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ORGANIC CHEMISTRY

TARGET : JEE (Main + Advanced) 2016


Course : VIJETA (JP) Date : 18-05-2015 NO. 10 & 11

TEST IN FORMATI ON
DATE : 07.06.2015 CUMULATIVE TEST (CT) - 1 (ADVANCED)

Syllabus : Stereoisomerism & Organic reaction mechanisms-I & II, Cheminfo (Till date)

This DPP is to be discussed in the week (18-05-2015 to 23-05-2015)


DPP No. # 10 (JEE-ADVANCED)
Total Marks : 58 Max. Time : 36 min.
Multiple choice objective ('–1' negative marking) Q.1 to Q.5 (4 marks, 2 min.) [20, 10]
Comprehension ('–1' negative marking) Q.6 (i to iii) (3 marks, 2 min.) [09, 06]
Matching List Type (Only One options correct) ('–1' negative marking) Q.7 (3 marks, 2 min.) [03, 02]
Match the Following (no negative marking) Q.8 (8 marks, 6 min.) [08, 06]
Integer Type Questions Q.9 to Q.10 (3 marks, 2 min.) [06, 04]
ChemINFO : 4 Questions ('–1' negative marking) Q.11 to Q.14 (3 marks, 2 min.) [12, 08]

1. Select the correct statement about Grignard reagent.


(A*) In Grignard reagent 3 and 4 membered cyclic ethers can not be used as a solvent.
(B) In case of Grignard reagent any alkyl, aryl, vinyl, allyl group can not be taken as organic part.
(C*) Grignard reagent can not be prepared from alkyl or aryl fluorides.
(D*) The role of ether is to solvolyse RMgX and also provide medium for reaction.
fxzU;kj vfHkdeZd ds ckjs esa lgh dFku pqfu;sA
(A*) fxzU;kj vfHkdeZd esa foyk;d ds :i esa 3 vkSj 4 lnL; ;qDr pfØ; bZFkj dk mi;ksx ugha dj ldrsA
(B) fxzU;kj vfHkdeZd esa dksbZ Hkh ,fYdy] ,fjy] foukby] ,fyy lewg dks dkcZfud Hkkx esa mi;ksx ugha dj ldrs gSA
(C*) ,fYdy vFkok ,fjy ¶yksjkbM ls xzhU;kj vfHkdeZd ugha cuk ldrs gSA
(D*) bZFkj dk dk;Z RMgX dks foyk;dhdj.k vkSj vfHkfØ;k ds fy, ek/;e iznku djuk gksrk gSA
2.* Select the reaction in which one organometallic compound produces another organometallic compound.

Ether
(A*) CH3MgBr + HC  C – Ph  (B*) Ether
+ CH3MgBr 
 

(C) + Ether (D) CH3CH2Na + Ether



  


Ether
Sol. (A) CH3MgBr + H – C  C – Ph 
 CH4 + Ph – C  C – MgBr (organometallic compound)

(B) + CH3MgBr  + CH4

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(C) +  +

(D) +  CH3 – CH3 +

ml vfHkfØ;k dk p;u dhft;s ftlesa ,d dkcZ/kkfRod ;kSfxd nqljk dkcZ/kfRod ;kSfxd mRiUu djrk gSA

(A*) CH3MgBr + HC  C – Ph  (B*) + CH3MgBr 

(C) +  (D) CH3CH2Na + 

Sol. (A) CH3MgBr + H – C  C – Ph  CH4 + Ph – C  C – MgBr (dkcZ/kkfRod ;kSfxd)

(B) + CH3MgBr  + CH4

(C) +  +

(D) +  CH3 – CH3 +

3.* The correct statements about following reaction are :


H
 ester + water


(A*) It is an equilibrium reaction (B*) O18 is found in ester

(C*) One of the intermediate is (D) ionises to Et in this reaction

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fuEu vfHkfØ;k ds fy, lR; dFku gS %
H

 ,LVj + ty

(A*) ;g lkE;koLFkk vfHkfØ;k gSA (B*) O18, ,LVj esa izkIr gksrk gSA

(C*) ,d e/;orhZ gSA (D) bl vfHkfØ;k esa vk;fud`r gksdj Et vk;u cukrk gSA

Sol. It is fisher esterification reaction. (;g fQ'kj ,LVjhdj.k vfHkfØ;k gS)

+ H 2O

4.* Which of the followings are correct :


fuEUk esa ls dkSu&dkSu lgh gSa %
(A*) CH3COCl > (CH3CO)2O > CH3COOEt > CH3CONH2 (Rate of hydrolysis) (ty vi?kVu dh nj)

(B*) CH3–CH2–COOH > > (Rate of esterification) (,LVjhdj.k dh nj)

(C) > > (Rate of esterification) (,LVjhdj.k dh nj)

(D*) > > (Rate of esterification)

(,LVjhdj.k dh nj)
Sol. (A) Rate of hydrolysis in SN2 tetrahedral is  leaving group ability
1
(B) Rate of esterification  Branching at  carbon of acid
(C) Rate of estrification  nucleophilicity of alcohol.
(D) Electron withdrowing group increases rate of esterification.

(A) SN2 prq"Qydh; esa tyh;dj.k dh nj  fu"dklu {kerk


1
(B) ,LVjhdj.k dh nj  
(C) ,LVjhdj.k dh nj  ,YdksgkWy dh ukfHkdLusfgrk
(D) bysDVªkWuvkd"khZ lewg ,LVjhdj.k dh nj dks c<+krk gSA

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5.* Which of the following is/are nucleophilic addition reaction/s ?
fuEu esa ls dkSulh vfHkfØ;k ukfHkdLusgh ;ksxkRed vfHkfØ;k,sa gSa \

(A*) (B) CH3–COOH + CH3–CH2–OH

(i)
(C*) CH3 MgBr + HCHO   CH CH OH
(ii) H O 3
2 2

(D) Ph–CH2–COOH + SOCl2 

Sol. LiAlH4 provides nucleophilie in reaction A. vfHkfØ;k A esa LiAlH4 ukfHkdLusgh iznku djrk gSA
acts as nucleophile in reaction C. vfHkfØ;k C esa ,d ukfHkdLusgh dh rjg dk;Z djrk gSA

6. Comprehension vuqP Ns n
Observe the esterfication mechanisms for primary and tertiary alcohols.
izkFkfed ,oa r`rh;d ,YdksgkWy ds fy, ,LVjhdj.k dh fØ;kfofèk izsf{kr dhft,&

Type.1 CH3–COOH + Conc. H2SO 4


   

Mechanism fØ;kfofèk

H 
 Step 3
Step 1.
 


–H
–H2O

Type. 2 + Conc. H2SO 4


   

H 
Mechanism fØ;kfofèk 
Step 1.

(i). CH3–COOH + Conc. H2SO 4


    (P)
Conc. H SO
CH3–COOH +   2  4
 (Q)
In the above reaction (P) and (Q) are respectively :
mijksDr vfHkfØ;k ds fy, Øe'k% P rFkk Q gS&

(A) , (B*) ,

(C) , (D) ,

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(ii). CH3COOH + Conc. H2SO 4
    (X)

CH3–COOH + Conc. H2SO 4


    (Y)

(A*) (X) is optically active while (Y) is optically inactive


(B) Both (X) and (Y) are optically active
(C) Both (X) and (Y) are optically inactive
(D) (X) is optically inactive while (Y) is optically active.
(A*) (X) izdkf'kd lfØ; gS] tcfd (Y) izdkf'kd vfØ; gSA
(B) nksuksa (X) rFkk (Y) izdkf'kd lfØ; gSA
(C) nksuksa (X) rFkk (Y) izdkf'kd lfØ; gSA
(D) (X) izdkf'kd vfØ; gS] tcfd (Y) izdkf'kd lfØ; gSA

(iii). (+) Octan-2-ol esterifies with Acetic acid to give optically inactive racemised product. It must have gone by
(A) Type I mechanism (B*) Type II mechanism
(C) Mix type I and type II mechanism (D) More by type I and less by type II mechanism
tc (+) vkWDVsu-2-vkWy dks ,flfVd vEy ds lkFk ,LVªhd`r djrs gS rks mRikn izdkf'kd vfØ; jslsfed feJ.k izkIr gksrk
gS rks crkb;s ;g fdlds }kjk lEiUu gksuk pkfg,A
(A) fØ;kfofèk-I-}kjk (B*) fØ;kfofèk-II- }kjk
(C) fØ;kfofèk-I-rFkk fØ;kfofèk-II-ds fefJr izdkj }kjk (D) fØ;kfofèk-I-}kjk vfèkd rFkk fØ;kfofèk-II-}kjk de

7. Match List I (Reaction) with List II (Product) and select the correct answer using the code given below the
lists :
lwph I (vfHkfØ;k) dks lwph II ¼mRikn½ ls lqesfyr dhft, rFkk lwfp;ksa ds uhps fn;s x;s dksM dk iz;ksx djds lgh mÙkj pqfu;s:
List I lwph I List II lwph II
P2O5
(P)   (1) A cyclic ester with O18 (O18 ds lkFk ,d pØh; ,LVj gS)


H
(Q)  (2) A cyclic amide (,d pØh; ,ekbM)


H
(R)  (3) A cyclic anhydride (,d pØh; ,ugkbMªkbM)

(S)  (4) A cyclic ester without O18 (O18 ds fcuk ,d pØh; ,LVj)

Codes ¼dksM½ :
P Q R S P Q R S
(A*) 3 1 4 2 (B) 3 4 1 2
(C) 4 3 2 1 (D) 4 1 3 2

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8. Match the column-I with column-II :
dkWye-I dks dkWye-II ls lqesfyr dhft, %
Column-I Column-II
dkWy e-I dkW ye -II

(A) + (p) CH3–CH2–OH

(B) (q) CH3–COOH

(C) (r)

(D) (s)

Ans (A)  s (B)  r (C)  p, q (D)  p

9. How many butyl bromide can be converted into Grignard reagent followed by their reaction with acid to form
n-Butane.
fdrus C;wfVy czksekbM fxzU;kj vfHkdeZd esa ifjofrZr gksdj vEy ls vfHkfØ;k djds n-C;wVsu cukrs gS \
Ans. 3
Sol. CH3—CH2—CH2—CH2—Br ,


H Fractional
10.  Total number of ester ‘M’ 
CH3CHClCOOH + CH3–CH2–OH   No. of Fractions ‘N’.
Distillation
( )
Report your answer as MN.

H
CH3CHClCOOH + CH3–CH2–OH 
 dqy ,LVj dh la[;k ‘M’ 
 dqy izHkkt ‘N’.
( )

viuk mÙkj ‘MN’ ds :i esa nhft,A


Ans. 21

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ChemINFO-1.5 Oxidation
Daily Self-Study Dosage for mastering Chemistry Aromatic side chain oxidation

Aromatic side chain oxidation


Strong oxidising agents like KMnO 4/H/ or K2Cr2O7/H/, oxidises benzylic carbon to – COOH group if benzylic
hydrogen or unsaturation is present.

General Reaction

No reaction

Note :- Tertiary butyl (CH3)3C– will not oxidise by oxidising reagent

KMnO / H
Ex.1

KMnO 4 / H / 
    Ex.2 
4

Memorize this theory as soon as you get the DPP. Revise it regularly and master this concept by practice.

KMnO / H
11. 
4
 Product

Product will be :

(A) (B*) (C) (D)

12. Which of the following reagent is suitable for the conversion of benzyl alcohol to benzoic acid
(A) K2Cr2O7/H+ / (B) KMnO4/H+ / (B) m–CPBA (D*) A and B both

13. Which of the following is oxidation product of given reaction.

KMnO / H

4

(A) (B) (C) (D*)

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KMnO 4 / H
14.    Product

Product is :

(A*) (B) (C) (D)

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DPP No. # 11 (JEE-MAIN)
Total Marks : 60 Max. Time : 40 min.

Single choice Objective ('–1' negative marking) Q.1 to Q.20 (3 marks, 2 min.) [60, 40]

1. is named as :

(A) 2, 3-Dimethylenebutanal (B) 3-Methyl-2-methylenebut-3-enone


(C*) 3-Methyl-2-methylenebut-3-enal (D) 2, 3-Dimethylenebutanone

dk uke gS %

(A) 2, 3-MkbesfFkyhuC;wVsuSy (B) 3-esfFky-2-esfFkyhuC;wV-3-bZuksu


(C*) 3-esfFky-2-esfFkyhuC;wV-3-bZuSy (D) 2, 3-MkbesfFkyhuC;wVsuksu

Sol. 3-Methyl-2-methylenebut-3-enal

Sol. 3-esfFky-2-esfFkyhuC;wV-3-bZuSy

2. How many structural isomers could be obtained from the alkane C6H14 ?
,Ydsu C6H14 ds fdrus lajpuk leko;oh lEHko gS \
(A) 4 (B*) 5 (C) 6 (D) 7

3. Reductive ozonolysis
An alkene (A)  A is

,d ,Ydhu (A) 


 A gS %

(A) (B) (C*) (D)

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Sol.

4. Acetaldehyde and Propyne can be distinguish by


,slhVSfYMgkbM vkSj izksikbu dks foHksfnr fd;k tk ldrk gSA
(A) NaHCO3 (B*) I2/NaOH (C) Lucas reagent D) neutral FeCl3
(A) NaHCO3 (B*) I2/NaOH (C) Y;qdkl vfHkdeZd (D) mnklhu FeCl3
Sol. Acetaldehyde and Propyne can be distinguish by Iodoform test.
,slhVSfYMgkbM vkSj izksikbu dks vk;ksMksQkeZ ijh{k.k }kjk foHksfnr fd;k tk ldrk gSA

5. Arrange following compounds in decreasing order of their dipole moment.


fn;s x, ;kSfxdksa ds f}/kqzo vk?kw.kZ dk ?kVrk gqvk Øe gS %
CH3—CH2—NO2 CH3—CH2—NH2 CH3—CH2—F CH3—CH2—CN
I II III IV

(A) IV > III >I > II (B) IV > I > III > II (C) I > III > IV > II (D*) I > IV > III > II
Ans. Decreasing order of dipole moment for given compounds
;kSfxdksa ds f}/kqzo vk?kw.kZ dk ?kVrk gqvk Øe fuEu gS %
I > IV > III > III

6. Identify which of the following does not show + m effect ?


fuEu esa ls dkSulk lewg + m izHkko iznf'kZr ugha djrk gS \
O O

|| ||
(A) –NH2 (B) –O (C)  NH  C  CH (D*)  C  NH  CH
3 3

O
||
Sol.  C  NH  CH3 do not contain lone pair or negative charge on first atom.

O
||
Sol.  C  NH  CH3 esa izFke ijek.kq ij ,dkdh bysDVªkWu ;qXe ;k _.kkRed vkos'k mifLFkr ugha gSA

7. The correct stability order of following is :


fuEu ds LFkkf;Ro dk lgh Øe gS %

(I) (II) (III) (IV)


(A) I > II > III > IV (B) III > IV > II > I (C) II > IV > III > I (D*) IV > III > II > I
Sol. Stability  resonance
 Hyperconjugation
length of conjugation is equal in all I, II, III & IV.
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g y- LFkkf;Ro  vuqukn
 vfrla;qXeu
lHkh I, II, III o IV esa la;qXeu dh yEckbZ leku gSA

8. Correct order of stability of given carbocation is :


fuEu dkcZ/kuk;uksa ds LFkk;hRo dk lgh Øe gS %

I II III
(A) I > III > II (B) I > II > III (C*) II > III > I (D) II > I > III

9. Which molecule have lowest pKb value?


dkSulk v.kq U;wure pKb eku j[krk gS\

(A) (B) (C) (D*)

NaHCO ( excess )
3 
10.      xCO 
 2

The number of CO2 molecules evolved in the above reaction, is :

NaHCO (
3  )
  xCO 
 2

fuEufyf[kr vfHkfØ;k esa fdrus eksy CO2 v.kq fudysxsaA

(A*) 3 (B) 4 (C) 5 (D) 6

Sol. The group –SO 3H, –COOH and the nitrophenols (o, p etc.) are stronger acids than H 2CO3, so only these
acidic groups can evolve CO2 on reaction with NaHCO3

11. Using anhydrous AlCl3 as catalyst, which one of the following reaction produce ethylbenzene (PhEt)?
mRizsjd futZyh; AlCl3 dh mifLFkfr esa fuEu esa ls fdldh fØ;k }kjk ,fFkycsUthu (PhEt) curk gS ?
(A) H3C – CH2OH + C6H6 (B) CH3 – CH == CH2 + C6H6
(C*) C2H5Cl + C6H6 (D) H3C – CH3 + C6H6

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12. The treatment of benzene with isobutene in the presence of sulphuric acid gives :
(A) isobutyl benzene (B*) tert-butyl benzene (C) n-butyl benzene (D) no reaction
csUthu dh lY¶;wfjd vEy dh mifLFkfr esa vkblksC;wVhu ds lkFk fØ;k ij curk gS %
(A) vkblksC;qfVy csUthu (B*) r`rh;d-C;qfVy csUthu (C) n-C;qfVy csUthu (D) vfHkfØ;k ugha

Sol. Friedel Craft reaction.

13. Which of the following organic chloride will not give a Friedel-Craft alkylation product when heated with
benzene and AICI3
fuEu esa ls dkSulk dkcZfud DyksjkbM cSUthu vkSj AICI3 ds lkFk xeZ djus ij ÝhMy&Øk¶V ,fYdyhdj.k vfHkfØ;k
ugha nsxkA
(A) (CH3)3 CCI (B) CH2 = CHCH2CI (C) CH3CH2CI (D*) CH2 = CHCl
Sol. In vinyl chloride lone pair of Cl atom take part in conjugation so partial double bond character between C–Cl
bond.
g y- foukby DyksjkbM esa Dyksjhu dk ,dkdh bysDVªkWu la;qXeu esa Hkkx ysrk gS blfy, C–Cl ca/k esa f}ca/k ds y{k.k gksrs gSA

14. When benzene reacts with HNO3/H2SO4 structure of intermediate formed is :


tc csUthu dh fØ;k HNO3/H2SO4 ds lkFk dh tkrh gS rc e/;orhZ D;k gksxk &

(A) (B) (C*) (D)


Sol. HNO3 + H2SO4  N O + H2O + HSO4–
2

15. Arrange the following compounds in the order of decreasing reactivity towards electrophilic substitution
reaction.
bysDVªkWu Lusgh izfrLFkkiu vfHkfØ;k ds izfr fuEu dks fØ;k'khyrk ds ?kVrs gq, Øe esa O;ofLFkr dhft,A

(A) V > IV > III > II > I (B*) I > II > III > V > IV
(C) I > II > IV > III > V (D) I > III > IV > II > V
Sol. Rate of electrophilic substitution reaction  Stability of arenium ion.

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16. A particular form of tribromobenzene forms three possible mononitro Bromo-benzenes the structure of
compound is :

(A) (B*) (C) (D) Both B and C

,d VªkbZczksekscsathu] rhu lEHko eksuksukbVªks czksekscsathu cukrh gS rks ;kSfxd dh lajpuk gksxhA

(A) (B*) (C) (D) B rFkk C nksuksa

Sol. conc. HNO  conc. H SO



3

2 4

17. (X) [Y]

Y is

(A) (B) (C*) (D)

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18. P Q

The products Q is : mRikn Q gS&

(A) (B*) (C) (D)

Sol.

conc. HNO conc. H SO


3 2 4 Cl 2 / FeCl 3
19.     
Heat

  X    Y

The product Y is :
(A) p-chloro nitrobenzene (B*) m-chloro nitrobenzene
(C) o-chloro nitrobenzene (D) o,p-dichloro nitrobenzene

conc. HNO conc. H SO


3 2 4 Cl 2 / FeCl 3
    
Heat

  X    Y

mRikn Y gS %
(A) p-Dyksjks ukbVªkscsUthu (B*) m-DyksjksukVªkcs sUthu
(C) o-Dyksjks ukbVªkcs sUthu (D) o,p-MkbZDyksjks ukbVªkscUs thu

conc. HNO conc. H SO


3 2 4 Cl / FeCl
Sol.    
Heat

  2  
3

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20. 

For above reaction which of the following reaction condition is suitable.


(A) CH3–CH2–CH2–Cl / AlCl3 (B) / AlCl3 followed by NH2–NH2 / KOH

(C) CH2=CH2–CH2–Cl / AlCl3 (D*) CH2=CH–Cl / AlCl3 followed by H2 / Ni



mijksDr vfHkfØ;k ds fy, fuEu esa ls dkSulh vfHkfØ;k ifjfLFkfr mfpr gS \


(A) CH3–CH2–CH2–Cl / AlCl3 (B) / AlCl3 blds i’’'pkRk~ NH2–NH2 / KOH

(C) CH2=CH2–CH2–Cl / AlCl3 (D*) CH2=CH–Cl / AlCl3 blds i’’'pkRk~ H2 / Ni

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