CHEMISTRY Revision DPP 2 Solution

ORGANIC CHEMISTRY
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E E ST INFORM ATIO
DPP
DAILY PRACTICE PROBLEMS
Class - XII NO. 2
Hints & Solutions

3. Secondary amine does not give +ve test with CHCl3 / KOH.
Sol. f}rh;d ,ehu CHCl3 / KOH ds lkFk /kukRed ijh{k.k ugha nsrk gSA
O Zn, H O
5. CH3CH=CHCH3 
3
 
2


Re ductive ozonolysis
O Zn, H O
Sol. CH3CH=CHCH3 
3
 
2


vip;ukRed vkstksuhvi?kVu
9. C5H10O Degree of unsaturation vlar`Irrk dh dksfV = 1

O
O
(i) (ii) CH3–CH–CH2–C–H
CH3–CH2–CH2–CH2–CH
CH3
O CH3 O
(iii) (iv)
CH3 CH3
O
O
(v)
(vi)
CH3
O
(vii)
Total no. of carbonyl compounds are seven.
dqy dkcksZfuy ;kSfxdks dh la[;k lkr gksxhA
CH3 CH2–OH
10. and are functional isomers.
o-Cresol Benzyl alcohol

CH3 CH2 –OH
Sol.
rFkk fØ;kRed leko;oh gSA
o-fØlkWy csf Uty ,YdksgkWy
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12.
n = 3 with unsymmetrical ends.
no. of G.I. = 2n = 23 = 8
Sol.
n = 3 with unsymmetrical ends.
no. of G.I. = 2n = 23 = 8
vlefer dsUnzks dh la[;k n = 3
G.I. dh la[;k = 2n = 23 = 8
HOOC COOH HOOC H

13. C=C
H H H COOH
Maleic acid Fumaric acid
Fumaric acid and maleic acid are geometrical isomers.
HOOC COOH HOOC H
Sol. C=C
H H H COOH
eSysb d vEy ¶;wesf jd vEy
¶;wesfjd vEy rFkk eSysbd vEy T;kfefr; leko;oh gSA
14. * * * * Sign represent asymmetric carbon.
OH OH OH
3-Chiral carbon with unsymmetrical ends so, no. of optically active isomers = 2 3 = 8
Sol. * * * * fpag vlefer dkcZu dks fu:fir djrk gSA
OH OH OH
vlfer fljs okys ;kSfxdks esa 3 fdjsy dkcZu gSA vr% izdkf'kd lfØ; leko;oh;ksa dh la[;k = 23 = 8
CH3 COOH
15. (1) HO H H OH HO H
CH3 COOH CH3
identical
OH H
(2) CH3 OH H COOH HO CH3
COOH CH3 COOH
Enantiomers
OH COOH
(3) H CH3 CH3 H H CH3

OH COOH OH
identical
OH CH3
(4) HOOC OH HOOC H HOOC OH
H CH3 H
identical
COOH CH3 COOH
Sol. (1) HO H H OH HO H
CH3 COOH CH3
le:ih
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H OH H
(2) CH3 OH H COOH HO CH3
COOH CH3 COOH
izf rfcEc:ih leko;oh gS
COOH OH COOH
(3) H CH3 CH3 H H CH3
OH COOH OH
le:ih
CH3 OH CH3
(4) HOOC OH HOOC H HOOC OH
H CH3 H
le:ih
16.
(2R, 3S)–3–Bromo–2–butanol
(2R, 3S)–3–czkseks–2–C;wVsukWy
17.
foofje:ih
izfrfcEc:ih foofje:ih
18. Chlorination
(Dyksjhuhdj.k)
PAGE-3
Total 4-isomers
dqy 4-leko;oh
19. Acetyl acetone is liquid and exist mainly as III due to intramolecular H-bonding and the correct answer
is III > II > I.
Sol. ,lhfVy ,lhVksu nzo gS rFkk ;g vUr% v.kqd H-ca/ku ds dkj.k eq[;r% III esa ik;k tkrk gS rFkk lgh mÙkj III > II > I
gSA
27. Phenols are more acidic than alcohols, due to the stabilisation of phenoxide ion by resonance.
Phenoxide ion is stablized due to following resonating structures :
Sol. fQ+ukWy] ,YdksgkWy dh rqyuk esa vf/kd vEyh; gksrk gS D;ksafd fQ+ukWDlkbM vk;u vuqukn }kjk LFkkf;Ro izkIr gksrs gSaA
fQ+ukWDlkbM vk;u fuEu vuquknh lajpukvksa ds dkj.k LFkkf;Ro izkIr djrs gSaA
OH 
H
28. (I)   ; No any stabilising factor

H
(II)   ; –ve charge stabilised by two equivalent resonating structures.

H
(III)   ; –ve charge stabilised by three NO2 groups (–m, –
effects)
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
H
(IV)   ;–ve charge stabilised by resonance only.
OH 
H
Sol. (I)   ; LFkkf;Ro dk dksbZ dkjd ugha gSA

H
(II)   ; _.kkos'k dk LFkk;hdj.k nks leku ÅtkZ dh vuquknh lajpukvksa }kjk gksrk gSA

H
(III)   ; _.kkos'k dk LFkk;hdj.k rhu NO2 lewg ds (–m, – izHkko)
}kjk gksrk gSA

H
(IV)   ; _.kkos'k dsoy vuqukn }kjk LFkk;h gSA
vr% Ka dk Øe III > II > IV > I gSA
5 3 1
4 2
6
29. (4-Bromomethyl-2-chlorohexane) (4-czkseksesfFky -2-DyksjksgsDlsu)
Br Cl
CH3
30. CH3–C–CH2–Br is named as neopentyl bromide in common naming. (dk lkekU; uke fu;ksisfUVy czksekbM
CH3
gS)
O O O O
31. , , , , O , O =6
32.
Total resonating structures = 5

dqy vuquknh lajpuk,¡ = 5
33. Ester group when attached by C=O then it shows –M effect.

tc ,LVj lewg C=O ls tqM+rk gS] rks ;g –M izHkko n'kkZrk gSA

N 
35. 2– & are Aromatic ,jkseSfVd gSaA
N
 
36. C Triphenyl methyl carbanion is most stable among them due to resonance.
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Sol. C VªkbZQsfuy esfFky dkcZ_.kk;u dk LFkkf;Ro vuqukn ds dkj.k mijksDr lHkh esa lcls vf/kd gSA
37. Electron releasing groups (+M, +I) increase the electron density while electron withdrawing
group(-M,-I) decrease the electron density of the benzene ring.
Sol. csUthu oy; esa bysDVªkWu nkrk lewg (+M, +I) bysDVªkWu ?kuRo c<+krs gSa tcfd bysDVªkWu vkd"khZ lewg (-M,-I)
bysDVªkWu ?kuRo ?kVkrs gSaA
39. (1) Ph–CH–CH3  in carbanion hyperconjugation is not observed.

(1) Ph–CH–CH3  dkcZ_.kk;u esa vfrla;qXeu ugha gksrk gSA
(2)  5--Hydrogen (gkbMªkstu)
42. Ring along with the  bond has single group then no other configuration is possible in six memebered
ring.
 cU/k ds vuqfn'k oy; tc ,d lewg j[krh gS rc N% lnL; oy; esa vU; foU;kl lEHko ugha gksrs gSaA
43. 'N' is sp2 and lone pair is delocalized.

'N' sp2 ladfjr gS rFkk foLFkkuhÑr ,dkdh ;qXe mifLFkr gSA
44. Same alkyl groups are present in ketone of option (4) so gives only one oxime.
fodYi (4) ds dhVksu esa leku ,fYdy lewg mifLFkr gSa] blfy, dsoy ,d vkWDlhe nsrs gSA
46. Electron withdrawing groups increases the enol content.

bysDVªkWu vkd"khZ lewg bZukWy ?kVd dks c<+rk gSA

48. Ph  NH3Cl + NH3  Ph–NH2+NH4Cl
NH3 is more basic than Ph–NH2, so reaction proceeds in forward direction.
NH3, Ph–NH2 dh rqyuk esa vf/kd {kkjh; gS] blfy, vfHkfØ;k vxz fn'kk esa gksxhA
49. has a chiral atom, so it is chiral and other compounds are symmetrical & achiral.
H Br
;g ,d fdjSy ijek.kq j[krk gS blfy, fdjSy gS rFkk vU; lHkh ;kSfxd lefer rFkk vfdjSy gSA
H Br
50. CH3–C * C–CH2–CH2–CH3

H C2H5
3-Ethyl hex-2-ene can show geometrical isomerism across the double bond.
3-,fFky gsDl-2-bZu f)cU/k ds }kjk T;kfefr; leko;ork n'kkZ ldrk gSA
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51. Ph – CH = CH – CH = CH – Ph
(i) Cis – Cis (lei{k&lei{k)
(ii) Trans – Trans (foi{k&foi{k)
(iii) Cis – Trans (lei{k&foi{k)
COOH COONa
NaHCO3 + CO2
54.
O–C–CH3 O–C–CH3
O O
Aspirin is stronger acid than H2CO3, so it gives CO2 gas with NaHCO3. Rest of all are weaker acids.
,Lizhu] H2CO3 dh rqyuk esa izcy vEy gS blfy, ;g NaHCO3 ds lkFk xSl nsrk gSA vU; lHkh nqcZy vEy gSA
55. In cycloalkene cis-isomer is more stable than trans isomer till 12 member ring.
lkbDyks,Ydhu esa 12 lnL; oy; rd lei{k leko;oh] foi{k leko;oh dh rqyuk esa vf/kd LFkk;h gksrk gSA
O
56. CH2=CH–CH=CH–CH3 
3  CH =O + CH –CH=O + OHC–CHO
2 3
Zn, H2O
57. Benzaldehyde can not give Fehling test and Iodoform test but Acetaldehyde gives.
csUtsfYMgkbM Qsgfyax ijh{k.k rFkk vk;ksMksQkWeZ ijh{k.k ugha ns ldrk gS ysfdu ,lhVsfYMgkbM nsrk gSA

58.  NH3 group cannot exert M effect as it cannot accept e- pair due to unavailability of vacant p/d orbitals.

gy%  NH3 lewg M izHkko ugha n'kkZ ldrk D;ksafd ;g fjDr p/d d{kdksa dh vuqifLFkfr ds dkj.k e- ;qXe xzg.k ugha dj
ldrkA
59. Due to ortho effect.

vkFkksZ izHkko ds dkj.k
61.
62.
63. Those N which have more e– density than N of aniline are more basic.
I, II, III, IV, VIII are more basic than aniline.
og N tks ,fuyhu ds N dh rqyuk esa vf/kd e– ?kuRo j[krk gS] vf/kd {kkjh; gksrk gSA
Me Me Me Me
H H H H
64.
H H H H
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65. Acetal and sucrose do not give any precipitation with tollen's reagent.
Sol. ,slhVsy o lqØksl VkWysu vfHkdeZd ds lkFk dksbZ vo{ksi ugha nsrk gSA
*
66. *
*
*
67. 5 (b,c,d,e,h)
68. This is the case of compound having similar ends

 chiral isomers = 2n–1 = 24–1 = 23 = 8
Enantiomeric pairs = 4
Sol. ;g leku vUr j[kus okys ;kSfxd dh fLFkfr gksrh gSA
 fdjSy leko;oh = 2n–1 = 24–1 = 23 = 8
izfrfcEc:ih ;qXe = 4
CH
 CH

2 2
69.
OMe
+m group (+H effect)
 
Benzylic (2º) (Extend and resonance)

CH
 CH

2 2
Sol.
OMe
+m lewg (+H izHkko)
 
csfUtfyd (2º) (izlkj rFkk vuqukn)
H C
70. CCCCC CCCCC CCCC

OH OH OH
(d  ) (d  )


71. , , , ,
  
2
PAGE-8
H H CH3
72. C —C , C —CHO
O O O
O O O
|| ||
NO2 SO3H C–OH
73.
O
|| ||
O O
74. , , , are aromatic species. ,sjkseSfVd Lih'kht gSaA
75. Following acids are stronger than H2CO3 so these will liberate CO2 with NaHCO3.
fuEu vEyksa dh vEyh;rk H2CO3 ls vf/kd gS blfy, ;s NaHCO3 ds lkFk CO2 xSl eqDr djrs gSA
CCl3COOH
PAGE-9

CHEMISTRY Revision DPP 2 Solution

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ORGANIC CHEMISTRY

Class - XII NO. 2

Hints & Solutions

9. C5H10O Degree of unsaturation vlar`Irrk dh dksfV = 1

10. and are functional isomers.

o-Cresol Benzyl alcohol

o-fØlkWy csf Uty ,YdksgkWy

HOOC COOH HOOC H

14. * * * * Sign represent asymmetric carbon.

(3) H CH3 CH3 H H CH3

Phenoxide ion is stablized due to following resonating structures :

}kjk gksrk gSA

Total resonating structures = 5

33. Ester group when attached by C=O then it shows –M effect.

39. (1) Ph–CH–CH3  in carbanion hyperconjugation is not observed.

(2)  5--Hydrogen (gkbMªkstu)

(3)  9--Hydrogen (gkbMªkstu)

(4)  5--Hydrogen (gkbMªkstu)

43. 'N' is sp2 and lone pair is delocalized.

46. Electron withdrawing groups increases the enol content.

50. CH3–C * C–CH2–CH2–CH3

59. Due to ortho effect.

68. This is the case of compound having similar ends

Benzylic (2º) (Extend and resonance)

csfUtfyd (2º) (izlkj rFkk vuqukn)

70. CCCCC CCCCC CCCC

74. , , , are aromatic species. ,sjkseSfVd Lih'kht gSaA

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