ORGANIC CHEMISTRY

TARGET : JEE (Main + Advanced) 2016

Course : VIJAY (JR) NO. 21

This DPP is to be discussed in the week (16-11-2015 to 21-11-2015)

1. Course of the week as per plan :
2. Course covered till previous week :
3. Target of the current week :
4. DPP Syllabus : Organic reaction mechanisms-II
DPP No. # 21 (JEE-MAIN)
Total Marks : 33 Max. Time : 22 min.

Single choice Objective ('–1' negative marking) Q.1 to Q.22 (3 marks, 2 min.) [33, 22]

Answer key
1. (C) 2. (B) 3. (B) 4. (C) 5. (A) 6. (C) 7. (B)
8. (C) 9. (B) 10. (D) 11. (B) 12. (B) 13. (D) 14. (B)
15. (B) 16. (A) 17. (C) 18. (C) 19. (D) 20. (A*) 21. (A)
22. (B)

1. 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

2. Arrange the following compounds in the order of decreasing reactivity towards electrophilic substitution
reaction.
fuEUk ;kSfxdksa dk bysDVªkWu Lusgh izfrLFkkiu vfHkfØ;k ds izfr fØ;k'khyrk dk ?kVuk gqvk lgh Øe gSA

[Ref. SDK Sir]

(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.
bysDVªkWu Lusgh izfrLFkkiu vfHkfØ;k dh nj ,sjsfu;e vk;u dk LFkkf;Ro

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 conc. HNO conc. H SO
3 2 4 Cl 2 / FeCl 3
3.     
Heat

  X    Y

The product Y is : [AIIMS 2000]

(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 % [AIIMS 2000]

(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


4. Which of the following carbocations is expected to be least stable?

fuEu esa ls dkSulk dkcZ/kuk;u lEHkor% U;wure LFkk;h gS ?

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

Sol. No hyperconjugation effect of CH3 group in

esa CH3 lewg dksbZ vfrl;qXeu izHkko ugha n'kkZrk gSA

5. Arrange the following in decreasing order of reactivity towards bromination

czksehuhdj.k ds izfr fuEu dks fØ;k'khyrk ds ?kVrs gq, Øe esa O;ofLFkr dhft,A [Ref. SDK Sir]

(A*) ii > i > iv > iii (B) iv > ii > i > iii (C) i > ii > iii > iv (D) iv > iii > ii > i

Sol. Reactivity towards bromination  Stability of arenium ion.

czksehuhdj.k ds izfr fØ;k'khyrk  ,sjsfu;e vk;u dk LFkkf;Ro
6. 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 ? [AIPMT 2004]
(A) H3C – CH2OH + C6H6 (B) CH3 – CH == CH2 + C6H6
(C*) C2H5Cl + C6H6 (D) H3C – CH3 + C6H6

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7. 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. fÝfMy Øk¶V vfHkfØ;k

8. (X) [Y]

Y is : Y gS %

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

9. P Q

The products Q is : mRikn Q gS&

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

Sol.

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10. 

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

11. Phenylbenzoate when treated with Br2 / Fe gives ? [Aromatic]

QsfuycsUtks,V dks Br2 / Fe ds lkFk mipkfjr djus ij fuEu esa ls dkSulk ;kSfxd izkIr gksrk gS\ [G.R]

(A) (B*)

(C) (D)

12. Which is the most likely group for substituent 'X' based on the relative rate factors for chlorination in the given
compound. [Aro 2.12 (M1)]
fn;s x;s ;kSfxd dh Dyksjhuhdj.k vfHkfØ;k dh nj dks izHkkfor djus okyk fuEu ls dkSu lk lewg izfrLFkkih X ds fy;s mi;qDr
gksxk \

(A) – CF3 (B*) – C(CH3)3 (C) – CH3 (D) – CH = O

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 ;qXe la;qXeu esa Hkkx ysrk gS blfy, C–Cl ca/k esa vkaf'kd f}ca/k ds y{k.k
gksrs gSA

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14. The end product of following sequence of reactions is
fuEufyf[kr vfHkfØ;k vuqØe esa vfUre mRikn gksxk \

Cl , h PhH, AlCl
3
2   
 
(1) ( 2)

(A) (B*)

(C) (D)

2 Cl , h 3 PhH, AlCl
Sol. Ph – CH3 (
1)
 Ph – CH – Cl  
2
  Ph – CH2 – Ph
Friedel craft
reaction

15. The end product of following sequence of reactions is [Refer RGP Sir]
fuEufyf[kr vfHkfØ;k vuqØe esa vfUre mRikn gksxk \

AlCl NH NH / KOH  Se' / 

3   2 2  H 
+ 
    

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

Sol.

OH

AlCl
3 NH2 NH2 / KOH
    H iquZfoU;kl 
H  Se ' / 
 
+  
 

16. Which of the following is not the correct route to prepare compound 'X' ? [Aro 3.4 (M2)]
fuEu esa ls fdl vfHkfØ;k esa ;kSfxd 'X' dk fuEkkZ.k ugha gksrk gS \

X =

(A*) + 

(B) (C) +

(D)

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Sol.(A) is highly deactivated due to electron with drawing nature of NO 2.

es NO2 dh bysDVªkWu vkd"khZ izd`fr ds dkj.k ;g mPp fuf"Ø;dkjh gksrk gSA

17. The product of the following reaction is :

fuEu vfHkfØ;k esa mRikn gksxk \
AcCl / AlCl
3 3 AcCl / AlCl Br / Fe
            2 


(A) (B)

(C*) (D)

Sol. CH COCl / AlCl

3 3
      

Phenyl ring is o/p directing

Qsfuy oy; o/p funsZ'kh gksrh gSA
18. What is the relationship between the moelcues in the following pairs ? RGP Sir
fuEufyf[kr v.kqvksa ds eè; D;k lacaèk gS\

and rFkk

(A) Enantiomers (B) Diastereomers (C*) Identical (D) Structural isomers

(A) izfrfcEc:ih (B) foofje:ih (C*) le:ih (D) lajpukRed leko;oh

19. Which of following acid give positive Tollen’s reagent test ?

fuEUk esa ls dkSulk vEy èkukRed VkWysu vfHkdeZd ijh{k.k nsrk gS \

(A) (B) (C) (D*) HCO2H

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20. RGP Sir

Identify most acidic hydrogen present in the above compound :

mijksDr ;kSfxd esa fuEu esa ls dkSulk gkbMªkstu ijek.kq lokZfèkd vEyh; gSA
(A*) a (B) b (C) c (D) d

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

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

NaHCO (
3  )
  xCO 
 2

fuEufyf[kr vfHkfØ;k esa fdrus 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
lewg –SO3H, –COOH o ukbVªksfQukWy (o, p bR;kfn ) H2CO3 dh rqyuk es izcyre vEy gS blfy, dsoy ;g vEyh; lewg
NaHCO3 ds lkFk vfHkfØ;k ij CO2 eqDr djrk gSA

22. The most acidic species is :

lcls vf/kd vEyh; Lih'kht gS % [Ref. : VPM madam (Ka) Test-12-3-06-GRST-JM]

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

Sol.

¼,sjksesfVd½

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