CHEMISTRY Revision DPP 4 Solution

ORGANIC CHEMISTRY
TARGET : JEE(MAIN)
 

E E ST INFORM ATIO
DPP
DAILY PRACTICE PROBLEMS
CLASS - XII NO. 4
Hints & Solutions
(i) DCI (1 equiv.) (ii) DI

3. CH3CCH CH3C(CI)=CHD CH3C(I)(CI)CHD2
5.
COOH
6. 
NaOH / CaO


7. (1) 2R  X  2Na  R  R  2NaX

dryether
(2) CH3 – C – CH3 NH 2NH2 / KOH CH3 – CH2 – CH3

Alkane
O
Carbonyl compound
Lindlar's R R
(3) R–CC–R C=C
Catalyst H H
cis
'kq"d bZFkj
Sol. (1) 2R  X  2Na   R  R  2NaX
NH2NH2 / KOH
(2) CH3 – C – CH3 CH3 – CH2 – CH3
,Ydsu
O
dkcksZfuy ;kSfxd
fy.Mykj R R
(3) R–CC–R C=C
mRizsjd H H
lei{k
Br CN
| |
10. C2H5Br 
Alc.KOH
 CH2=CH2 
Br2
 CH2 – CH2 KCN H3O
 CH2 – CH2   CH2 – CH2 – COOH
CCl4 (excess)
| | |
Br CN COOH
C2H5OH
PCl
12. 5
C2H 5Cl POCl3  HCl
C2H5Cl + AgNO2 C2H5NO2 + AgCl
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PAGE-1
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1. PBr E2reaction
20. OH 
3
 Br 
SN 2reaction 2. KOH(alc.)
O O
O
Wolf CH2
25. C=O
Kishner
oqYQ
C=O CH2
fd'uj
26. Correct order of SN 2Ar reaction is:

SN 2Ar vfHkfØ;k dk lgh Øe gS&
F Cl Br I
> > >
NO2 NO2 NO2 NO2
OCH3 O–CH3 
O—CH3
OCH3
H—Br Br HBr H
39.   Br

CH=CH2 CH–CH3 CH–CH3
CH–CH3
Br
Br
OH
+ CH3–Br
Br–CH–CH3
41. Neutral FeCl3  –ve  phenol is absent.

Fehling solution  –ve –CHO is absent.
Iodoform reaction  +ve –COCH3 or –CH(OH)–CH3 is present.
Grignard reagent +ve Electrophilic center or acidic H is present.
OH
CH–CH3 obeys all above statements.
OCH3
Sol. mnklhu FeCl3  –ve  fQukWy vuqifLFkr gSA
Qsgfyax foy;u  –ve –CHO vuqifLFkr gSA
vk;MksQkWeZ vfHkfØ;k  +ve –COCH3 ;k –CH(OH)–CH3 mifLFkr gSA
fxzxukMZ vfHkdeZd +ve bysDVªkWuLusgh dsUnz ;k vEyh; H mifLFkr gSA
OH
CH–CH3 mi;qZDr lHkh dFkuks dk ikyu djrk gSA
OCH3
43. Ph–CC–Ph 
X
 
Br2

Na(NH3 ( )) CCl4
PAGE-2
O OH
LiAlH
48. KMnO

4
 
4


H , COOH ether CH2OH
O O
O
NaBH4 CH–CH2–Br CH—CH2
C
53. CH2–Br 
MeOH
55. t-butyl methyl ehter is a mixed ether and for the preparation of mixed ethers in high yield the essential
condition is the use of primary alkyl halide.
Thus, 
NaBr

This reaction is williamson's synthesis.

Sol. t-C;wfVy esfFky bZFkj ,d fefJr bZFkj gS vkSj blds fuekZ.k esa 1° ,fYdy gSykbM mi;ksx fd;k tkrk gSA

NaBr

;g vfHkfØ;k fofy;elu la'ys"k.k dgykrh gSA
56. Greater is the electron density on aromatic ring, greater will be the reactivity towards electrophilic
aromatic substitution.
,jksefS Vd oy; ij ftruk vf/kd bysDVªkWu ?kuRo gksxk bysDVªkWuLusgh ,jkseSfVd izzfrLFkkiu fØ;k'khyrk mruh gh
vf/kd gksxhA
57. The SN1 reactivity is proportional to stability of carbocations formed in the rate determining step.
SN1 vfHkfØ;k dh fØ;k'khyrk nj fu/kkZjd in esa cuus okys dkcZ/kuk;u ds LFkkf;Ro ds lekuqikrh gksrk gSA
OH
OH
H2SO4 (Cat.)
OH 
58.  O
CHCl3
COOEt O
It is acid catalysed intramolecular trans esterification reaction.
;g vEy mRizsfjr vUr%v.kqd Vªkal ,LVjhdj.k vfHkfØ;k gSA
O
(1) t-BuOK
59.
E2 elimination
reaction
O
(2) Conc. H2SO4/
Electrophilic
subsitution
PAGE-3
–O–H
compounds –N–H
61. PhMgBr + having acidic
hydrogen –S–H
–CC–H
–O–H
vEyh; gkbMªkstu –N–H
PhMgBr +
Sol. j[kus okys ;kSfxd
–S–H
–C  C–H
O
B +M
62. O , C—O— ,
A –M
A B
A>B B>A
O O +M
–M –M
O
+M
C—N— , ,
A B
H
B>A B>A
O
+M
MeO— O H—C— OH
, –M
+M +M
A B A B
A>B B>A
63. CH3—O— —O— —O— —O—CH3

H H
(1) (2)
Benzene oxygen bond has partial double bond character.
csUthu vkWDlhtu ca/k] vkaf'kd f}ca/k xq.k j[krk gSA
O Br ,
64. , , Cl , ,
Cl  O Cl
Give good yield of SN2 reaction.
SN2 vfHkfØ;k dh Js"B yfC/k nsrs gSaA
CHO
CH–CH3
65. (x) =
CHO CH3
CH–CH3 CH–CH3 OH
O
Zn–Hg
   
(i ) O2
CH3–C–CH3 +
HCl (i i) H3O
(z)
(x) (y) (w)
PAGE-4
OH OH
Br Br
+ 3Br2 (aq)  + 3HBr
Br
67.   
Cl 2 / hv
+ +
Product = 5.
O OH
CN C
OH OH
H / H2O
68. (i) 

O
O 
(ii) 
H

 /
H2O
O NH2 O OH
C C
OH OH
H / H2O
(iii) 

O O O
|| || ·· ||
(—C  N, —C—NH2 , —C—N ; all groups give —C—OH on acid hydrolysis)
O O O
|| || ·· ||
(—C  N, —C—NH2 , —C—N ; vEy ty vi?kVu ij lHkh lewg —C—OH nsrs gS)

NC NH3
OH OH
H / H2O
(iv) 
 + HCOOH
OH H
OH O O HO
H
+
(v) O O 

H2O O OH
O OH OH
OH
+ HCHO
O CH3
OH
(vi) does not undergo any hydrolysis dksbZ Hkh ty vi?kVu ugh nsrk gSA
OH O OH O
OH
(vii) O 
H2O
OH
O O
PAGE-5
O O OH
O O OH
OH
O O OH
(viii) 
 H  + HCHO
H2O
69. Gemdicarboxylic acid and -keto acid can shows decarboxylation on heating.

NMe3
–
70. 
OH
(3-H)

(major) ¼eq[;½
H
H
71. OH H
H +
OH H-shift O
OH 
(–H2O)
H
CH=O CH2–OH CH2
LiAlH4 H+

(–H2O)
(A) (B)
H
CH3 –H
+ CH3
(C)
molecular mass of product (c) = 96 (W)
N = 96 ÷ 12 = 8
72.
 
(i) C H3  C H3  CH 3  CH 3


(ii) CH3  C H2  CH3  CH2  CH3  CH2  CH2  CH3
(iii) CH3  CH3  CH2 CH3  CH2  CH3
PAGE-6
(iv)
O O
CH3—C—ONa+ CH3— CH2—C—ONa

Sol.
lksfM;e ,FksukW,V lksfM;e izksisukW,V
dkWYcs oS|qrvi?kVu
O O
CH3—C—ONa+ CH3— CH2—C—O
,uksM ij 2e
 
(i) C H3  C H3  CH 3  CH 3


(ii) CH3  C H2  CH3  CH2  CH3  CH2  CH2  CH3
(iii) CH3  CH3  CH2 CH3  CH2  CH3
(iv) CH2–CH2–CH3–CH2 CH2=CH2+CH3–CH3
fo"kekuqikrhdj.k vfHkfØ;k
H
  
73. CH3  C  C N a   CH3 – C  C – D 
D 3O D2
 CH3 – CD = CD2
74. Compound X = , Compound Y =

HO
Therefore molecular weight difference equal to 16 gram/mol.
Sol. ;kSfxd X = , ;kSfxd Y =

HO
blfy, v.kqHkkj varj 16 xzke@eksy ds cjkcj gksrk gSA
75. (i), (ii), (iii), (iv), (v), (vi)
PAGE-7

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ORGANIC CHEMISTRY

CLASS - XII NO. 4

Hints & Solutions

(i) DCI (1 equiv.) (ii) DI

7. (1) 2R  X  2Na  R  R  2NaX

(2) CH3 – C – CH3 NH 2NH2 / KOH CH3 – CH2 – CH3

26. Correct order of SN 2Ar reaction is:

> > >

NO2 NO2 NO2 NO2

41. Neutral FeCl3  –ve  phenol is absent.

CH–CH3 obeys all above statements.

CH–CH3 mi;qZDr lHkh dFkuks dk ikyu djrk gSA

This reaction is williamson's synthesis.

;g vfHkfØ;k fofy;elu la'ys"k.k dgykrh gSA

63. CH3—O— —O— —O— —O—CH3

CH3—C—ONa+ CH3— CH2—C—ONa

CH3—C—ONa+ CH3— CH2—C—O

74. Compound X = , Compound Y =

Sol. ;kSfxd X = , ;kSfxd Y =

75. (i), (ii), (iii), (iv), (v), (vi)

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