Jp Xii Organic Chemistry (16).pdf

ORGANIC CHEMISTRY

TARGET : JEE (Main + Advanced) 2016 NO. 20

Course : VIJETA (JP)

DPP No. # 20 (JEE-ADVANCED) 1. 6. 8. 11.

(A,B,C,D) (i). (C*) A - p ; B - p, (A*)

2. (B,C,D) 3. (ii). (A*) (iii). (B*) r ; C - p, q, s ; D - p, q, s. 12. (C*) 13.

(A,B)

4. 7. 9. 14.

(A*)

(B,C,D) (D*) 3 (C*)

5.

(B,D)

10.

43

This DPP is to be discussed in the week (13.07.2015 to 18.07.2015)

DPP No. # 20 (JEE-ADVANCED) Total Marks : 58

Max. Time : 36 min.

Multiple choice objective ('–1' negative marking) Q.1 to Q.5 Comprehension ('–1' negative marking) Q.6 (i to iii) Matching List Type (One Option Correct) ('–1' negative marking) Q.7 Match the Following (no negative marking) Q. 8 Integer Type Questions Q.9 to Q.10 ChemINFO : 4 Questions ('–1' negative marking) Q.11 to Q.14

1.

marks, marks, marks marks, marks, marks,

2 2 2 6 2 2

min.) min.) min.) min.) min.) min.)

[20, 10] [09, 06] [03, 02] [08, 06] [06, 04] [12, 08]

Following graph between G and reaction progress in for/can be : G ,oa

2.

(4 (3 (3 (8 (3 (3

vfHkfØ;k ds e/; fuEufyf[kr vkjs[k dkSulh vfHkfØ;kvksa ds fy, lgh gksxk

(A*) SN1 reaction (C*) Aromatic electrophilic substiution (A*) SN1 vfHkfØ;k

(B*) E1 reaction (D*) Electrophilic addition reaction (B*) E1 vfHkfØ;k

(C*) ,jksesfVd

(D*) bysDVªksu

bysDVªku Lusgh izfrLFkkiu vfHkfØ;k

Lusgh ;ksxkRed vfHkfØ;k

Observe the following sequence of reactions. W hich statement/s is/are correct about these reaction. X, Y and Z are the major products obtained. CH3 CH3 | | AgOH  CH3 I       PhCH 2  CH  CH 2  N : ( 3) ( 2) (1) | CH3

(Z)

(Y)

(A) Product ‘Y’ is an optically active compound (B*) X and Z are positional isomers (C*) Step-1 is SN 2 reaction, step-4 is electrophilic addition reaction (D*) Step-3 and step-5 are elimination reactions Corporate Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.)-324005 Website : www.resonance.ac.in | E-mail : [email protected] Toll Free : 1800 200 2244 | 1800 258 5555| CIN: U80302RJ2007PTC024029

PAGE NO.- 1

fuEu fyf[kr vfHkfØ;k Øe esa lgh dFku gS tgk¡ X, Y rFkk Z eq[ ; mRikn gS& CH3 CH3 | | PhCH 2  CH  CH 2  N : | CH3

CH I (1)

3    

AgOH ( 2)

(Z) (A) mRikn ‘Y’ ,d izdkf'kd lfØ; ;kSfxd gS (B*) X vkSj Z fLFkfr leko;oh gS (C*) in -1 SN 2 vfHkfØ;k rFkk in -4 bysDVªkW u (D*) in -3 rFkk in -5 foyksi u vfHkfØ;k gS

Sol.

(Y)

Lusgh ;ksxkRed vfHkfØ;k gS

CH3 CH3 | | PhCH 2 CH  CH 2  N : | CH3

CH3 | N(CH3) 3 + H 2O + Ph  CH2  C  CH2 ( X)

CH3 | Ph  CH2  C  CH3 | Cl (Y) 3.

 ( 3)

  

Ag I +

CH3 | Ph  CH  C  CH3 (Z )

When neopentyl alcohol is treated with H2SO4 a mixture of two alkenes (85:15) is formed. Which statement/ s is / are correct about these alkenes. (A*) Both give same major product with HBr. (B*) Both give different products (major) with HBr / R2O2 / light. (C) The alkene which is formed in 85% concentration has higher heat of hydrogenation than the other one obtained in 15% concentration. (D) Both give same product on ozonolysis. tc fu;ksisfUVy ,Ydksgy dks H2SO4 ds lkFk mipkfjr djrs gS rks nks ,fYduks (85:15) dk feJ.k curk gSA bu ,fYduksa ds

lUnHkZ esa fuEUk esa ls dkSulk@dkSUkls dFku lgh gS\ (A*) nksuksa HBr ds lkFk leku eq[; mRikn nsrs gSA (B*) nksauksa HBr / R2O2 / iz’dk’'k ds lkFk fHkUUk mRikn (eq[;) nsrs gSA (C) ,fYdu tks 85% lkUnzrk esa curh gS] ;g 15% lkUnzrk esa izkIr ,d vU; ,fYdu ls mPp gkbMªkt s uhdj.k dh Å"ek j[krh gSaA (D) nksuksa vkstksuhvi?kVu ij leku mRikn nsrs gSA Sol.

CH3 | CH3  C  CH2  OH | CH3 Corporate Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.)-324005 Website : www.resonance.ac.in | E-mail : [email protected] Toll Free : 1800 200 2244 | 1800 258 5555| CIN: U80302RJ2007PTC024029

PAGE NO.- 2

KOH  

4.

Which of the following is/are True for the above reaction

mDr vfHkfØ;k ds lanHkZ esa fuEu esa ls dkSulk@dkSuls dFku lR; gS@gSa \ (A) Deuterium exchange is not seen during this reaction if carried out in D 2O

bl vfHkfØ;k esa M~;wVsfj;e fofue; ugha gksrk gS] ;fn ;g vfHkfØ;k D2O esa dh tkrh gSA (B*) Reaction occurs in two steps.

vfHkfØ;k nks inksa esa lEiUu gksrh gSA (C*) HO– acts as a base. HO– {kkj dh rjg dk;Z djrk gSA (D*) Anion formed as intermediate is Aromatic.

e/;orhZ ds :i esa cuus okyk _.kk;u ,sjkseSfVd gSA 5.

The correct statements about the following reaction are :

[Hint : Al2O3 gives saytzeff's product without any rearrangment]

(A) The product P is

(B*) The product Q is

(C) The product R is

(D*) The compound

gives product

(P) on treatment with conc. H2SO4 as well as with Al2O3/ Corporate Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.)-324005 Website : www.resonance.ac.in | E-mail : [email protected] Toll Free : 1800 200 2244 | 1800 258 5555| CIN: U80302RJ2007PTC024029

PAGE NO.- 3

fuEu vfHkfØ;k ds ckjs esa lgh dFku gksxsaA

[ladsr: Al2O3 fcuk

fdlh iquZfoU;kl ds lsV~tsQ mRikn nsrk gS]

(A) mRIkkn P

(B*)

gSA

(C) mRikn R

gSA

gSA

(D*) ;kSfxd

lkUnz H2SO4 vkSj Al2O3/ds lkFk mipkfjr djus ij mRikn (P) nsrk gSA

Conc . H SO

Sol.

mRikn Q

O

4   2 

3  



Zn / H2O

(Q)

O

3  

Zn / H2O

O

3  

Zn / H2O

(Q)

O

3  

Zn / H2O

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PAGE NO.- 4

6.

Comprehension # Deuterium is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. T he chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C–D bond is slightly (1.2 kcal/mol or 5.0 KJ/mol) stronger than C–H bond. Reaction rates tend to be slower if a C–D bond (as compared to a C–H bond) is broken in a rate limiting step. This effect on the rate is called a kinetic isotopic effect. Observe the following reactions (I)

(II)

KOH, alcohol    

+

KOH, alcohol    

+



(III)

H2 O / acetone   

(IV)

H2O / acetone   

+



+



(i).

Find out the correct statement about I and II reaction (for elimination product) (A) For elimination product rate of formation of CH2= CH–CH3 and CD2= CH–CD 3 is same. (B) Rate of formation of CD2= CH–CD3 is greater than rate of formation of CH2= CH–CH3 (C*) Rate of formation of CH2= CH–CH3 is greater than rate of formation of CD2=CH–CD3 (D) We can not predict which will form faster.

(ii).

Find out correct statement about I and II reaction (for substitution product) (A*) Rate of formation of

and

is almost same.

(B) Rate of formation of

is geater than

formation.

(C) Rate of formation of

is very much greater than formation of

.

(D) We can not predict which will form faster. (iii).

Find out correct statement about III and IV reaction (A) CH2=CH–CH3 and CD2=CH–CD3 are formed at same rate by E2 mechanism (B*) CH2=CH–CH3 and CD2=CH–CD3 are formed at same rate by E1 mechanism (C)

is formed faster than

(D)

is formed 7 times faster than

by SN1 mechanism

by SN1 mechanism.

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PAGE NO.- 5

6.

vuqP Nsn # M~;wVsfj;e gkbMªkstu ds ukfHkd esa izksVkWu rFkk U;wVªksu ds lkFk nzO;eku la[;k 2, ds gkbMªkstu dk leLFkkfud gSA M~;wVsfj;e dk jlk;u gkbMªkstu ds jlk;u ds yxHkx leku gksrk gS] blds ctk; dh C–D cU/k (1.2 kcal/mol ;k 5.0 KJ/mol) C–H cU/k dh vis{kk de izcy gksrk gSA vfHkfØ;k nj de gksus dh lkEkF;Z j[krh gS] ;fn C–D cU/k (C–H cU/k dh rqyuk eas ) nj lhekUr in esa VwVrk gSA nj ij ;g izHkko xfrd leLFkkfud izHkko dgykrk gS A fuEu vfHkfØ;kvksa dk voyksdu dhft,A (I)

(II)

KOH, alcohol    

KOH, alcohol    

+

+



(i).

(ii).

(III)

H2 O / acetone   

(IV)

H2 O / acetone   





+

+

I rFkk II vfHkfØ;k (foyksiu mRikn ds fy,) ds ckjs eas lgh dFku crkb;saA (A) CH2= CH–CH3 rFkk CD2= CH–CD3 ds fuekZ.k dh nj foyksiu mRikn (B) CD2= CH–CD3 ds fuekZ.k dh nj CH2= CH–CH3 ds fuekZ.k dh nj ls (C*) CH2= CH–CH3 ds fuekZ.k dh nj CD2=CH–CD3 ds fuekZ.k dh nj ls (D) ge ;g Kkr ugh dj ldrs gS fd dkSulk mRikn rhozre cusxkA I rFkk II vfHkfØ;k (izfrLFkkiu (A*)

ds fy, leku gksrh gSA vf/kd gksrh gSA vf/kd gksrh gSA

mRikn ds fy,) ds ckjs eas lgh dFku crkb;saA

rFkk

ds fuekZ.k dh nj izk;% leku gksrh gSA

(B)

ds fuekZ.k dh nj

ds fuekZ.k dh nj ls vf/kd gksrh gSA

(C)

ds fuekZ.k dh nj

ds fuekZ.k dh nj ls cgqr&cgqr vf/kd gksrh gSA

(D) ge

;g Kkr ugh dj ldrs gS fd dkSulk mRikn rhozre cusxkA

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PAGE NO.- 6

(iii).

III rFkk IV vfHkfØ;k

ds fy, lgh dFku crkb,A

(A) CH2=CH–CH3 RkFkk CD2=CH–CD3 leku

nj ij E2 fØ;kfof/k }kjk curs gSA

(B*) CH2=CH–CH3 RkFkk CD2=CH–CD3 leku

7.

(C)

,

(D)

,

nj ij E1 fØ;kfof/k }kjk curs gSA

dh vis{kk SN1 fØ;kfof/k }kjk rsth curk gSA

dh vis{kk 7 xquk S N1 fØ;kfof/k }kjk rsth curk gSA

Match List I (Reaction) with List II (Mechanism) and select the correct answer using the code given below the lists : lwph-I (vfHkfØ;k) dks lwph-II (fØ;kfof/k) ds lkFk lqesfyr dhft, rFkk uhps fn;s x;s dksM+ksa dk mi;ksx djrs gq, lgh mÙkj

dk p;u dhft,A List I

List II

lwph -I

lwp h-II

(P)

(Q)

(1) SN1

CH 3 | CH3  C  Br H2O   | CH3

(2) SN2

Isopropylalcohol  KOH     

(R)

(3) E1



Conc. H SO

2 4  

(S)

(4) E2



Codes : (A) (C)

8.

P 1 1

Q 2 2

R 4 4

S 3 3

(B) (D*)

P 2 2

Q 1 1

R 3 4

S 4 3

Match the reactions of column I with the characteristics mentioned in column II. Column I Column II (Reaction) (Characteristics)

O F || | (A) Ph — C — CH2 — CH — CH3

(B)

H SO

4 2   



Base,   

(p) Regioselective reaction

(q) Stereospecific reaction

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PAGE NO.- 7

(C)

(D)

alc. KOH   

(r) Rearrangement reaction



MeONa  

(s) Bimolecular reaction

dkWye-I esa nh xbZ vfHkfØ;k dk dkWye-II esa fn;s x;s yk{kf.kd xq.k ls feyku dhft,A dkWy e-I dkW ye -II ( vfHkfØ;k ) (yk{kf.kd xq. k ) O F || | (A) Ph — C — CH2 — CH — CH3

(B)

(C)

(D)

Ans.

A-p;

Base,   

(p) fjft;kslysfDVo

H2SO4   

(q) f=kfoe



alc. KOH    

MeONa  

vfHkfØ;k

fof'k"V vfHkfØ;k

(r) iquZfoU;kl

vfHkfØ;k

(s) f}vkf.od

vfHkfØ;k

B - p, r ; C - p, q, s ; D - p, q, s.

Alc KOH    Total number of possible alkenes are :

9.

¼dqy lEHko ,Ydhu mRikn dh la[;k gksxh½ [RMC 15.9 (M1)] Ans.

Sol.

3

Alc KOH    E 2 mech.

+

+

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PAGE NO.- 8

10.

Report your answer as

vius mÙkj dks fuEu çdkj vafdr djksA Ans.

43

Sol.

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PAGE NO.- 9

ChemINFO-2.2

Chemistry in Every day life

Daily Self-Study Dosage for mastering Chemistry

Catalytic hydrognation

The chemical subtances that decrease or reduce or neutralise the gastric acidity and raise the pH to appropriate level are called antacids. These are usually NaHCO3 (Sodiumbicarbonate) or mixture of Aluminum and Magnesium hydroxide. Sodium bicarbonate can make the stomach alkaline and increase the production of even more acid. Metal hydroxides and silicates are better alternatives because of being insoluble, these donot increase the pH above neutrality. These controls only symptoms and not the cause. The cause of hyperacidity is due to which a chemical Histamine stimulates the secretion of pepsin and hydrochloric acid in the stomach. The drugs Cimetidine (Tegamet), Ranitidine (Zantac) prevent the interaction of Histamine with the receptors present in stomach wall . This resulted in release of lesser amount of acid . Recently Omeprazole and Lansoprazole have been synthesised in order to give quick relief from acidity. They also prevent the formation of acid in stomach.

,

,

Memorize this theory as soon as you get the DPP. Revise it regularly and master this concept by practice. 11.

Which of the following excessive antacid will increases the acidity : (A*) NaHCO3

12.

(D) MgCO3

(B) Cimetidine

(C*) Histamine

(D) Seldane

Which of the following drug prevents the interaction of histamine with receptors present in stomach wall. (A*) Ranitidine

14.

(C) Al(OH)3

Which of the following stimulates the secretion of pepsin and hydrochloric acid in stomach. (A) Ranitidine

13.

(B) Mg(OH)2

(B) Histamine

(C) NaHCO3

(D) Mg(OH)2

(C*) Mg(OH)2

(D) KOH

Which of the following is common antacid : (A) NaOH

(B) Ca(OH)2

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PAGE NO.- 10

ChemINFO-2.2

Chemistry in Every day life

Daily Self-Study Dosage for mastering Chemistry

Catalytic hydrognation

,sls jlk;u ftudk mi;ksx vek'k; dh xSfLVªd vEyrk dks de djus vFkok mnklhu djus ds fy, fd;k tkrk gS rFkk vek'k; dh pH Lrj dks mi;qDr Lrj rd c<+kus ds fy, fd;k tkrk gS] mUgssa izfrvEy dgrs gSaA lkekU;r;k NaHCO3 (lksfM;e ckbZdkcksZusV), vFkok ,Y;wfefu;e rFkk eSaXuhf'k;e gkbMªksDlkbM ds feJ.k dk mi;ksx izfrvEy dh rjg fd;k tkrk gSA lksfM;e ckbZdkcksZusV vek'k; dks {kkjh; dj nsrk gS rFkk vf/kd mRiknu dks izzsfjr djrk gSA /kkfRod gkbMªksDlkbM rFkk flfydsV~l ,d cgqr vPNs fodYi gSa D;ksafd ;g v?kqyu'khy voLFkk esa ik;s tkrs gSa] ftlds ifj.kkeLo:i ;g vek'k; dh pH dks mnklhurk ls vkxs c<+us ugha nsrs gSaA mijksDr nksuksa gh mipkj dsoy jksx ds y{k.kksa dks fu;af=kr djrs gSa] dkj.k dks ughaA izfrvEyrk ds mipkj esa eq[; ifjroZu ml [kkst ds ckn gqvk] ftlds vuqlkj jlk;u fgLVkfeu] vek'k; esa isIlhu rFkk gkbMªksDyksfjd vEy ds L=ko.k dks mn~nhfir djrk gSA flesfVMhu ¼VsxkesV½( jsuhfVMhu ¼tSuVSd½ uked vkS"kfèk;k¡ vek'k; dh nhokj esa fLFkr xzkgh;ksa ds lkFk fgLVkehu dh vU;ksU;fØ;k dks jksdrh gSA ftlds ifj.kkeLo:i vEy dh de ek=kk L=kfor gksrh gSA orZeku le; esa vEyrk ls rqjUr funku ikus ds fy, vksesizktksy rFkk ySUlksizktkWy uked la'ysf"kr vkS"kf/k;ksa dk mi;ksx fd;k tkrk gS tks vek'k; esa vEy ds fuekZ.k dks jksdrh gSA

,

,

Memorize this theory as soon as you get the DPP. Revise it regularly and master this concept by practice. 11.

fuEu esa ls dkSulk izfrvEy vf/kd ek=kk esa ysus ij] vek'k; dh vEyrk dks c<+k nsrk gS : (A*) NaHCO3

(B) Mg(OH)2

(C) Al(OH)3

(D) MgCO3

12.

fuEu esa ls dkSu vek'k; esa isIlhu rFkk gkbMªksDyksfjd vEy ds L=kko.k dks mn~nhfir djrk gS \ (A) jsfufVMhu (B) flesfVMhu (C*) fgLVkehu (D) lSYMsu

13.

fuEu esa ls dkSulh vkS"k/kh vek'k; nhokj esa fLFkr xzkgh;ksa ds lkFk fgLVkehu dh vU;ksU; fØ;k dks jksdrh gS \ (A*) jsfufVMhu (B) fgLVkehu (C) NaHCO3 (D) Mg(OH)2

14.

fuEu esa ls dkSulk lkekU; izfrvEy gS ? (A) NaOH

(B) Ca(OH)2

(C*) Mg(OH)2

(D) KOH

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PAGE NO.- 11