 NH2
NO2 NO2 NO2 NO2
Conc.HNO 3
Conc.H2SO4, 288K + + (i) (ii) (iii) (iv)
NO2
NO2
(1) (iv) < (iii) < (ii) < (i)
[A] [B] [C]
51% 47% 2%
(2) (iv) < (i) < (ii) < (iii)
(1) de rkieku
(2) –NH2 xzqi vR;f/kd esVk&funsZ'kh gS (3) (iv) < (i) < (iii) < (ii)

(3) ,sfuyhfu;e vk;u dk fuekZ.k (4) (i) < (ii) < (iii) < (iv)
(4) –NO2 izfrLFkkiu ges'kk esVk&LFkku ij gh 6. fuEufyf[kr esa ls fdldk Mkb,stksfu;e yo.k]
gksrk gS
NaOH esa b-uSQFkkWy ls vfHkfØ;k djds jaxhu
3. fuEufyf[kr esa ls dkSulk ;kSfxd lkUæ H2SO4 esa
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FkSfyd ,ugkbMªkbM ls vfHkfØ;k ds i'pkr~ NaOH jatd cuk;sxk?

ls vfHkfØ;k djds xqykch jax nsrk gS? CH2NH2
CH3 (1)
(1)
OH CH3
HO CH3 N CH3
(2) (2)
HO CH3
H 3C CH3 NH2
(3) (3)
HO OH
CH3 NH–CH3
(4) (4)
HO

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2 Aromatic Compound ALLEN®
7. fuEufyf[kr esa ls dkSu lh vfHkfØ;k 10. fuEufyf[kr vfHkfØ;k dk eq[; mRikn gS :

p-,sehuks,stkscsUthu ugha nsxh?

NO 2

(A) (i) Sn/HCl

(ii) HNO2
(iii) Aniline (1) (2)

NO 2

(B) (i) NaBH4

(3) (4)
(ii) NaOH
(iii) Aniline
11. csUthu ls 4-czkseks-2-ukbVªks,fFky csUthu cukus ds
NH2
fy, iz;ksx esa fy;s x;s vfHkdeZdksa dk lgh Øe gS:
(C) (i) HNO2
(ii) Aniline, HCl
(1) HNO3/H2SO4, Br2/AlCl3, CH3COCl/AlCl3,
Zn-Hg/HCl
(1) dsoy A (2) dsoy B (2) Br2/AlBr3, CH3COCl/AlCl3, HNO3/H2SO4,
(3) dsoy C (4) A rFkk B Zn/HCl
(3) CH3COCl/AlCl3, Br2/AlBr3, HNO3/H2SO4,
8. fuEufyf[kr vfHkfØ;k esa A dks ifgpkfu, %
Zn/HCl
CH3 (4) CH3COCl/AlCl3, Zn-Hg/HCl, Br2/AlBr3,
CH2 HNO3/H2SO4
CH3 Mo2O 3
'A'
CH2 CH 773 K, 10-20 atm major product
12.
CH2 CH3

(1)

(2)

CH3
(3)
nh gq;h jklk;fud vfHkfØ;k ds fy, lgh dFku
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CH3 gS:
(4)
(1) xqzi vkFkkZsa rFkk iSjk funZs'kh gSa vr%
mRikn (B) laHko ugha gSA
9. fuEufyf[kr jklk;fud vfHkfØ;k ij fopkj
(2) vfHkfØ;k laHko gS vkSj ;kSfxd (B) eq[; mRikn
dhft,A
gksxkA
(1) Red hot Fe tube, 873 K (3) ukbVªhdj.k ds LFkku ij vfHkfØ;k lYQksfudr
CH º CH Product
(2) CO, HCl, AlCl3
mRikn nsxhA
mRikn esa mifLFkr sp2 ladfjr dkcZu ijek.kqvksa dh
(4) vfHkfØ;k laHko gS vkSj ;kSfxd (A) eq[; mRikn
la[;k gS_______A gksxkA

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 ALLEN® Aromatic Compound 3
13. QhukWy dh fuEufyf[kr vfHkfØ;kvksa esa eq[; NH2 OH

mRikn Øe'k% A rFkk B dks ifgpkfu,% 15.

NaNO2 , HCl
"X"
"A"
273 – 278 K
OH
eq[; mRikn
(i) CHCl3, NaOH Br2 in CS2
B A
(ii) H3O + 273K mijksDr jklk;fud vfHkfØ;k esa e/;orhZ "X" rFkk
OH
OH
vfHkdeZd rFkk vfHkfØ;k 'krsZ "A" gSaA
Br
(1) rFkk +
N 2 Cl
–
NO2

(1) X- ; A- H2O/NaOH (2) X- ; A- H2O/D

CHO
OH
OH + –
N2 Cl NO2
CHO
(2) rFkk (3) X- ; A- H2 O/D (4) X- ; A- H2O/NaOH

– +
Br Cl O Na
OH OH
Br CHO 16. + NaOH
(3) rFkk

OH OH mijksDr vfHkfØ;k ds fy, fuEu esa ls dkSulh

vfHkfØ;k ifjfLFkfr;k¡ vko';d gS?

(4) rFkk
(1) 573 K, Cu, 300 atm
Br CHO
14. lwph-I dk lwph-II ds lkFk lqesy dhft,A (2) 623 K, Cu, 300 atm
lwph-I (3) 573 K, 300 atm
Cl
+
N2 Cl– (4) 623 K, 300 atm
(a) Cu 2 Cl2 + N2
¾¾¾® NO2
Cl
+ HNO3
N2 Cl–
17. H2SO4
(b) + N2
¾¾¾®
Cu ,HCl
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(c) 2CH3CH2Cl + 2Na ¾¾ ® C2H5–C2H5+2NaCl

Ether
mijksDr vfHkfØ;k esa 3.9 g csUthu dk ukbfVªdj.k
(d) 2C6H5Cl + 2Na ¾¾
® C6H5–C6H5 + 2NaCl
Ether

ij 4.92 g ukbVªkscsUthu nsrk gSA ukbVªkscsUthu dh

lwph-II
(i) oqVZ~t vfHkfØ;k (ii) lSUMek;j vfHkfØ;k izfr'kr yfC/k mijksDr vfHkfØ;k esa gS _______
(iii) fQfVax vfHkfØ;k (iv) xkVjeku vfHkfØ;k
%A (fudVre iw.kk±d esa)
uhps fn;s x;s fodYiksa esa ls lgh mÙkj dk pquko dhft,A
(1) (a) ® (iii), (b) ® (i), (c) ® (iv), (d) ® (ii) (fn;k gS % ijekf.o; æO;eku : C : 12.0 u, H : 1.0 u,
(2) (a) ® (ii), (b) ® (i), (c) ® (iv), (d) ® (iii)
(3) (a) ® (ii), (b) ® (iv), (c) ® (i), (d) ® (iii) O : 16.0 u, N : 14.0 u)
(4) (a) ® (iii), (b) ® (iv), (c) ® (i), (d) ® (ii)

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4 Aromatic Compound ALLEN®
NH2 NH2 NH2 NH2
18. mijksDr vfHkfØ;k esa (A), "X" rFkk "Y" ds NO2
HNO 3, H 2SO 4
lajpukRed lw=k Øe'k gSa : 20. 288 K
+ +
N2+ Cl —
NO2
O NO2
(1) , CH3–C–H , HCl A B C

OCH3 mijksDr nh x;h vfHkfØ;k esa izfr'kr yfC/k dk

lgh Øe gS:
(1) C > A > B (2) B > C > A
(3) A > C > B (4) C > B > A
(2)
COOH COOH

FeBr
21. + Br2 ¾¾¾¾ ® 3
+ HBr
Br
(3)
mijksDr vfHkfØ;k ij fopkj dhft, tgk¡ 7.8 g,
m-czksekscsUt+ksbd vEy izkIr djus ds fy, 6.1 g
N2+ Cl— csUtksbd vEy dk mi;ksx fd;k x;k gSA mRikn
H H
(4) , dh izfr'kr yfC/k gS_____A
, H 2O
H O H (fudVre iw.kk±d esa)
OCH3
H3C CH3 [fn;k gS : ijek.kq nzO;eku : C = 12.0u, H : 1.0u,
N
NH2 O : 16.0u, Br = 80.0 u]
19. NaNO2,HCl 22. çksVhuksa dh fuugkbfMªu ls vfHkfØ;k esa mRiUu
'X' Y ''
273K - 278 K
(eq[; mRikn) (eq[; mRikn) cSaxuh jax ds ;kSfxd dh lgh ljapuk gS :
mijksDr vfHkfØ;k ij fopkj dj crkb, X rFkk O– O–
Y gSa] Øe'k%
(1) N
+
N2Cl—
N O O
N
(1) rFkk O– O–
N CH3
CH3 (2) N
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+
N2Cl—
CH3 O O
N
(2) N N
rFkk O– O
CH3
+
Cl (3) N=N–N
N CH 3
N N
(3) rFkk CH 3 O O

Cl O O–
N (4)
N N
(4) rFkk

N O O
H3C CH3

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 ALLEN® Aromatic Compound 5
23. HNO3 rFkk H2SO4 ds feJ.k dh mifLFkfr esa 26. fuEufyf[kr;kSfxdks esa ls dkSu lk ,d
CH3MgBr ds vkf/kD; ls vfHkfØ;k] rRi'pkr
csUT+khu ds ukbVªs'ku ls ukbVªkscsUthu izkIr gksrh gS]
tyvi?kVu ij] rrh;d ,sYdksgkWy nsrk gS\
tgk¡ ij:
OCH2CH3
O CH3
(1) H2SO4 rFkk HNO3 nksuksa {kkj dk dk;Z djrs gSA (1) (2) NC
O C
(2) HNO3 vEy dk dk;Z djrk gS vkSj H2SO4 {kkj dk
CH
(3) H2SO4 rFkk HNO3 nksuksa vEy dk dk;Z djrs gSa O O

(4) HNO3 {kkj dk dk;Z djrk gS vkSj H2SO4 vEy dk (3) CH3 (4)
CH3
N OH O
NH2
CH3 +
N2 Cl –
NaNO2,HCl
A B B, Anhyd. CH2CH3
24. 273 - 278 K 273 K AlCl3
(eq[; (eq[; 27. + A + H2 O
SO3H
mRikn) mRikn) izeq[k mRikn

mijksDr vfHkfØ;k ij fopkj dhft,A blesa mijksDr jklk;fud vfHkfØ;k esa A rFkk B Øe'k% gS
(1) H3PO2 rFkk CH3CH2Cl
;kSfxd B gS:
(2) CH3CH2OH rFkk H3PO2
CH3
(3) H3PO2 rFkk CH3CH2OH
N
CH3 (4) CH3CH2Cl rFkk H3PO2
(1) HO3S N=N
28. ,d dkcZfud ;kSfxd A (C6H6O) Qsfjd DyksjkbM+
CH3 ls ,d xgjk gjk jax nsrk gSA ;g CHCl3 rFkk
(2) N=N N KOH ls vfHkfØ;k] rRi'pkr vEyhdj.k ds
CH3
mijkUr ;kSfxd B nsrk gSA ;kSfxd B dks] ;kSfxd C
CH3 dh fØ;k fifjMhfu;e DyksjksØksesV (PCC) ds lkFk
(3) HO3S N=N N
CH3 djds Hkh izkIr fd;k tk ldrk gSA A, B rFkk C
dks igpkfu,&
CH3
OH OH
(4) HO3S N
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OH CHO CH2O
CH3 (1) A = B= C=

25. ACl A
(i) (C6H5CO)2O2,HBr
P OH CH2OH OH
(ii) CoF2 OH CHO
Br (eq[; mRikn)
(2) A = B= C=
mijksDr vfHkfØ;k dk eq[; mRikn P gS% A A A
F CH2OH OH OH
OH CHO
F
(1) (2) (3) A= B= C=

Br F A A A
HO CH2OH OH
F CHO OH
(3) F (4) C=
Br Br (4) A= B=
A A A

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6 Aromatic Compound ALLEN®
29. fuEufyf[kr vfHkfØ;kvksa esa ls dkSu lh ugha gksrh gS\ 31. fuEufyf[kr vfHkfØ;kvksa dk dkSu lk ,d mRikn
NH2 NHCOCH3
lYQksu,sekbM cukus ds fy, fgUlcxZ vfHkdeZd
(1) +(CH3CO)2O/Pyridine®
ds lkFk fØ;k ugha djrk gS?
NH2 NH2
CN
(2) + H2SO4 ®

(1) + Na/Hg C2H5OH

SO3H

NH2 NH2
NO2

(3) + AlCl3 + CH3Cl ® CN

CH3
(2) + SnCl2 + HCl

NH2 NH2

(4) + HNO3/H2SO4 ® CN

Å
NO2 (3) + LiAlH4 H3O

OH OH
CHO

30. CN

Br (4) + H2/Ni
(eq[; mRikn) CH3
nh x;h vfHkfØ;k ftudh mifLFkfr esa gks ldrh
32. fuEufyf[kr ;kSfxdksa ds fy, ?kuRoksa ds ?kVus dk
gS] og bl izdkj gS:
lgh Øe gS :
(a) czksehu ty
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(b) CS2 esa Br2 , 273 K Cl Br

Cl
(c) Br2/FeBr3

(d) CHCl3 esa Br2 , 273 K Cl

(A) (B) (C) (D) Cl
uhps fn, fodYiksa esa ls lgh mÙkj pqfu, :
(1) (D) > (C) > (B) > (A)
(1) dsoy (b) rFkk (d)
(2) (C) > (D) > (A) > (B)
(2) dsoy (a) rFkk (c)
(3) (C) > (B) > (A) > (D)
(3) dsoy (b), (c) rFkk (d)
(4) (A) > (B) > (C) > (D)
(4) dsoy (a), (b) rFkk (d)

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 ALLEN® Aromatic Compound 7
Å 35. fuEufyf[kr vfHkfØ;k esa mRikn A rFkk B ds fy,
Sn + HCl "A" C6H5N 2Cl
33. C6H5NO2 Å
P
H lgh fodYi gS :
(ihys jax dk
;kSfxd) OH
Br2 (Excess) Br2
mijksDr vfHkfØ;k ij fopkj djsa] mRikn "P" gS : A B
H2O CS2, < 5°C

OH OH
N=N Br Br Br
(1) , B=
(1) A=
NH2
Br Br
N=N NH2 OH OH
(2) Br Br
(2) A= , B=

H Br Br
N OH OH
Br Br Br
(3)
, B=
(3) A=
Br
H Br
N=N–N OH OH

(4) , B=
(4) A=

Br Br
34. fuEufyf[kr :ikarj.k esa lgh vfHkdeZdksa dk lgh
36. csUthu ls 3-ukbVªkscsUtksbd vEy rS;kj djus ds
Øe gS % fy,] vfHkdeZdksa dks feykus lgh Øe gS:
NO2 OH (1) Br2/AlBr3, HNO3/H2SO4, Mg/ether, CO2, H3O+
(2) Br2/AlBr3, NaCN, H3O+, HNO3/H2SO4
(3) Br2/AlBr3, HNO3/H2SO4, NaCN, H3O+
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Cl (4) HNO3/H2SO4, Br2/AlBr3, Mg/ether, CO2, H3O+

(1) (i) Fe, HCl (ii) Cl2, HCl, 37. fuEu esa ls dkSu lk QhukWy jax ugh nsrk gS tc]
(iii) NaNO2, HCl, 0°C (iv) H2O/H+ lkUnz H2SO4 dh mifLFkfr esa mls FkSfyd
,ugkbMªkbM+ ds lkFk la?kfur djrs gS\
(2) (i) Fe, HCl (ii) NaNO2, HCl, 0°C
OH
+
(iii) H2O/H (iv) Cl2, FeCl3 OH
(1) (2)
(3) (i) Cl2, FeCl3 (ii) Fe, HCl
CH3
(iii) NaNO2, HCl, 0°C (iv) H2O/H+
OH
OH
(4) (i) Cl2, FeCl3 (ii) NaNO2, HCl, 0°C OH
+ (3) (4)
(iii) Fe, HCl (iv) H2O/H
OH

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8 Aromatic Compound ALLEN®
O 40. fuEu esa ls ,sls vfHkdeZdks dh dqy la[;k crkb;s
Br2
'A' tks ukbVªkscsathu dks ,uhyhu esa :ikUrfjr dj
38. AlBr3(C2H5)2O
(eq[; mRikn) ldrs gS______. (fudVre iw.kk±d esa)
I. Sn – HCl
nh xbZ vfHkfØ;k ij fopkj djsaA ;kSfxd A gS %
II. Sn – NH4OH
O Br III. Fe – HCl
IV. Zn – HCl
(1) V. H2 – Pd
VI. H2 – Raney Nickel
O 41. fuEufyf[kr vfHkfØ;k esa mRiUu A rFkk B dh
lajpuk;sa gSaA [Ph = – C6H5]
O
(2)
Br
+ ¾ AlCl
¾¾ ¾® A ¾ Zn
3 (2 eq )
¾ ¾® B
/ Hg
O O HCl

(3) O
O O
Br Ph Ph
A= B=
(1) OH , OH
O O
Ph Ph
(4) (2) A = ,B =
Br O OH

39. fuEufyf[kr vfHkfØ;k Øe ls fojfpr mRikn C dh O

Ph OH
(3) A =
lajpuk gS : OH , B = Ph
O
CH3COOH+SOCl2 ®A ¾¾¾® B ¾¾¾
KCN
®C
Benzene
(4) Ph Ph
AlCl3 - OH
A= , B=
NC OH O
42. vfHkfØ;kvksa ds fuEufyf[kr Øe ds fy, lgh
(1) CH3 mRikn gS %
1. Br2 /Fe/ D
¾¾¾¾¾
2. Mg/dry ether
3. CH3OH
® mRikn
O
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OCH3
CH3
(2) + HMgBr
(1)
CN
H
OCH3
H COOH + Mg
C (2)
Br
(3) CH3
CH3
OH
+ Mg
(3)
Br
CH2–CH2CN
(4) Br
H
+ Mg
(4)
OCH3

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 ALLEN® Aromatic Compound 9
43. fuEufyf[kr vfHkfØ;k Øe esa lgha A, B rFkk C dh
ifgpku dhft,A
conc.HNO 3
+
¾¾¾¾® A ¾¾¾¾¾
conc.H 2SO 4
D
Cl 2
Anhyd .AlCl 3
® B ¾¾¾
Fe/ HCl
®C

(1) A = NO2
, B =NO 2 Cl , C =Cl NH2

NO2 Cl

(2) A = NO2
, B= ,C=
Cl OH

(3) A = NO2
, B= NO2
, C= NH2

Cl Cl

NO2 NH2

(4) A = NO2
, B= , C=
Cl OH

44. fuEu vfHkfØ;k esa A dks igpkusa %

NH2

K2Cr2O7
A

O NH2

(1) (2)
KO
O

NO2 NO2
(3) (4) H
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10 Aromatic Compound ALLEN®
SOLUTION 4. Official Ans. by NTA (2)
1. Official Ans. by NTA (3) Sol. Correct sequence of reagents for the following
+
–
conversion.
NH2 N2Cl CN
NO2 Br
NaNO2 + HCl KCN
Sol. 0–5°C
Diazotization Br
Stephen SnCl2 + HCl
reduction H2O NO2 NO2 NH 2
Br2/Fe Sn
CH=O
D +HCl
Br Br
NaNO2/HCl

2. Official Ans. by NTA (3) Br

+
N 2Cl–
+ CuBr
NH 2 NH3 HBr
Br Br
conc. HNO3
Sol. (very high 5. Official Ans. by NTA (4)
+ H2SO4 –I effect)
(Anilinium ion) Sol. For nucleophile substitution in aromatic halides
Cl Cl Cl Cl
Aniline on protonation gives anilinium ion NO2 O2N NO2

which is meta directing. So considerable NO 2 NO2 NO2

(i) (ii) (iii) (iv)
amount of meta product is formed.
Correct order is :
3. Official Ans. by NTA (1) (i) < (ii) < (iii) < (iv)
More No. of NO2 substituted aromatic halide,
Sol.
increase the rate of nucleophile substitution
O OH O
C
reaction in aromatic halides.
C
O + O
6. Official Ans. by NTA (3)
C C
•O• Sol.
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OH
(i) H +
(ii) –H 2O (Pink colour) +
NºN
O NH 2 Cl–
NaNO2
C OH
+HCl
O OH
+ 1° aromatic
C+ OH OH
amine –
HO OH
EAS
EAS
O O b-naphthol
C H + C
N=N–
O –H2O O
OH
C C
HO
OH

Orange-Red. dye
OH

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 ALLEN® Aromatic Compound 11
7. Official Ans. by NTA (2) 10. Official Ans. by NTA (3)

Sol. In basic or neutral medium N–N coupling NO2

+ –
favourable while in slightly acidic medium C–N Sol. + H /HSO4
Products
coupling favourable.
NO2 NH2 N2Å Å
+
(1) Sn + HCl (2) HNO2 NO2 NO2
(A)
Diazonium
11. Official Ans. by NTA (4)
1H
NH 2 NO 2
NH2 N=N Sol.

O Br
NO2 NO2
CH3–C–Cl/AlCl3
NaBH4 NaOH O
(B) No reaction No reaction
CH3 Zn-Hg
Ph–NH2 HCl
Product
not
Br2/AlBr3
formed
NH2 N2 More active
NO2
HNO3
HNO2
(C) HÅ
Br Br
NH2 HCl
12. Official Ans. by NTA (4)

N=N NH2 NH 2 NH2 NH 2 NH2

NO2
8. Official Ans. by NTA (4) Sol. HNO3 + +
H2SO4
NO 2
1 47% 2%
2 NO2
6
Mo2O3
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Sol. + 4H2 51%

3 5 773 k,
4 10-20 atm

Mo2O3 at 773 K temperature and 10-20-atm Due to formation of anilinium ion by acid base

pressure is aromatising agent. reaction m-product is form as considerable amount.

9. Official Ans. by NTA (7)
NH2 NH 3
Sol.
O + H2SO4
C–H NH 3
HNO3
3 CHºCH Red hot Fe CO + HCl
tube AlCl3
NO2
In benzaldehyde total number of sp2 'C' are 7.

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12 Aromatic Compound ALLEN®
13. Official Ans. by NTA (2) 18. Official Ans. by NTA (1)
N2+Cl–
OH O OH
C–H + CH3–CH2–OH + CH3CHO+HCl +N 2
Sol. (B)
(1) CHCl3 + NaOH Sol.
+
(2) H3O
OCH3 OCH3
(Salicylaldehyde)
Br2 in CS 2 273 K Anisole
19. Official Ans. by NTA (2)
+
Sol. NH 2 N2 Cl
OH
NaNO2, HCl
(X) Major product
(A) 273–278 K

CH3 CH3
Br N
p–Bromo phenol
14. Official Ans. by NTA (3)
Sol. (a) ® (ii) Sand Meyer reaction CH3 CH3
N
(b) ® (iv) Gatterman reaction
(c) ® (i) Wurtz reaction
(d) ® (iii) Fittig reaction
N=N
(a) ® (ii),
(Y)
(b) ® (iv), Major product
(c) ® (i), 20. Official Ans. by NTA (4)
NH2
(d) ® (iii)
15. Official Ans. by NTA (3) HNO3 + H2SO4
Å ! Sol. 288 K
NH2 N2Cl OH
NaNO2+ HCl H2O/D Aniline
Sol. 273 – 278 K
Diazotisation NH 2 NH2 NH 2
(A) (B)
Reaction
NO 2
16. Official Ans. by NTA (2) + +
Sol. Positive zero error = 0.2 mm NO2
Main scale reading = 8.5 cm NO2
Vernier scale reading = 6 × 0.01 = 0.06 cm (A) (B) (C)
(2%) (47%) (51%)
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Final reading = 8.5 + 0.06 – 0.02 = 8.54 cm

% yield order Þ C > B > A
17. Official Ans. by NTA (80)
21. Official Ans. by NTA (78)
NO2
6.1
Sol. Moles of Benzoic acid =
HNO3 122
Sol.
H2SO4 = moles of m-bromobenzoic acid
1 mole 1 mole So, weight of m-bromobenzoic acid
6.1
78gm 123gm = ´ 201gm
122
123 = 10.05 gm
3.9gm × 3.9 = 6.15gm
78 Actual weight
% yield = ´ 100
But actual amount of nitrobenzene formed is Theoretical weight
4.92 gm and hence. 7.8
= ´ 100
4.92 10.05
Percentage yield = ´ 100 = 80%
6.15 = 77.61%

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 ALLEN® Aromatic Compound 13
22. Official Ans. by NTA (4) 26. Official Ans. by NTA (1)
O Sol.
R O
OH OH
Sol. +NH2–CH–C–OH O CH CH3MgBr OH
(excess)
OH H3 O+
+ CH3–C–CH3
OH! O
O CH3
O! O Tertiary alcohol

OCH2CH3
N + RCHO CH3MgBr OCH2CH3
H3C
+CO2 NC (excess)
H3O + C
+4H2O C C
O O
O
CH CH
Ninhydrin Test
23. Official Ans. by NTA (4)
Sol. Reagent for nitration of Benzene O OH
Å CH3MgBr CH3
H 2SO 4 + HNO 3 € HSO 41 + H 2 N O 3 CH3 (excess)
(Acid ) (Base) H3 O+ CH3
Å Å
H 2 N O3 € H 2O + N O 2 OH
Phenolic –OH group and tertiary
NO2 alcohol is present thus two
functional groups are present in
Å the product
+ NO2 ¾®
O OH CH3
HO
Nitrobenzene CH3MgBr
(excess)
24. Official Ans. by NTA (3) +
H3 O+
+
NH2 N2 O HO CH3
OH
Two 3° alcohol
NaNO2 + HCl
A(major product) Since the given question is single correct choice
0–5°C
the best appropriate option is (A)
SO3H SO3H
27. Official Ans. by NTA (1)
+ Sol.
N2 NMe2 NMe2 [A] H [B]
H3PO2 Et-Cl
+ Reduction AlCl3
–N2 ­
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SO3H N=N SO3H

28. Official Ans. by NTA (1)
B(major product)
O
25. Official Ans. by NTA (4) Sol.
FeCl3
C6H6O = Dark
(C6H5CO)2 O2, HBr
[A] green
Sol.
Br AMKR Reimer–tiemann reaction CHCl3 + KOH
Product
O
O OH
Br C–
CH2–OH PC
Br ¯ CoF2 (Swart reaction) Oxidation

F [C] [B]

Br

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14 Aromatic Compound ALLEN®
29. Official Ans. by NTA (3) 34. Official Ans. by NTA (3)

+ –
NH2 NH2–AlCl3 Sol.
Sol. + AlCl3
Lewis Lewis Deactivated
base base Ring
Friedel craft Me–Cl
AlCl3
Alkylation
not occurs

(1) Aniline is lewis base give acid base reaction

with AlCl3 and form Anilinium ion
(2) Anilinium ion has strongest deactivated ring
so further Friedel craft Alkylation not
occurs.
30. Official Ans. by NTA (3) 35. Official Ans. by NTA (2)

Sol. Bromine water gives tribromo products, other OH OH

OH
Br Br
gives monobromo products in which para is Sol. Br2 Br2
A B
H2O CS2,<5°C
major product.
Br Br
Imino Group
CN CH=NH
36. Official Ans. by NTA (4)
SnCl2 + HCl
31.
Sol.
Imino group does not react
with Hinsberg reagent NO2 NO2

HNO3 Br2
32. The density order + H2SO4 + AlBr3
Br
Br Cl Cl
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Mg(Ether)
(D) > (C) > (B) > NO2 NO2
Cl Cl
CO2
33. Official Ans. by NTA (2) H+
CO2H MgBr
Sol. 3–nitrobenzoic acid

NO2
NH2
NH2 + 37. Official Ans. by NTA (2)
Sn + HCl Ph–N2Cl–

Sol. Only p-methyl, phenol does not give any colour

N=N
(P)
Yellow colored
with phthalic anhydroxide with cons. H2SO4.
azo dye

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 ALLEN® Aromatic Compound 15
38. Official Ans. by NTA (3) 42. Official Ans. by NTA (2)
O Br
CH2–CH2–CH2–CH3
Sol. Br2 + Fe Mg
PhMgB
(m–directing) D Dry Ether
CH3OH
Br2+AlBr3(El2O)
Br
O + M
OCH3

43. Official Ans. by NTA (1)

Br Sol.
39. Official Ans. by NTA (1)
NO2
C–CH3
Sol. CH3–C–OH+SOCl2®CH3–C–Cl
O HNO3 + H2SO4 Cl2
O O
(B) D An. AlCl3
(A)
CH3 [A]
C–CN
B + KCN
+OH– OH NH2 NO2
NO2 NH2
Fe/HCl
40. Reagents used can be
Cl Cl
(i) Sn + HCl [C] [B]
(ii) Fe + HCl
44. Official Ans. by NTA (1)
(iii) Zn + HCl
(iv) H2 – Pd NH2 O
(v) H2 (Raney Ni) Sol. K2Cr2O7
41. Official Ans. by NTA (1) [O]

Sol. O Aniline O
O – AlCl31 [A]
AlCl3
O O
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O O

[E.A.S.]

O
C–CH2–CH2–COOH
(A)

Zn – Hg HCl

Ph – CH2 – CH2 – CH2 – COOH

(B)