Jp Xii Organic Chemistry (03).pdf

ORGANIC CHEMISTRY

TARGET : JEE (Main + Advanced) 2016 Course : VIJETA (JP)

Date : 13-04-2015

DPP DAILY PRACTICE PROBLEMS

NO. 03 & 04

TEST IN FORMATION DATE : 19.04.2015

SCHOLARSHIP TEST

Syllabus : Complete IX Syllabus

This DPP is to be discussed in the week (13-04-2015 to 18-04-2015)

DPP No. # 03 (JEE-MAIN) Total Marks : 60

Max. Time : 40 min.

Single choice Objective ('–1' negative marking) Q.1 to Q.20

1.

(3 marks, 2 min.)

Which of the following compound does not possess C 2 axis of symmertry ? fuEu esa ls dkSuls ;kSfxd esa C2 lefefr dk v{k mifLFkr ugha gS \

(A)

(B)

(C*)

(D)

Sol.

Compound

g y-

;kSfxd

2.

Which of the following compound will show stereoisomerism ? (A*) 1 - Phenylethanamine (B) Phenyl chloroethanoate (C) 3-Chloro-3-ethynylpenta- 1,4-diyne (D) 3-Methylbutanoic acid fuEu esa ls dkSulk ;kSfxd f=kfoe leko;ork n'kkZrk gS ? (A*) 1 - Qsfuy,Fksusehu (B) Qsfuy Dyksjks,FksukW,V (C) 3-Dyksjks-3-,FkkbfuyisUVk- 1,4-MkbZvkbu (D) 3-esfFkyC;wVsukWbd vEy Easy

Sol.

[60,4 0]

(A)

has C3 and C3/2 axis of symmetry but no C2 axis of symmetry..

esa C3 rFkk C3/2 lefefr dk v{k mifLFkr gS ysfdu C2 lefefr dk v{k mifLFkr ugha gSA

(B)

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PAGE NO.- 1

(C)

(D)

Only (A) is optical active compound so it shows stereoisomerism. dsoy ;kSfxd (A) izdkf'kd lfØ; ;kSfxd gS blfy, ;g f=kfoe leko;ork n'kkZrk 3.

4.

gSA

Chiral molecules are those which are : (A) Superimposable on their mirror image (C) Having no mirror images

(B*) Not superimposable on their mirror image (D) Capable of showing geometrical isomerism

os v.kq fdjSy v.kq gksrs gS ftuesa % (A) muds niZ.k izfrfcEc v/;kjksfir gksrs gS (C) tks niZ.k izfrfcEc ugha j[krs gSa

(B*) muds niZ.k izfrfcEc v/;kjksfir ugha gksrs (D) T;kfefr leko;ork n'kkZus esa l{ke gksA

gSa

Which of the following has asymmetric carbon atom ?

fuEu esa ls fdlesa vlefer dkcZu ijek.kq gS \ (A)

5.

(C)

(D)

The structure of (2R, 3R) CH3CH(OH)CH(OH)COOH is (2R, 3R) CH3CH(OH)CH(OH)COOH dh lajpuk gS &

(A*)

6.

(B*)

(B)

(C)

(D)

Among the following amino acids the R-enantiomer is represented by :

uhps fn;s x;s ,ehuks vEy esa R-izfrfcEc leko;oh gS:

(A)

7.

(B*)

(C)

(D)

Which of the following is the lowest molecular weight hydrocarbon which is chiral. (A*) 3-Methylhexane (B) 2, 4-Dimethylpentane (C) 2, 2-Dimethylpentane (D) 3, 3-Dimethylpentane

fuEu esa ls dkSu U;wure v.kq Hkkj ;qDr gkbMªksdkcZu tks fd fdjSy gSA (A*) 3-esfFkygsDlsu (B) 2, 4-MkbZesfFkyisUVsu (C) 2, 2-MkbZesfFkyisUVsu 8.

(D) 3, 3-MkbZesfFkyisUVsu

Which among the following compound has (L) configuraiton ? fuEu esa ls fdl ;kSfxd dk (L) foU;kl gS\

(A)

(B*)

(C)

(D)

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9.

Which of the following compound posses plane of symmetry :

fuEu esa ls dkSulk ;kSfxd leferh dk ry j[krk gS :

(A)

(B)

(C*)

(D)

10.

The above pair has relation (A) Enantiomers

(B) Diastereomers

mijksDr ;kSfxdks dk ;qXe fuEu esa ls fdl izdkj lEcfU/kr gSa \ (A) izfrfcEc :ih (B) foofje :ih 11.

.

(C) Homologous

(D*) Identical

(C) ltkrh;

(D*) le:i

;kSfxd

A compound was having [] = 40.3º in polarimeter experiment in clockwise direction what can be the structure is : ,d ;kSfxd dk [] = 40.3º gS ftls iksysjhehVj iz;ksx ls nf{k.kkorZ fn'kk esa Kkr fd;k x;k gSA vr% bldh lajpuk gksxhA

(A)

(B)

(C)

(D*)

12.

has optical rotation –45°, so optical rotation of

(A) + 45°

(B) 0°

(C) – 45°

will be

(D*) Can not be predicted

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dk izdkf'kd ?kw.kZu – 45° gS rks

(A) + 45° 13.

(B) 0°

dk izdkf'kd ?kw.kZu gksxkA

(C) – 45°

(D*) dqN

dgk ugha tk ldrk A

In which of the following spatial representation of group/atoms is different from the given strucuture P.

P=

dkSuls fodYi esa fn;s x;s lewgksa ,oa ijek.kqvksa ds f=kfoe vfHkfoU;kl lajpuk P ls fHkUu gSA

P=

(A)

14.

(B)

If the optical rotation produced by

(C)

(D*)

is +36º, then the optical rotation produced by

will be :

;fn

(A) – 36º 15.

}kjk mRiUu izdkf'kd ?kw.kZu +36º gS rks

(B*) 0º

}kjk mRiUu izdkf'kd ?kw.kZu gksxk&

(C) + 36º

(D) Unpredictable vKkruh;

(C)

(D)

Which of the following is a meso compound ? fuEu esa ls dkSu ehlks ;kSfxd gS ?

(A*)

(B)

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16.

The following two compounds are

fuEu ;qXe ds e/; lEc/k gSA

& (A*) Enantiomers (A*) izfrfcEc :i leko;oh 17.

(C) Identical (C) le:i

(D) No relation (D) dksbZ lEc/k ugh

Which of the following does not represent D-Lactic acid : fuEu esa ls dkSulk D-ysfDVd vEy dks ugha n’kkZrk gS

(A)

Sol.

(B) Diastereomers (B) foofje leko;oh

(B*)

(C)

(D)

Moderate

(A)

(B)

18.



Relation between (I) and (II) (whose configuration in given below is): uhps fn;s x;s ;kSfxd (I) rFkk (II) ds e/; laca/k gS %

(A*) Enantiomers (C) Identical or homomers (A*) izfrcEc:ih (C) le:ih ;k leku

(B) Diastereomers (D) Constitutional isomers (B) foofje:ih (D) lajpukRed leko;oh

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19.

Which of the following is correct for the given compound ?

fn; x;s ;kSfxd ds fy, fuEu esa ls dkSulk lgh gS \

(A) It possesss centre of symmetry (C) It possesss plane of symmetry (A) blesa lefefr dsUnz mifLFkr gSA (C) blesa lefefr ry mifLFkr gSA

(B) It possesss C3 axis of symmetry (D*) Both B and C (B) blesa lefefr C3 v{k mifLFkr gSA (D*) B rFkk C nksuksa

The above pair has relation (A) Enantiomers (B) Diastereomers

(C*) Homologous

20.

mijksDr ;kSfxdks dk ;qXe fuEu esa ls fdl izdkj lEcfU/kr gSa \ (A) izfrfcEc :ih (B) foofje :ih (C*) ltkrh;

(D) Identical

(D) le:i

;kSfxd

DPP No. # 04 (JEE-ADVANCED) Total Marks : 64

Max. Time : 36 min.

Multiple choice objective ('–1' negative marking) Q.1 to Q.6 (4 marks, 2 min.) Comprehension ('–1' negative marking) Q.7 (i to v) (3 marks, 2 min.) Matching List Type (Only One options correct) ('–1' negative marking) Q.8 (3 marks, 2 min.) Single Integer Type Questions Q.9 to Q.10 (3 marks 2 min.) ChemINFO : 4 Questions ('–1' negative marking) Q.11 to Q.14 (4 marks, 2 min.)

[24, 12] [15, 10] [03, 02] [06, 04] [16, 08]

1.

Which of the following statement(s) is/are correct for the above compounds ? (A*) the compound I posses an axis of symmetry. (B) the compound II posses a centre of symmetry. (C*) compound I and II both are optically active and enantiomers of each other. (D*) Diastereomers of both compounds are identical and meso.

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mijksDr ;kSfxdksa ds fy, fuEu esa ls dkSuls dFku lgh gS \ (A*) ;kSfxd I v{k lefefr j[krk gSA (B) ;kSfxd II dsUnz lefefr j[krk gSA (C*) ;kSfxd I rFkk II nksuksa izdkf'kd lfØ; gSa rFkk ,d nwljs ds izfrfcEc:ih gSaA (D*) nksuksa ;kSfxdksa ds foofje leko;oh le:i ,oa ehlks gSA 2.

Which properties of enantiomers are same ? (A*) Boiling Point

(B*) Melting point

(C*) Solubility in water

(D*) µ (refractive index)

fuEu esa ls izfrfcEc:i leko;oh;ksa ds dkSuls xq.k leku gSa \ (A*) DoFkukad (B*) xyukad (C*) ty esa foys;rk 3._

(D*) µ ¼viorZukad½

Which of the following cyclopentane derivatives are optically active ?

buesa ls dkSulk lkbDyksisUVsu O;qRiUu izdkf'kd lfØ; gS \

(A*)

4._

(B*)

(C)

(D*)

Which of the following statement are incorrect ? (A*) Every chiral compound has a diastereomer. (B*) Diastereomers are always optically active. (C) If a compound has an enantiomer, it must be chiral. (D*) Every molecule containing one or more asymmetric carbons is chiral

fuEUk esa ls dkSuls dFku xyr gS ? (A*) izR;sd fdjSy ;kSfxd ,d foofje leko;oh j[krk gSA (B*) foofje leko;oh ges'kk izdkf'kd lfØ; gksrs gSaA (C) ;fn ,d ;kSfxd ,d izfrfcEc:ih j[krk gS] rks ;g fdjSy gksuk pkfg,A (D*) izR;sd v.kq ,d ;k vf/kd vlefer dkcZu j[krk gS] ;g fdjSy gksrk gSA 5.

Which of the following has two-fold axis of symmetry ? (A*) Ethylene

(B*) Cyclopropane

(C*) Cyclobutane

(D*) Benzene

fuEu esa ls dkSu nksgjh&eqM+h gq;h (two-fold) v{k lefefr j[krk gS \ (A*) ,Fkkbyhu (B*) lkbDyksizki s su (C*) lkbDyksC;wVsu C2

Sol.

C2

H

C

H

C2 H

3 C2

(B)

C2 C2

H

H

(C)

H

H C

(A)

H

C2

H

(D*) csUthu

H

C2

H H

H H

C2

H

H

C2

H

H

C2

5 C2 C2

(D)

H C2 C2

3 C2

H

H

H

H C2 C2 C2

C2

7 C2

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6._

Which of the following pair of compounds can be separated by fractional distillation ?

fuEu esa ls ;kSfxdksa dk dkSulk ;qXe izHkkth vklou }kjk i`Fkd gks ldrk gS \

(A)

7.

and rFkk

(B*)

and

(C*)

and rFkk

(D*)

and

rFkk

rFkk

Comprehension Each optically active compound has a characteristic specific rotation. Specific rotation is a number of degrees of rotation caused by a solution of 1 gm of compound per mL of solution in a sample tube 1 dm long at a specific temperature and wavelength. Thus specific rotation can be calculated from the observed rotation using the following formula [ ] T  

 c.

When sodium D line is used,  is indicated by D. S.No. I. II. III. VI.

Name of compound 2-butanol 1-butanol lactic acid -Cholestane

Concentration Specific rotation 1.0 M 1.0 M 0.35 g/mL +160 +240

length of tube 10 cm 10 cm 5.0 cm -

observed rotation +1.030 +2.8 0 -

vuq P Ns n izR;sd izdkf'kd lfØ; ;kSfxd esa ,d vfHkyk{kf.kd fof'k"V ?kw.kZu ik;k tkrk gSA fu;r rki rFkk rjaxnS/;Z ij 1dm yEch ufydk esa 1gm ;kSfxd ds izfr ml foy;u }kjk mRiUu ?kw.kZu dh ek=kk dks fof'k"B ?kw.kZu dgrs gSaA vr% fof'k"B ?kw.kZu dh x.kuk fuEufyf[kr lw=k dh lgk;rk ls izsf{kr ?kw.kZu }kjk dh tk ldrh gSA [ ] T  

 c.

tc lksfM;e D js[kk dk mi;ksx djrs gS] rks dks D }kjk iznf'kZr fd;k tkrk gSA

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Ø-la - ;kSfxd dk uke I. 2-C;wVsukWy II. 1-C;wVsukWy III. ysfDVd vEy VI. -dksysLVsu (i).

fof'k"B ?kw.kZu

1.0 M

-

1.0 M

-

ufydk dh yEckbZ

0

izsf{kr ?kw.kZu 0

10 cm

+1.03

10 cm

-

0.35 g/mL

+16

5.0 cm

+2.8 0

-

+240

-

-

What is the specific rotation of 2-butanol? 2-C;wVsukWy dk (A*) +13.90

(ii).

lkUnz r k

fof'k"B ?kw.kZu D;k gksxk? (B) -13.90

(C) +1.390

(D) -1.390

What is the specific rotation of 1-butanol? 1-C;wVsukWy (A) 1.3

dk fof'k"B ?kw.kZu D;k gksxk?

0

(B*) 00

(C) +13.90

(D) Insufficient Data

vk¡dM+s vi;kZIr

gSA (iii).

What is the observed rotation of a solution of lactic acid when the concentration is double or the length of the tube is doubled-

;fn lkUnzrk nksxquh dj nh tk;s vFkok ufydk dh yEckbZ nksxquh dj nh tk;s rks ySfDVd vEy ds foy;u dk izsf{kr ?kw.kZu D;k gksxk \ Concentration doubled

Length doubled

lkUnzrk nksxquh (A*) (B) (C) (D) (iv).

yEckbZ nksxquh

0

+5.60 +5.60 +2.80 +2.80

+5.6 +2.80 +5.60 +2.80

What is the specific rotation of lactic acid when both the concentration and length of tube is doubled?

;fn lkUnzrk rFkk ufydk dh yEckbZ nksuksa dks nksxquh dj fn;k tk;s rks ySfDVd vEy dk fof'k"B ?kw.kZu D;k gksxk ? (A*) +160 (v).

(B) 320

(C) 640

(D) 00

What is the specific rotation of mirror image of -Cholestane given in table ?

rkfydk esa fn;s x;s -dksysLVsu ds niZ.k izfrfcEc ds fof'k"B ?kw.kZu dk eku D;k gksxk \ (A) +240

(B*) -240

(C) 00

(D) Insufficient Data.¼

vk¡dMs vi;kZIr

gS ½ 8.

Match List I (Compounds) with List II (Relation) and select the correct answer using the code given below the lists :

lwph I (;kSfxd) dks lwph II ¼lEcUèk½ 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

(P)

(1) Identical

(Q)

(2) Enantiomer izfrfcEc

le:i

:i leko;oh

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PAGE NO.- 9

(R)

(3) Diastereomer foofje

(S)

(4) Homologous letkr

Codes

9._ Sol.

:i leko;oh

¼dksM½ : P

Q

R

S

P

Q

R

S

(A)

2

1

3

4

(B*)

3

2

1

4

(C)

4

2

1

3

(D)

3

1

2

4

Total number of plane of symmetry present in CH4. CH4 es mifLFkr ry lefefr dh dqy la[;k gS& 06

10.

Report your answer as XY :

viuk mÙkj XY ds :i esa fyf[k;sA Ans.

22

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PAGE NO.- 10

ChemINFO-1.2

Oxidation

Daily Self-Study Dosage for mastering Chemistry

Anti hydroxylation of Alkenes

Anti hydroxylation of Alkenes Peroxy acid have general structure as

(RCO3H). They are relatively unstable and easily gives na-

scent O hence, acting as oxidant. It converts alkene into epoxides. A combination of RCO 3H followed by hydrolysis [RCO3H(H3O+)] further breaks epoxide to anti hydroxylation product. General Reaction :

Peroxyacid may be any one of these

(a) Note : 1. It is anti addition. Both OH groups add on the opposite side of pi-bond. 2. Double bond of aromatic ring cannot react with these reagents.

= m-CPBA (Metachloro perbenzoic acid)

(b) CH3CO3H = PAA (Peracetic acid) (c) PhCO3H = PBA (Per benzoic acid) (d) CF3CO3H = TFPAA (Trifluoro peracetic acid).

(i) Peroxy acid

Ex.1

     

Ex.2

(ii) H3O 

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

11.

(A*) 12.

(B)

(D) 50% B and 50% C

(C*)

(D)

(C)

(D) None of these

(C) F3CCOOOH/H3O

(D*) All of these

Peroxyacid CH2 = CH2    X , X is -

OH | (A) CH2 — CH2 | OH

(B)

(1) Peroxyacid

   P Product is 

13.

( 2)H3O

(A)

14.

(C)

(B*)

Anti hydroxylation of alkene takes place by (A) m-CPBA/ H3O

(B) CH3 COOOH/H3O

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ChemINFO-1.2

Oxidation

Daily Self-Study Dosage for mastering Chemistry

,Ydhuksa dk ,s.Vh gkbMªksfDlyhdj.k

,Ydhuksa dk ,UVh gkbMªkWfDlyhdj.k (RCO3H) gksrk

ijkWDlh vEy dh lkekU; lajpuk ¼lw=k½

gSA ;g eq[; :i ls vLFkk;h gksrs gS rFkk vklkuh ls uotkr

O ns

nsrs gSA vr% ;g vkWDlhdkjd inkFkZ dh Hkk¡fr dk;Z djrs gSA ;g ,Ydhu dks ,ikWDlkbM esa ifjofrZr dj nsrs gSA RCO3H dk la;kstu blds ckn bldk tyvi?kVu [RCO3H(H3O+)] djus ij ;g vkxs ,ikWDlkbM dks ,UVh gkbMªkWDlhyhdj.k esa rksMrk gSA

lkekU; vfHkfØ;k : bues ls dksbZ Hkh ij vEy gks ldrk gSA (a) Note : 1. ;g ,UVh (anti) ;ksx

= m-CPBA ¼esVkDyksjks

ijcsUtkWbd vEy½

gSA nksuksa OH lewg ikbZ&caèk dh foifjr

fn'kk ls ;ksx djsxsaA (b) CH3CO3H = PAA ( ij,flfVd vEy) 2. ,jksesfVd oy; ds f}cU/k bu vfHkdeZdks ls fØ;k ugh djrs (c) PhCO3H = PBA ¼ijcsUtkWbd vEy½ gS A (d) CF3CO3H = TFPAA (VªkbZ¶yksjks ij,flfVd vEy½ Ex.1



( i) (ii) H3O

Ex.2

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

gS&

(A*)

12.

(B)

CH2 = CH2



OH | (A) CH2 — CH2 | OH

( i)

13.



(ii) H3O

(A)

14.

(C)

(D) 50% B vkSj 50% C

(C*)

(D)

(C)

(D) bues

X , X gS&

(B)

P mRikn

gS&

(B*)

ls dksbZ ughA

buesa ls fdlds }kjk ,Ydhu dk ,UVh gkbMªkWfDlyhdj.k gksxk & (A) m-CPBA/ H3O

(B) CH3 COOOH/H3O

(C) F3CCOOOH/H3O

(D*) mijksDr

lHkh

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