ORGANIC CHEMISTRY

TARGET : JEE (Main + Advanced) 2016 DPP

DAILY PRACTICE PROBLEMS

Course : VIJETA (JP) Date : 13-04-2015 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 (3 marks, 2 min.) [60,4 0]

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

g y- ;kSfxd esa C3 rFkk C3/2 lefefr dk v{k mifLFkr gS ysfdu C2 lefefr dk v{k mifLFkr ugha gSA

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
Sol. Easy

(A) (B)

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 (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 gSA

3. Chiral molecules are those which are :

(A) Superimposable on their mirror image
(C) Having no mirror images
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*) Not superimposable on their mirror image
(D) Capable of showing geometrical isomerism
(B*) muds niZ.k izfrfcEc v/;kjksfir ugha gksrs gSa
(D) T;kfefr leko;ork n'kkZus esa l{ke gksA

4. Which of the following has asymmetric carbon atom ?

fuEu esa ls fdlesa vlefer dkcZu ijek.kq gS \

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

5. The structure of (2R, 3R) CH3CH(OH)CH(OH)COOH is -

(2R, 3R) CH3CH(OH)CH(OH)COOH dh lajpuk gS &

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

6. 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) (B*) (C) (D)

7. 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 (D) 3, 3-MkbZesfFkyisUVsu
8. 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 (C) Homologous (D*) Identical

mijksDr ;kSfxdks dk ;qXe fuEu esa ls fdl izdkj lEcfU/kr gSa \

(A) izfrfcEc :ih (B) foofje :ih (C) ltkrh; (D*) le:i ;kSfxd

11. 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 will be

(A) + 45° (B) 0° (C) – 45° (D*) Can not be predicted

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 dk izdkf'kd ?kw.kZu – 45° gS rks dk izdkf'kd ?kw.kZu gksxkA

(A) + 45° (B) 0° (C) – 45° (D*) dqN dgk ugha tk ldrk A

13. 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) (B) (C) (D*)

14. If the optical rotation produced by is +36º, then the optical rotation produced by

will be :

;fn }kjk mRiUu izdkf'kd ?kw.kZu +36º gS rks }kjk mRiUu izdkf'kd ?kw.kZu gksxk&

(A) – 36º (B*) 0º (C) + 36º (D) Unpredictable vKkruh;

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

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

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16. The following two compounds are
fuEu ;qXe ds e/; lEc/k gSA

&

(A*) Enantiomers (B) Diastereomers (C) Identical (D) No relation

(A*) izfrfcEc :i leko;oh (B) foofje leko;oh (C) le:i (D) dksbZ lEc/k ugh

17. Which of the following does not represent D-Lactic acid :

fuEu esa ls dkSulk D-ysfDVd vEy dks ugha n’kkZrk gS

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

Sol. 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 (B) Diastereomers

(C) Identical or homomers (D) Constitutional isomers
(A*) izfrcEc:ih (B) foofje:ih
(C) le:ih ;k leku (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 (B) It possesss C3 axis of symmetry

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

20.

The above pair has relation

(A) Enantiomers (B) Diastereomers (C*) Homologous (D) Identical

mijksDr ;kSfxdks dk ;qXe fuEu esa ls fdl izdkj lEcfU/kr gSa \

(A) izfrfcEc :ih (B) foofje :ih (C*) ltkrh; (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.) [24, 12]
Comprehension ('–1' negative marking) Q.7 (i to v) (3 marks, 2 min.) [15, 10]
Matching List Type (Only One options correct) ('–1' negative marking) Q.8 (3 marks, 2 min.) [03, 02]
Single 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 (4 marks, 2 min.) [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 (D*) µ ¼viorZukad½
3._ Which of the following cyclopentane derivatives are optically active ?
buesa ls dkSulk lkbDyksisUVsu O;qRiUu izdkf'kd lfØ; gS \

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

4._ 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 (D*) csUthu

H
C2 C2
H C2 H
H H
Sol. (A) C C C2 3 C2 (B) 3 C2
H H C2
H C2 H

H H
C2
H H C2
H H C2
H H H H C2 C2
(C) 5 C2 (D) C2 7 C2
C2
C2 C2
H H C2 H H
C2
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) and rFkk

(B*) and rFkk

(C*) and rFkk

(D*) and rFkk

7. Comprehension

Each optically active compound has a characteristic specific rotation. Specific rotation is a number of de-
grees 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. Name of compound Concentration Specific rotation length of tube observed rotation
I. 2-butanol 1.0 M - 10 cm +1.030
II. 1-butanol 1.0 M - 10 cm -
III. lactic acid 0.35 g/mL +160 5.0 cm +2.8 0
VI. -Cholestane - +240 - -

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 lkUnz r k fof'k"B ?kw.kZu ufydk dh yEckbZ izsf{kr ?kw.kZu
0
I. 2-C;wVsukWy 1.0 M - 10 cm +1.03
II. 1-C;wVsukWy 1.0 M - 10 cm -
0
III. ysfDVd vEy 0.35 g/mL +16 5.0 cm +2.8 0
VI. -dksysLVsu - +240 - -
(i). What is the specific rotation of 2-butanol?
2-C;wVsukWy dk fof'k"B ?kw.kZu D;k gksxk?
(A*) +13.90 (B) -13.90 (C) +1.390 (D) -1.390
(ii). What is the specific rotation of 1-butanol?
1-C;wVsukWy dk fof'k"B ?kw.kZu D;k gksxk?
0
(A) 1.3 (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 yEckbZ nksxquh
0
(A*) +5.6 +5.60
(B) +2.80 +5.60
(C) +5.60 +2.80
(D) +2.80 +2.80

(iv). 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 (B) 320 (C) 640 (D) 00
(v). 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 le:i

(Q) (2) Enantiomer izfrfcEc :i leko;oh

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 (R) (3) Diastereomer foofje :i leko;oh

(S) (4) Homologous letkr

Codes 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

9._ Total number of plane of symmetry present in CH4.

CH4 es mifLFkr ry lefefr dh dqy la[;k gS&
Sol. 06

10.

Report your answer as XY :

viuk mÙkj XY ds :i esa fyf[k;sA

Ans. 22

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 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) = m-CPBA (Metachloro perbenzoic acid)

Note :
1. It is anti addition. Both OH groups add on the opposite
(b) CH3CO3H = PAA (Peracetic acid)
side of pi-bond.
2. Double bond of aromatic ring cannot react with these (c) PhCO3H = PBA (Per benzoic acid)
reagents.
(d) CF3CO3H = TFPAA (Trifluoro peracetic acid).

(i) Peroxy acid

Ex.1     

(ii) H3O  Ex.2

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

11.

(A*) (B) (C) (D) 50% B and 50% C

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

OH
|
(A) CH2 — CH2 (B) (C*) (D)
|
OH

(1) Peroxyacid
13.    P Product is

( 2)H3O

(A) (B*) (C) (D) None of these

14. Anti hydroxylation of alkene takes place by

(A) m-CPBA/ H3O (B) CH3 COOOH/H3O (C) F3CCOOOH/H3O (D*) All of these

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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
ijkWDlh vEy dh lkekU; lajpuk ¼lw=k½ (RCO3H) gksrk 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) = m-CPBA ¼esVkDyksjks ijcsUtkWbd vEy½

Note :
1. ;g ,UVh (anti) ;ksx 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

( i)
Ex.1 
(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*) (B) (C) (D) 50% B vkSj 50% C

12. CH2 = CH2  X , X gS&

OH
|
(A) CH2 — CH2 (B) (C*) (D)
|
OH

( i)
13.  P mRikn gS&
(ii) H3O

(A) (B*) (C) (D) bues ls dksbZ ughA

14. 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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