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KVPY PREVIOUS YEAR PAPER (SA STREAM) - CHEMISTRY


(ORGANIC CHEMISTRY)

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02
Organic Chemistry
T
The compound having a triple bond is - 12004
(A)Benzene (B)Cyclohexane (C)Acetylene (D)Glucose

2. Chlorine gas is produced from HCI by the addition of - [2004


(A) K2SO4 (B)KCr (c)KN03 (D) KMnOo

3- When a few drops of concentrated sulphuric acid are added to a few drops of a clear sugar (sucrose)
solution in a test tube, the solution 12004
(A) remains colorless (B) turns black (C) turns blue (D) turns white

4. Thereaction ZnO+ C -----+Zn+CO isanexampleof a 120071


(A) Combination reaction (B) Reduction-ox idation reaction
(C) Displacement reaction (D) Decomposition Reaction

5. The monomer of Teflon is :


120071

(A)-1, (B):. (c) t*s EE


(D)-><-
Me cr
t e p t-F

6. ose yeast , ys
KMnoo -
tud
ln the reaction. Glu , Y the products X and Y, respectively, are tzoo7l
(A) EIOH, CH3COOH (B) MeoH, HCOOH
(c) EtoH, cH3cHo S (D)EIOH, HOCH2CH2OH

7. Penicillin was discovered by: [2008]


(A) Alexander G. Fleming (B)Emil Fisher
(C) Robert B. Woodward (D)van't Hoff

8. Among butane,l-butene,1-butanol and butanal, the compound which is most polar is [20081
(A) butane (B)1-butene (C) 1-butanol (D) butanal

9. Among ethanol, dimethyl ether, methanol, and propanal, the isomers are :
[2008]
(A) ethanol, dimethyl ether, methanol and propanal
(B) ethanol and methanol
(C)ethanol, dimethyl ether, and methanol
(D)ethanol and dimethyl ether

10. Dehydration of 2-pentanol gives :


[2008]
(A)pentane (B) Only 1-pentene
(C) Only 2-pentene (D)A mixture of '1-pentene and 2-pentene

11. Esterification of a compound "X" with molecularformula C3H6O2 with an alcohol "Y" produces a compound
with molecular formula C5H10O2. X and Y respectively, are : [2008]
(A) propanoic acid and methanol (B) propanoic acid and ethanol
(C) acetic acid and ethanol (D) butyric acid and methanol

03
Toprc- wrse KVPY ISTREAM-SA] Questions with Solutions

An aqueous solution of a metal salt (X) reacts with carbon dioxide to give a water soluble compound (Y)
which on heating gives the starting metal salt back. Y when present in water does not produce lather with
soap. The compounds X and Y respectively are [20081
(A)CaCO, and Ca(HCO3)2 (B) Mg (HCO3)2 and MgCO.
(c)Ca(Hcos)z and CaCo, (D) MgCo. and Mg (HCo3)2

13. When calcium carbide is added to water, the gas that is evolved is - [200e]
(A)carbon dioxide (B) hydrogen
(C) acetylene (D) methane

14. The number of possible structural isomers of CrHo is : [20Grl


(A)l (B)2 (c) 3 (D)4

15. Among the four compounds (i) acetone, (ii) propanol, (iii) methyl acetate and (iv) propionic acid, the two that
are tsomenc are - [200e]
(A) methyl acetate and acetone (B) methyl acetate and propanol
(C)propionic acid and methyl acetate
p s
(D) propionic acid and acetone
e
d y st
Reaction of NaCl with conc. H2SO4 liberates a gas X that turns moist blue litmus paper red. When gas X is
passed into a test tube containing egg shell powder suspended in water anothergas, Y is generated which

(A) HCland CO, S tu


when passed through lime water makes it milky. The gases X and Y respectively, ate - -
(B) Cl2 and CO,
[2009]

(C) SO2 and CO2 (D) SO2 and HCI

17. Ethanol on reaction with alkaline KMnOo gives X which when reacted with methanol in the presenee of an
acid gives a sweet smelling compound. Y. X and Y respectively, are - t20091
(A) acetaldehyde and acetone (B) acetic acid and methyl acetate
(C)formic acid and methylformate (D) ethylene and ethyl methyl ether

Saponification is - [2Doe]
(A) hydrolysis of an ester (B) hydrolysis of an amide
(C) hydrolysis of an ether (D) hydrolysis of an acid chloride

ldentify the stereoisomeric pair from the following choices. l20r0l


(A) CH3CH2CHTOH and CH3CH2OCH3 (B) CH3CH2CHTCI and CH3CHCICH3
r

T
(C) CH.-Q=?-a*. and CH,-C=C-CH,

HH H

There are four bottles 1,2,3,4 containing following compounds. [2010]

Bottte-1' NH,;Bottte-2,
O @ "oo,

Bottle-3' Bottte-4
O^cH,; O^(:'
ldentify the bottle :

04
Ongaxrc Cxemsrnv

(l) (A) whose content does not react with 1N HCI or 1N NaOH,
(B) whose content reacts with 1N NaOH only,
(C) whose content reacts with 1N NaOH and 1N HCI both.
(D) whose content reactswith 1N HCI only.
(ll) The bottle whose content is highly soluble in distilled water.

21. ln the following set of aromatic compounds t201f]

(i)
d (ii)o
the conect order of reactivity toward friedel-crafts alkylations is
(iv)

(A)i> ii> iv (B)ii>iv>iii>i


(C) iv > iii>i (D) iii> i> iv > ii

The gas produced from thermal decomposition of (NHo)rCrrO, is : [20ru


(A) oxygen (B) nitric oxide
(C)ammonia (D)'nitrogen

A compound that shows positive iodoform test is


e p
:
s [20rrl

st
(A) 2-pentanone (B) 3-pentanone
(C) 3-pentanol

u d y (D) 1-pentanol

formation of :
St
When chlorine gas is passed through an aqueous solution of KBr, the solution turns orange brown due to the
[201U
(A) KCI (B)HCr (C) HBr (D) Br,

o
I

25.n,onoQ@@thecompoundwhichisnotaromaticis: 120111

(i) (ii) (iii)

(A)i (B) ii (c)iii (D)iv

26. Among the following compounds :


[201r1

H.c1 H"c^
(')
rcH" (ii) H'c^fcH'
cH"cH"
(iv)r."Ucn,
r."X"r. cH.
2, 3 - dimethylhexane is :

(A) i (B) ii (D)iv

05
Toprc- vuse KVPY [STREAM-SA] Questions with Solutions

27 The rnajor product formed in the reaction : [2011]

uo$fffuProductis:
A*^cr
CI CN c

CN I
(i) (iv)

(A)i (c)iii (D)iv

28.
col-lu, is :
e p s
The maximum number of structural isomers possible for the hydrocarbon having the molecular formula
[201U
(A)12 (B) 3

d y st
(c)e (D) 5

S tu
ln the following reaction sequence, X and Y respectively, are :

[201U

(A) H2O2; LiAlHo (B) C6H5COOOH;LiAlH4


(C)C6H'COOOH ; ZnlHg HCI (D) Alkaline KMnO, ; LiAlHo

The major products in the reaction BTTCCHO


N"oH , are : 12014

(A) cHBr.*
o
(B) NaBr.rd"
r
H
./B'
,Ao*" 1r,.

Br Br ar. 7'
(c)NaoBr +A (o) * ,Yo*"
_
,&o, o

31. Among the following substituted pyridines, the most basic compound is : 12014
Me:*'Me

(A)
O

06
32. The major product in the following reaction is :

H3C{=C-H + HBr(excess) 420121

Br H
I /Bt
(A) H.C (B) H.C-C-CH. I
(C) H.C- c-cH, (D) H.C-CH.-CH
I

Br
tl
Br Br
Br

33. The major product in the following at 25"C is: CH.COOH--9!€UIz;-; 120121
(A) CH3CONHCH2CH3 (B) CH.CH=NCH2CH3
(c) NH3+ CH2CH3.CH3COO- (D)CH3CON=CHCH,

Acetylsalicylic acid is a pain killer and is commonly known as :


120121
(A) paracetamol (B)aspirin (C) ibuprofen (D)penicillin

The molecule which does not exhibit strong hydrogen bonding is : 120121
(A) methylamine (B) acetic acid (C) diethyl ether (D) glucose

36. The following two compounds are :


1?0121

H.c&cH'
(A) geometrical isomers
e p s(B) positionalisomers
(C) functional group isomers

d y st (D) optical isomers

37.
S tu
The products X and Y in the following reaction sequerrce are : I2O12l

(A) x, (B)x,

(c)x: (D) X; Y
C

,l
The moelcule having a formylgroup is 120131
(A) acetone (B)acetaldehyde (C) acetic acid (D) acetic anhydride

The structure of cis-3-hexene is [20131

Ft .,/\./ (c),A-.n

07
Toprc- vuse I(VPY IST REAM -SA] Qu estio ns with SoluUms
o
il
The number of sp2 hybridized carbon atoms in g6 = C CH, e-Cn, CH = Qflr, is [20131
- - -
(A) 3 (B) 5 (c) 4 (D) 6

Acetic acid reacts with sodium metal at room temperature to produce [20131
(A)CO2 (B) Hz (c)H2o (D)co

Which of the following is an anhydride ? 120131

o
(o)r."&1"r, 1e1 H.\A (c) H.c\f\*. (D)
H,cl o/cr,
{cH,
,|t. Compound'X'on heating with Zn dust gives compound'Y'which on treatment with Oafollowed by reaction
with Zn dust gives propionaldehyde. The structure of 'X is

e p s
d y st
Stu
2, 3-Dimethylbut-2-ene when reacted with bromine forms a compound which upon heating with alcoholic
KOH produce the following major product. [20131

Br OH
(,)><(")k(ror !,-<-oH
45. The species that exhibits the highest
\ value in a thin layer chromatogram using a nonpolar solvant on a
silica gel olate is 120141

I
tnlo (B)
O
45. The numberof C-C sigma bondsin the compound l2o14l
OO*
(A) 16 (B) 17 (c) 18 (D) 11

The number of isomers which are ethers and having the molecular formula C is lm141
oHroO,

()2 (B) 3 (c)4 (D) 5

The major product of the reaction of 2-butene with alkaline KMnOo solution is 120141

(D)

08
Onanuc Cxemsrnv

49. Among the compounds l-lV the compound having the lowest boiling point is a2o14l

/\..a--- OH
il
IV

(c)ilr (D) rv

50. A compound X formed after heating coke with lime react with water to give Y which on passing over red-
hot iron at 873 produces Z. The compound Z is 120141

(A)o (B)\,1,A, (c)\___/ (D)o


Br
1. Alcoholic KOH 3. HgSO./dl.H,SO., heat
ln the following reaction sequence
,/rn 2. NaNH. 4. Con HNq/H,SO,
;XandYare,
respectiyely 120141

oY
(A) prr: fi""-7to,
"nO

e p s PH

d y st
S tu
NO,

The correct order of acidity of the following compounds is [20151

(A)1>2>3 (B)1>3>2 (c)3>1>2 (D)3>2>1

Reaction of 2-butane with acidic KMnOo gives [201s]


(A)CH3CHO (B) HCOOH (c) cH3cH2oH (D)CH3COOH

54. The gas released when baking soda is mixed with vinegar, is [201sI
(A) CO (B) CO2 (c)cH4 (D)oz ! .o r

09
Toprc- vuse KVPY ISTREAM-SA] Questions wlth Solutlons

The functional group present in a molecule having thq formula C,trOn is


(A)carboxylic acid (B) anhydride (C) aldehyde (D) alcohol

A sweet smelling compounds formed by reacting acetic acid with ethanol in the presence of hydrochloric
acid is [2fiq
(A)CH3COOC2H5 (B)C2H5COOH
(c)c2H5cooH3 (D)CH3OH

57. The maximum number of isomeric ethers with the molecular formula CoHroO is [20151
(A) 2 (B)3 (c)4 (D) 5

58. Reaction of ethanol with conc. Sulphuric acid at 170oC produces a gas which is then treated with bromine
in carbon tetrachloride. The major product obtained in this reaction is : [20151
(A) 1 ,2-dibromoethane (B) ethylene glycol
(D) ethyl sulphate
(C) bromoethane

e p s
The major product of the reaction is

d
:

y st [20151

Stu H?H'zo
> Product

(A) | (c)ilr (D)rv

Among formic acid, acetic acid, propanoic acid and phenol, the strongest acid in water is [20161
(A)formic acid (B) acetic acid
(C) propanoic acid (D) phenol

61. The major product formed when 2-butene is reacted with O, followed by treatment with ZniHrO is [20161
(A)CH3COOH (B)CH3CHO (c)cH3cH2oH (D)CH,=CH,

The IUPAC name for the following compound is [20161

cH3-cH2-cH2-cH2-c-cHz-cHz-c Ho
il
CHz

(A) 2-propylhex-1-ene (B) 2-butylpent-1-ene


(C) 2-propyl-2- butylethene (D) Propyl-1-butylethene

63. The major product formed in the oxidation of acetylene by alkaline KMnOo is [2016]
(A)ethanol (B) acetic acid
(C)formicacid (D)oxalic acid

10
ln the following reactions,X,Y andZare

?" ?*'

O* x-L'Otry*'
(A)X = CH.CI;Y= anhydrousAlClr; Z - HNO3 + HzSO+
(B)X= CH,COCI;Y = anhydrousAlClr; Z = HNO, + HzSOr
(C) X= CH,CI;Y = conc. H2SO4; Z= HNOs + HzSO+
(D)X = CH,CI; Y = dil. HrSOo; Z = HNO,

65. 2,3-dibromobutane can be converted to 2-butyne in two-step reaction using [20161


(A)(i) HCland (ii)NaH (B) (i)alcoholic KOH and (ii) Na NH,
(C) (i)Na and (ii)NaOH (D)(i)Br, and (ii)NaH

e p s
d y st
S tu

11
6.(A) 7. (A)
4.(B) s.(D)
2.(D) 3.(B)
1.(c) 13. (c) r4. (B)
11. (B) 12. (A)
s.(D) 10. (D)
8.(c) 20. (suB) 21. (c)
18. (A) 1e. (c)
16. (A) 17. (B)
1s. (c) (c) 2E. (c)
26. (B) 27.
24. (D) 25. (B)
22.(o) 23. (A) (c)
34. (B) 35.
32. (B) 33. (c)
30. (A) 31. (B)
2e. (B) 42. (A)
40. (A) 4r. (B)
38. (B) 3s. (c)
36. (B) 37. (B)
4E.(D) 4s. (c)
46. (B) 47. (B)
44.(B) 45.(A)
43.(c) s6.(A)
54. (B) 5s. (B)
52. (c) 53.(D)
s0.(A) sl. (B) 63. (D)
62. (A)
57. (B) sE.(A) 5e. (A) 60. (A)

e p s61. (B)

d y st
a triple
tu
Sbond'
L Acetylene (CH = CH) has tO.
oxidise cH3 - cH 4H, - cH, -
"l-'zvl
cFL "T:"1
2. as'
oHl t
+ SClz 2-Pentanol
CH3-CH=CH-CH'?-CH3
2-Pentene (Major)

Concentrated sulphuric acid


is a dehydrating
CH,= g11 - CH' - CH' - CH3
the orsanic compounds like
;;il;Jiiburns
colour of the solution turns
black' 1-Pentene (minofl
Iilr"* so the 11'
+ 11H'O(g)
C,rHrrO,1(s)-@ 12C WatervaPour
Sucrose Carbon H-
(Black) CH3{H,4OOH *
!H,
Prooanotc CH
I

Oxidation
lcid
t-
4. ZnO+C+ /n + CO CH.4H,4OOCH'CH'+ H'O
I Reouaion t EthYlProPanoate

Monorner of Tef lon is Tetafluoroethene(CF'=CF')


12. CaCO.+ H2O + CO2 ----+ Ca(HCO.)'

c.H,P.#-+ zc,HPrr@9r-+ cqcooH o ) CaCO.+ HP+ CO'


Ca(HCO),

Ethanol(C -O-
erent
CH.) have
functional

12
Oncnmc Cxeusrnv

13. CaC, + 2HzO------+ Ca(OH), + CrH, (B) Bottle-2 reacts only with NaOH.
Calcium Water Calcium Ethyne
(C) Bottle4 reactswith both NaOH or HCl.
carbide hydroxide (acetylene)
(D) Bottle-1 reacts with HCI only.
14. CH3-C:CH (Propyne) anO A (cydopropene)
(ll) Bottle-4 is highly soluble in distilled water due
are two possible structural isomers of C.Hn to zwitter ion formation.

15. Propionic acid and mehyl acetate both have same


21. Reativity towards Friedel-Crafts alkylation is
molecularformula (CrHuOr) but different functional
proportionalto electron density in the benzene
groups, so they are isomers.
ring

16. 2NaCl + H2SO4 --------; NarSO4 + 2HCl(g)


(x)
22. (NH4)rCrrO, A, Crro, + Nr+4HrO

2HCl + CaCO, > CaCl ,* HrO + COz


Aldehyde, ketones with acetyl group
(x) (Y)
23.

1 COz o
Ca(OH), ,CaCO.*HrO il
CH3- C -show lodoform test.
lime water (Y) Milky
Suspension
24. Clr+ 211Bl ,2KCl + Br2
reddish brown
17. cH3-cH'-oH -#=cH3cooH
Ethanol

(X)CH3COOH + CH3OH H'


Acetic acid

e p s
25. (i) and (iv) are hetro aromatic and the resonance

Acetic acid Methanol


, CH3COOCH. * HrO

y s
Methyl acetate (Y)
t form of azulene (iii) is aromatic.

18.
S tu d @-ca)
(ii) ls nonaromatic.
CH"-OH
cH"ocoR
t'
CHOCOR + 3NaoH Alkaline , CH_OH
t' 26. Simple nomenclature of alkane.
Hydrolysis
I I
27. The given reaction is S"2 which occurs at sp3 carbon
cH,ocoR cH, - oH
with good leaving group.
(Triester) (Glycerol)
+
28. 9-structural isomers are possible.
3RCOONa
(Soap)
CH3CHTC=CH, CH.{=GCH.
GHr=CH4H=CH, CHr=C=CH{H.

19. "lr"l
CH"-C=C-CH" and CH.-C=C-CH"
HH H
H
I

29.
AAAo
(cis) (trans)
cis and trans are stereoisomeric pair'
t', c"H.coooH ,.. A LiArH, ,. /o'
20. (t) (A) Borfle. o^cH. does not react n -ffi r R.drffi r
with HClorNaOH

13
Toprc- wse KVPY ISTREAM-SA] Questions with Sol utions

It is an example of bromoform reaction (similar 31.


to lodoform reaction).

1' ,o
B'-g-c..
Ar'H
Na*oH-
r. CHBr-r . */ \o-*r'
d +Sn/HCl 1. NaNOJHCI
dBr
31.
CUBr. A

d
H'$+Q.
Me-- -Me Me-- -Me Me--.Me

o 38 (a) cH, - c-cH3


o
il

s
-c-H
(b) cH3
p
y s te o lt

tu d (c) CH. -C-OH


S il
o
The conjugate acid is resonance stabilized. (d) cH3 -c-o-c-cH3
ilil
32. lt is example of electrophilic addition reaction oo
following the markovwrikov rule.
CHs - C- H has formal group.
33. At room temperature, it is a simple acid-base
o
il
reaction resulting in theformation of salt.
o
t5
' \o_, cH3-cH2-NH2
"r,-{(
) NH;cHrCH3.cH3coo-

39.
,MU \,
,/@
U. Acetyl salicylic acid is commonly known as
asprnn.

35. There is not any acidic proton in diethyl ether,


sp sp sp' fl sp' sp' sp'
HC = C CH, C-CH, CH CH, =
hence it does not exhibit strong hydrogen - - sp' -
bonding.
Or
Forl-l{onding in molecule highly electronegative 41. 2CH,COOH + 2Na------+2CH3COONa + H2 t
element & H should be directly connected. ln
(C2H5)2O, H is connected to carbon.
42. -C-O-Q-; an hydride group.
Both A and B differs in position of double bond, illl
oo
hence they are positional isomers.

14
\ .a.3'\d:^.
Br
O cooH cooH cooH
r,o (A) (B) (c)
fo,r.n, (B) OCH3 exerts +M effect destabilizes the
2CH3CH'-CHO conjugate base of the acid.
(C) NO, exerts - M effect and stabilizes the
conjugate base of the acid
Br,lCClo

KMnq / H;
cH, - cH t - cH. 2cH3cooH
",

X
Nonpolar substance will have high Ry value as
il NaHCO.,", + CH3COOHIly

-+ CO21n1 + H2O111 + CHTCOO-(aq1 + N?+1sq1

solvent is nonpolar therefore option (A) will have


high R, value as it have low dipole moment.
e p s
d y st
47. cH3-o-cH2-cH2-cH3
tu
cH3-cH2-o-cH2-cHs

cH.-o-
CH.

cH
I

-cH,
Alkaline A?H
S
55 o
48. KMnq ,"Y
(syn) bH
Oxidation CH: -C-OH+HOCrH,
il

l,ll & lV compound form o


/19. H -bond lll do not form
Fl-€ond

" ,CH, -C-OC2H5 Ethylacetate


50. CaO + C --------+CaC, + CO, il
o
CaC, + H rO -------+ HC = CH + Ca(OH l,
57. C4HloO
= CH3 -CH2 -CH2 -O-CH3
Hot
3Hc:"rRed
Fe n\_/ cHs -cH-o-cH3
CHs

cHs -cHz-o-cH2 -cH3

15
Toprc- ruse l(/PY [ST REAii-SA] Queetlons wlth Solutlons

@ @ @ @ @
CHs -CHz -oH--9glsHre.+ cH;t;cH, CHz- CHz- CHs

Brz
ccrl)cH,-cH,
l' l'
Br Br 2 propyl hex - 1 ene
1,2 - Dibrornoethene
H--o O-H
Alkaline KMNOT
\,/
\./oH CH=CH HC-CH
\o-tt
\J a>
\___/
H4/
Mechanisrn electrophilic addition reaction of HO-C=O (o) H-C=O
alkenes. t- I

H-C=O
60. FormicAcid is StrongestAcid.
e p sH-C=O
Oxalic acid
Acidic strength order :

dy
oH st
Stu
gH.
+I +I
H-C-OH > CH3-C-OH > CH3-CH2-C-OH
illlll
ooo 6 O. cH3cr/Anhv'Arcr3-E1{E
d
Conc. HNOo+ I
+ +l decrease acidic shength (Nitration I
-+ CarboxllicAcid are more acidicThen phenol Conc. HzSOr) I
*x_o"=.1***.1il CHs
I

More Acidic More Stabilize by


O-uo,
Powerful Resonance 65. This is example of Dehydrohalogenation

o-H o@ Br Br Br
o
tt
cH3-cH-cH- cHs
Alcoholic
CH3-CH= C- CH3
I

O*0"-O'
KOH *lBr
+te, lN"NH,
Less Acidic Less Powerful Resonance - I
CH3-C: C-CHg
61. This is example of Reductive Ozorolysis

CHe-CH=CH-CHa
lo'
I
o
"/. ,\' cn.3!!:9
cHa - - 2cH3 -c- H
"1"'i'i, I
o+o !

16

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