08062024 MEGA Test-01 Ranker’s batch

ORGANIC CHEMISTRY
(for JEE-Mains & Advanced 2025)
Time : 3 : 00 Hr. Max. Marks : 434
=============================================================================================================
SECTION - A [Each Question carry +2 Marks]
300°C
01. The product of reaction CH3CH2OH is :
Cu
(a) C2H6 (b) CH3COCH3 (c) CH3COOH (d) CH3CHO
02. Ethyl alcohol is heated with conc. H2SO4. The product formed is :
(a) H 3C C OC2H 5 (b) C H
2 2
(c) C2H4 (d) C2H6
O
03. Which of the following is soluble in water.
(a) CS2 (b) C2H5OH (c) CCl4 (d) CHCl3
04. Chlorination of toluene in the presence of light and heat followed by treatment with
aqueous NaOH gives :
(a) o-cresol (b) p-cresol (c) 2,4-dihydroxy toluene (d) Benzyl alcohol
05. During dehydration of alcohols to alkenes by heating with conc. H2SO4 the initiation
step is :
(a) Protonation of alcohol molecule (b) Formation of carbocation
(c) Elimination of water (d) Formation of an ester
06. In the following series of chemical reactions, identify Z :
Conc. H 2SO 4 Br2 Excess of
C3H7OH X   Y Z
160-180°C Alco. KOH
(a) CH3 CH CH2 (b) CH3 CH CH2
NH 2 NH2 OH OH
(c) CH3 C CH 2 (d) CH3C  CH
OH
07. Lucas test is used for :
(a) Alcohols (b) Amines (c) Diethyl ether (d) Glacial acetic acid
08. HBr reacts fastest with :
(a) 2-Methylpropan-1-ol (b) 2-Methylpropan-2-ol
(c) Propan-2-ol (d) Propan-1-ol
09. For the reaction,
C2H5OH +HX  ZnCl2
 C2H5X + H2O
the order of reactivity is :
(a) HBr > HI > HCl (b) HI > HCl > HBr (c) HI > HBr > HCl (d) HCl > HBr > HI
10. What is Z in the following sequence of reactions :
PCl5 Alco. KOH (i) Conc. H2SO4
Z  X Y Z
(ii) H2O ; boil
(a) CH3CH2CH2OH (b) CH3CHOHCH3 (c) (CH3CH2)2CHOH (d) CH3CH = CH2
page no # 1
11. Methanol is industrially prepared by :
(a) Oxidation of CH4 by steam at 900°C
(b) Reduction of HCHO using LiAlH4
(c) Reaction HCHO with a solution of NaOH
(d) Reduction of CO using H2 and ZnO-Cr2O3
12. Isopropyl alcohol heated at 300°C with copper catalyst to form :
(a) Acetone (b) Dimethyl ether (c) Acetaldehyde (d) Ethane
13. Which will dehydrate most easily
(a) 3-methyl-2-butanol (b) Ethyl alcohol
(c) 2-methyl propane-2-ol (d) 2-methyl butan-2-ol
14. An organic compound ‘A’ reacts with methyl magnesium iodide, to form an addition
product which on hydrolysis forms the compound ‘B’. Compound ‘B’ gives blue colour
salt in Victor Meyer’s test. The compounds ‘A’ and ‘B’ are respectively :
(a) acetaldehyde and isopropyl alcohol (b) acetone and isopropyl alcohol
(c) acetaldehyde and tertiary butyl alcohol (d) acetaldehyde and ethyl alcohol
15. What is the major product of the following reaction :

O CH3MgI H3 O
 
Et2O
O CH3 OH
O CH3
(a) (b) (c) (d)
CH3 CH3 CH2–OH CH2–CH3
16. In the following sequence of reactions,
P + I2 Mg HCHO H2 O
CH3CH2OH   A B  C   D
ether
the compound ‘D’ is :
(a) butanal (b) n-butyl alcohol (c) n-propyl alcohol (d) propanal
17. Consider the following reaction
C2H5OH + H2SO4  Product
Among the following, which one cannot be formed as a product under any conditions?
(a) Ethyl hydrogen sulphate (b) Ethylene
(c) Acetylene (d) Diethyl ether
18. In the Victor-Meyer’s test, the colour given by 1°, 2° and 3° alcohols are respec-
tively :
(a) Red, blue, violet (b) Colourless, red, blue
(c) Red, colourless, blue (d) Red, blue, colourless
19. The incorrect combination of names for isomeric alcohols with molecular formula
C4H10O is :
(a) tert-butanol and 2-methylpropan-2-ol
(b) tert-butanol and 1, 1-dimethylethan-1-o1
(c) n-butanol and butan1-ol (d) isobutyl alcohol and 2-methylpropan 1-ol

page no # 2
20. A compound ‘X’ with molecular formula CxHyO can be oxidised (not with Fehling So-
lution) to a compound ‘Y’ with the molecular formula C3H6O2 , ‘X’ is most likely to be:
(a) Primary alcohol (b) Secondary alcohol
(c) Aldehyde (d) Ketone
21. Identify Z is the following reaction :

CH3CH2OH PBr X alc. KOH Y (i) H2SO4 , RT

  3
  
(ii) H2O , Heat
(a) CH2 = CH2 (b) CH3CH2OH
(c) CH3OH – O – CH2CH3 (d) CH3CH2 – SO3H
22. The major product in the following reaction :

(i) Hg(OAc) 2 , H2O

?
(ii) NaBH4

(a) (b)
OH O

OH
(c) (d)
OH
23. n-propyl alcohol and isopropyl alcohol can be chemically distinguished by which
reagent :
(a) PCl5 (b) reduction
(c) oxidation with potassium dichromate (d) ozonolysis
24. A compound of the formula C4H10O reacts with sodium and undergoes oxidation to
give a carbonyl compound which does not reduce Tollen’s reagent, the original com
pound is :
(a) Diethyl ether (b) n-Butyl alcohol
(c) Isobutyl alcohol (d) sec-Butyl alcohol
25. When wine is put in air, it becomes sour due to :
(a) bacteria (b) oxidation of C2H5OH to CH3COOH
(c) virus (d) formic acid formation
26. An unknown alcohol is treated with the 'Lucas reagent' to determine whether the
alcohol is primary, secondary or tertiary. Which alcohol reacts fastest and by what
mechanism ?
(a) Secondary alcohol by SN1 (b) Tertiary alcohol by SN1

(c) Secondary alcohol by SN2 (d) Tertiary alcohol by SN2

page no # 3
27.

Consider the above reaction, and choose the correct statement :

(a) The reaction is not possible in acidic medium.
(b) Both compounds A and B are formed equally.
(c) Compound A will be the major product.
(d) Compound B will be the major product.
28. In which of the following pairs the two members can be distinguished by Lucas reagent:
OH
O
(a) CH3CH2CH2OH , CH3— C —CH3 (b) ,
O
OH
(c) , (d) ,
OH OH OH
29. Identify the correct trend of acidic strength for the given alcohols :
OH
(I) OH (II) (III)
OH
(a) (i) > (iii) > (ii) (b) (i) > (ii) > (iii)
(c) (iii) > (i) > (ii) (d) (iii) > (ii) > (i)
30. HBO, oxymercuration-demercuration and acid catalysed hydration will give same
product in :

(a) (b) (c) (d)

31. Mark the correct increasing order of reactivity of the following compounds with
HBr/HCl. (Visualise SN1 reaction)
CH2OH CH2OH
CH2OH

(a) (b) (c)

NO2 Cl
(a) a < b < c (b) b < a < c (c) b < c < a (d) c < b < a
32. Ethylene oxide when treated with Grignard reagent yields :
(a) primary alcohol (b) secondary alcohol
(c) tertiary alcohol (d) cyclopropyl alcohol
33. Which is oxidized most easily ?

(a) CH3 – CHOH – CH3 (b) OH

CH3
(c) CH3 – CH2 – O – CH2 – CH3 (d) OH

page no # 4
 OH
CO2H K2Cr2O 7
34. (P) ; Product (P) is :

O
CO2H
(a) (b) (c) (d)

O
O LiAlH4
35.  x Ac2 O (B)
(A)  
O
x = moles of anhydride consumed
(a) 1 (b) 2 (c) 3 (d) 4

H+/H2 O
36. (A) + CH3MgBr  (B)   Tert-butylalcohol
(A) in the above reaction is ;
(a) CH3CH2COCH3 (b) CH3COCH3 (c) CH3CH2CHO (d) CH3CH2CH2OH

alc. KOH (i) B2H6/THF Cu

37. CH3CH2CH2CH2Br  (A) (B) (C)
(ii) H 2O2/OH – 576 K
The product ‘C’ in the above reaction ;
(a) CH3CH2CH2CH2OH (b) CH3CH2CH2COOH
(c) CH3CH2CH2CHO (d) CH3CH2CH = CH2

(i) NaOH (i) CHCl3

38. Cl2 ,FeCl3
C6H6  (A) (B) (B) dil. HCl (D)
(ii) 623 K, 200atm (ii) NaOH

The major product ‘D’ in the above sequence of reaction is :

ONa OH CH3 OH
CHO CHO CHO COOH
(a) (b) (c) (d)

39. The increasing order of the boiling points for the following compounds is :
(I) C2H5OH (II) C2H5Cl (III) C2H5CH3 (IV) C2H5OCH3
(a) (IV) < (III) < (I) < (II) (b) (III) < (II) < (I) < (IV)
(c) (III) < (IV) < (II) < (I) (d) (II) < (III) < (IV) < (I)
40. Which of the following reaction conditions are used for the conversion of ethanol to
ethylene.
(a) conc. H2SO4 / 70°C (b) dil. H2SO4 /140°C
(c) dil. H2SO4 /100°C (d) conc. H2SO4/170°C
41. If the boiling point of ethanol (molecular weitht = 46) is 78°C , the boiling point of
diethyl ether (molecular weight = 74) is :
(a) 100°C (b) 78°C (c) 86°C (d) 34°C
42. Which one of the following alcohols is expected to have the lowest PKa value ?
(a) Ethanol (b) 2-Fluoro ethanol
(c) 2,2,2-Trifluoroethanol (d) 2-Chloroethanol

page no # 5
43. Which one of the following alcohol contains CSp2 – OH bond ?
(a) vinyl alcohol (b) allyl alcohol (c) benzyl alcohol (d) carbolic acid
44. (CH3)3 C – OH 
H2 SO 4
(CH3)2C = CH2 ;
This reaction takes place through :
(a) SN1 mechanism (b) SN2 mechanism (c) E1 mechanism (d) E2 mechanism
45. An alcohol (A) on heating with concentrated H2SO4 gives alkene (B) which can show
the geometrical isomerism. The compound(A) is :
(a) (CH3)2 C(OH) CH (CH3)2 (b) (CH3)2 C(OH) CH2Me
(c) CH3 CH2 CH(OH) CH3 (d) All of these
46. The relative rates of reaction with concentrated H2SO4 of the following is :
OH OH
(I) OH (II) (III)

(a) I > II > III (b) II > I > III (c) I > III > II (d) II > III > I

47. (A) 1–Methylcyclohexanol. Here (A) is :

(a) (b) (c) (d) (a) & (b)

48.

Select schemes A, B, C out of

(I) Acid catalysed hydration (II) HBO (III) Oxymercuration-demercuration
(a) I in all cases (b) I, II, III (c) II, III, I (d) III, I, II

49. RMgX (A) (B) , (B) will be :

(a) 1° ROH (b) 2° ROH (c) 3° ROH (d) Alkene

50. Which of the following order is incorrect ?
(a) CH3 – CH2 – OH > CH3 – CH2 – CH2 – OH > CH3 – CH2 – CH2 – CH2 – OH
(Solubility in H2O)
(b) CH3 – CH2 – OH > CH3 – O – CH3 > CH3 – CH2 – CH3 (Boiling point)
(c) Pentan-1- ol > Pentanal > Ethoxy ethane (Boiling point)
(d) CH3 – OH > CH3 – CH2 – OH > CH3 – CH2 – CH2 – OH (Boiling point)

page no # 6
51. What would be the major product of following reactions :

(a) (b)

(c) (d)

CHO Zn-Hg
52. HO CH2 Product is :
Conc. HCl

(a) ClCH2 CH3 (b) CH3 CH2Cl

(c) HO CH2 CH3 (d) ClCH2 CH2Cl

53. The catalyst involved in Tischenko reaction of Butanal is (A) and the product
obtained in Perkin reaction of p-Tolualdehyde is (B). (A) and (B) are :
(a) Aluminium Ethoxide ,-Keto ester (b) Potassium Cyanide ,-hydroxy ketone
(c) Potassium Cyanide ,-unsaturated acid
(d) Aluminium Ethoxide , -unsaturated acid

C 6 H5
54. Base (P)
O

Cl

The major product (P) in above reaction will be :

C 6 H5 C 6 H5
C 6 H5 C 6 H5
(a) O (b) (c) (d) OH
O
O OH
OH
55. The product formed by the reaction of ethyl acetate with sodium ethoxide is :
(a) Ethyl acetoacetate (b) Ethyl propionate
(c) Propane-2 , 3-dione (d) 3-Oxobutanal

56.

The reagent (X) in the above reaction is :

(a) BrCH2CH2COOH (b) (CH3CO)2O (c) (CH3CH2CO)2O (d) (CH3CH2COO)2

page no # 7
57. The structure of first intermediate formed in the mechanism of the reaction

_
O OH
 is :

O O O

(a) (b) (c) (d)

O
58. Most reactive towards nucleophilic addition is :
O O
(a) CF3—— C ——CF3 (b) CH3—— C ——CH3

O
(c) —— C —— (d) —— C ——
O Me Me
59. What is the major product obtained from the following reaction ?
CN
+
i)
H3O ii) heat

O
COOH COOH CH2 —OH
(a) (b) (c) (d)
OH O O
O
O

60. on treatment with Zn—Hg/ conc. HCl gives :

COOH

(a) (b)
COOH

OH OH

(c) (d)
OH

61. In the given transformation which of the following is the most appropriate reagent:
CH = CHCOCH3 CH = CHCH2 CH3
Reagent
 

HO HO
_
(a) NH2 NH2 , OH (b) Zn—Hg/ HCl (c) Na, Liq. NH3 (d) Na BH4

62. The intermediate formed in aldol reaction is :

(a) carbocation whose +ve charge is stabilised by resonance .
(b) carbocation whose +ve charge is not stabilised by resonance .
(c) carbanion whose —ve charge is stabilised by resonance .
(d) carbanion whose —ve charge is not stabilised by resonance .
page no # 8
SECTION - B [Each Question carry +4 Marks]
63. The correct statement about the synthesis of erythritol C(CH2OH)4 used in the prepa-
ration of PETN is :
(a) The synthesis requires four aldol condensations between methanal and ethanal.
(b) The synthesis requires two aldol condensations and two Cannizzaro reactions.
(c) The synthesis requires three aldol condensations and one Cannizzaro reaction.
(d) Alpha hydrogens of ethanal and methanal are involved in this reaction.
64. 1-propanol and 2-propanol can be best distinguished by :
(a) oxidation with alkaline KMnO4 followed by reaction with Fehling solution.
(b) oxidation with acidic dichromate followed by reaction with Fehling solution.
(c) oxidation by heating with copper followed by reaction with Fehling solution.
(d) oxidation with concentrated H2SO4 followed by reaction with Fehling solution.
65. (I) 1, 2-dihydroxy benzene (II) 1, 3-dihydroxy benzene
(III) 1, 4-dihydroxy benzene (IV) Hydroxy benzene
The increasing order of boiling points of above mentioned alcohols is :
(a) I < II < III < IV (b) I < II < IV < III
(c) IV < I < II < III (d) IV < II < I < III

66. Reaction of Grignard reagent, C2H5MgBr with C8H8O followed by hydrolysis gives
compound "A" which reacts instantly with Lucas reagent to give compound B,
C 10 H 13 Cl. The Compound B is :

(a) (b) (c) (d)

67.

Consider the above reaction and identify the Product P :

(a) (b) (c) (d)

page no # 9
68. Which of the following oxidation reactions is incorrect ?

( a) (No CH3COOH will be produced)

(b)

(c)

(d)

69. Among the following ethers, which will produce methyl alcohol on treatment with
hot concentrated HI ?
CH3
(P) CH3 – C – O – CH3 (Q) CH3 – CH – CH2 – O – CH3
CH3 CH3
(R) CH3 – O – CH3 (S) CH3 – CH2 – CH – O – CH3
CH3
(a) P , Q (b) Q , R (c) Q , S (d) P , R
70. Arrange the following compounds in increasing order of boiling point.
Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol.
(a) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
(b) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(c) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(d) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol
71. Match the compounds given in List I with their characteristic given in List II.
List-I List-II
(A) CH3(CH2)3NH 2 (i) Alkaline hydrolysis
(B) CH3C  CH (ii) With KOH (alc.) and CHCl3 produces bad smell
(C) CH3CH2COOCH3 (iii) Give white ppt. with ammoniacal AgNO3
(D) CH3CH(OH)CH3 (iv) With Lucas reagent cloudiness appears after
5 minutes
(a) A – (ii), B – (i), C – (iv), D – (iii) (b) A – (iii), B – (ii), C – (i), D – (iv)
(c) A – (ii), B (iii), C – (i), D – (iv) (d) A – (iv), B – (ii), C – (iii), D – (i)
72. In solvolysis of 1, 2-dimethyl propyl p-toluene sulfonate in acetic acid at 75ºC, (alk-
ene + substitution products) will be formed by mechanism ?
(a) SN2 , E2 (b) SN2 , E1
(c) SN1 , E2 (d) SN1 , E1
page no # 10
73. Statement-I : Ethyl pent–4–yn–oate on reaction with CH3MgBr gives a 3° alcohol.
Statement-II : In this reaction, one mole of ethyl pent–4–yn–oate utilizes two moles
of CH3MgBr .
Choose the most appropriate answer from the options given below.
(a) Both statement I and statement II are false.
(b) Statement I is false but statement II is true.
(c) Statement I is true but statement II is false.
(d) Both statement I and statement II are true.

74.

Identify (X) :

(a) (b)

(c) (d)

75.

which is true about alcohol/ketone and Reagent ?

List-I (Alcohol/Ketone) List-II (Reagent)

(a) (A)P ; (B)R ; (C)S ; (D)Q (b) (A)R ; (B)P ; (C)Q ; (D)S
(c) (A)S ; (B)R ; (C)P ; (D)Q (d) (A)S ; (B)Q ; (C)R ; (D)P

page no # 11
76. Find the major product of following reaction :

(a) (b)

(c) (d)

77. An ester (A) (CnH2nO2) on reaction with excess amount of a Grignard Reagent (B)
(CmH2m+1MgBr) followed by hydrolysis gives :

OH OH
CH3(CH2)4C CH3(CH2)3C
(a) + EtOH (b) + CH3(CH2)3OH
Me Me Me Et
Et Me OH
(c) CHOH + CH3CH2CH2OH (d) Et 2C +
Me OH

dil. NaOH CHO

78. 2(A)  
CH
OH
NaOH
(A) + HCHO (excess)  Product is :
OH OH OH OH
OH
(a) (b)
CH(OH)CH 2CHO
OH (c) (d)
HO CH2OH
OH OH OH
79. Adipic acid on heating followed by reaction with m-CPBA gives :
(a) six memebered homocyclic ester (b) five memebered hetrocyclic ester
(c) six memebered homocyclic acid (d) five memebered hetrocyclic acid
80. Select reaction which does not involve formation of free radical.
(a) Hunsdicker reaction (b) Wurtz reaction
(c) Williamson’s ether synthesis (d) Kolbe’s electrolysis synthesis
81. Which of the following will not produce methane with MeMgBr ?
O O
(a) Ph – C – CH2 – C – Ph (b) Me – C  C – H (c) H2O (d)

page no # 12
82. CH3 – CH3  CH4
Identify reagent sequence for above conversion :
(a) (i) Cl2 /hv ; (ii) Na/Et2O
(b) (i) Cl2 /hv ; (ii) Aqueous KOH ; (iii) PCC (iv) Red P/HI
(c) (i) Cl2 /hv ; (ii) Aq. KOH ; (iii) KMnO4 , NaOH/ (iv) NaOH/CaO/
(d) (i) Br2 /hv ; (ii) Alc. KOH/ ; (iii) O3 , Zn (iv) H2 , Pd
O
83.
COOH 
X NaBH4 Y
H+ Z
COOH gas 
Consider the following statements for above reaction sequence ?
(P) ‘Z’ product is sweet smelling substance.

HO

(Q) Reaction of ‘X’ OH OH H+ LAH H+ O hemi ketal product.

(R) ‘Y’ product librate CO2 gas with aqueous NaHCO3 and soluble in aqueous NaOH
(S) ‘Z’ product is resolvable.
Which are correct :
(a) P , R (b) Q , R (c) P , S (d) P , Q , R , S
Passage for Q. No 84 & 85
An optically active alkene (P) on reaction with H2 , Pt produces optically inactive
(Q). (P) on reaction with 1 % KMnO4 followed by HIO4 Produces (R) & (S). When
(R) & (S) are reacted in 1 : 2 ratio with NaOH, , it produces (T) & HCOONa.
84. Consider the following alkenes.

(I) (II) (III) (IV)

Which of the following can’t possible as (P) ?

(a) I , II (b) II, III, IV (c) I, III, IV (d) I , II
85. (T) on reaction with HCHO in acidic medium produces :
O
O O O
(a) (b) Ph O (c) (d)
O O O Ph

page no # 13
 dil. NaOH
86. (A)  
OH
O
(i) I2/NaOH
(A) (B)
(ii) H+
(iii) Heat
Which of the following is correct :
(a) (A) contains two chiral carbons
(b) (B) on reaction with LiAlH4 gives Cycloheptanol
(c) (B) on reaction with peracid gives seven memeberd heterocyclic ester.
(d) (A) on reaction with excess Ph3P = CH2 gives conjugated diene.
NaOH
87. Ethanal + HCHO (excess)  (A) + HCOONa

Propanal + HCHO (excess)  NaOH (B) + HCOONa

The mixture of 2 mol of (A) and 3 mol of (B) on reaction with excess amount of CH3MgCl
gives ‘n’ moles of CH4 gas.
CHO
aqueous
Product (P)
ethanolic KCN

The degree of unsaturation (DU or DBE) of (P) is :

1 1 1 1
(a) (2n – 1) (b) (2n + 1) (c) (2n + 3) (d) (3n – 1)
3 3 5 5
O O
(i) aq. NaOH
88. Br C C CH2Cl Product is :
(ii) MeI
OH OMe OH

(a) Br CH C CH2OH (b) HO C CH2OH

OMe COOMe
OH OH

(c) Br C CH2OH (d) Br C CH2Me

COOMe COONa

Me O
Zn - Hg
89. Product is :
Conc. HCl

Me
Me Me Me Cl

(a) Cl (b) Cl (c) (d) Cl

Ph Ph Ph
Cl

page no # 14
 O
(i) NH2NH 2(excess)
90. Product is :
(ii) OH , 

N–N

(a) (b)

NH2

(c) (d)
NH 2

91. Which of the following is Incorrect for benzaldehyde :

(a) It reduces Tollen reagent into Ag and when it is reduced by Zn-Hg/Conc. HCl
Toluene is obtained.
(b) It on reaction with ethanoic anhydride in presence of sodium acetate gives
Crotonic acid.
(c) It on cross Cannizzaro reaction with methanal gives Benzylalcohol and when it is
reduced by LiAlH4 benzyl alcohol is obtained.
(d) In presence of aq. ethanolic KCN it gives racemic mixture of -hydroxy ketone and
on Perkin reaction it gives ,-unsaturated acid.
92. In the following structure the number of HemiAcetal (HA) and Ketal (K) groups are x1
and x2 respectively :
O O
O
OH OH O
O

O
HO O
O O O O
HO O
The difference in number of acyclic and cyclic isomers of C5H10 is :
(a) x1 – x2 (b) x1 + x2 (c) 2x1 – x2 (d) 3x1 – 2x2
93. Which of the following product can be obtained by Perkin reaction :
CH2 COOH
(a) Me—— ——CH = CH——CH = O (b) ——CH2 CH = C

COOH COO Et
(c) ——CH = C (d) ——CH = C
Me
NO2 NO2

page no # 15
 — +
O EtO Na
94. Product is :
O
Et
O
O
O OEt OH
(a) (b) (c) O O (d)
O O
O OH
EtO
C
O
O
95. When the compound
HOOC COOH
HOOC COOH
HOOC
O COOH

HOOC COOH
is heated, ‘n’ moles of CO2 and ‘m’ moles of H2O is eliminated. The number of sp2 c’s
in the product are :
(a) n2 + m3 (b) n3 – m2 (c) m n2 (d) n m2

96. Phosphorousylide (A) + Carbonyl compound (B)

Me2C = CH CH = CHMe + Ph3P = O
(B) is formed by condensation reaction between two carbonyl compounds (C) and
(D) using NaOH then heat. (D) but not (C) can reduce Fehling solution.
Which of the following is Incorrect .
(a) The number of ‘H’ atoms in (A) are equal to 19
(b) (C) on reaction with PhMgBr gives racemic mixture
(c) (D) on reduction with NaBD4 followed by H2O gives racemic mixture
(d) (D) on reaction with Al(OEt)3 gives ethylacetate.
97. In which of the following intramolecular aldol condensation reaction more than two
products are possible (Don’t consider stereoisomerism) :
O
CHO

(P) CHO (Q)

(R) (S)

O
(a) P , R (b) Q, R, S (c) P, Q (d) P, S
page no # 16
98. The rate of reduction of the following carbonyl compounds by NaBH4 :

O O

CH3

(a) (b) (c) (d)

99. Methyl acetate on treatment with excess of C2H5MgBr produces :

(a) CH3— OH (b) CH3— OH (c) C2H5— OH (d) CH3— OH

_ _
100. CH3 CH2 CHO  (A) ;
OH CH3 COO C2H5 C
2H5
O
 (B)
(A) and (B) are :
(a) —hydroxy aldehyde , —keto ester (c) Acetal , —keto ester
(c) —hydroxy aldehyde , —keto ester (d) Acetal , ketal
101. Est er ( A) + Gr ign ar d r eagen t ( B) ( ex cess) , f ollow ed by h ydr olysis  1O alcohol
(C) + 3O alcohol (D)
(C) can not perform haloform reaction
(A) and (D) are :

(a) CH3 — C , CH3 — CH3 (b) CH3CH2—C , Et CMe2OH

(c) H—C , Me3C — OH

(d)CH3CH2CH2—C , (CH3CH2CH2)3C—OH .

102. Which of the following is not an intermediate in the acid-catalysed reaction of ben
zaldehyde with 2 equivalents of methanol to give benzaldehyde dimethyl acetal ?

(a) (b) (c) (d)

page no # 17
 OH
N

103. Me conc.
 H2SO4
 Product is :

N
OH
O
NH O
NH
(a) (b)

Me
NH
NH——C—— ——Me
O
O
NH O
NH O

(c) O (d)

NH——C—— ——Me NH——C—— ——Me

O

104.

B is :

(a) (b) (c) (d)

105. The benzoin condensation of p—tolualdehyde gives a product which contains :

(a) three sp3 C’ s and one sp2 C (b) two sp3 C’ s and thirteen sp2 C’ s
(c) three sp3 C’ s and twelve sp2 C’ s (d) three sp3 C’ s and thirteen sp2 C’ s
106. The appropriate reagent for the following transformation is
1—acetyl—3—hydroxy cyclopentane  3—ethyl cyclopentanol—1
_
(a) Zn(Hg), HCl * ( b) NH 2NH2, OH (c) H2/ Ni (d) NaBH4

107. Chloral NaOH

 Product is :
(a) CH Cl3 + HCOONa (b) CCl3 COONa + CHCl3
(c) CHCl3 + CH3 COONa (d) CH3 Cl + CCl3 COONa

page no # 18
 NH2
N
_ +
108. i)
OH , heat ii) H
 Product is :

O=CH CH=O

(a) (b) (c) (d)

O O
O O O O
O O
109. Chiral ‘C’ is generated in :
O O

(a) i)
Mg—Hg ii) H2O
 (b) i)
N2H4 ii) KOH, heat

O O

(c) Zn—Hg/
 Conc. HCl
 (d) NH
2OH


O
+
110. i)
NaOH ii) H
 Product is :
O
OH
OH
(a) (b)
COOH OH

O
(c) CH2 (d)
C O O
O
O O
111. Ph—MgBr (1mole) + (CH3)2 CH— C —Cl  [X] Zn—Hg/
 HCl
 [Y]

Identify the structure of [Y] .

(a) Ph— CH— CH2—CH3 (b) Ph—CH2— CH —CH3
CH3 Me
CH3
(c) Ph— C CH3 (d) CH2—CH2—CH3
CH3 CH3

page no # 19
 _
112. O CHO OH
 (A) , (A) is :

CHO CHO

_
O CH2 OH O COO
(a) +
COO _ CH2 OH COO _ CH2 OH

_
O CH2 OH O COO
(b) +
COO _
CH OH CH2 OH
2 C OO _

O CHO O CHO
(c) (d)
COO _ CH2 OH O
O
CH2 Cl

113. aq.
 NaOH
 Product is :
Br CHO

O O

OH OH

OH
Br
HO COONa
(a) (b)

O O
CH=O

Cl Cl Cl

OH HO CHO
HO HO COONa
(c) + (d)

O O
CH=O CH=O

page no # 20
 +
114. i)
Mg, ether ii) Methyl ethanote, then H3O

(excess)

HO
OH
OH
(a) (b) (c) (d)
HO
CH3

Integer Type #
115. 0.092g of a compound with the molecular formula C3H8O3 on reaction with an ex-
cess of CH3MgI gives 67.2 mL of methane at STP. The number of active hydrogen
atoms present in molecule of the compound is ?
116. An unknown compound (A) (molar mass = 180) on acetylation gives a product (mo-
lar mass = 390) then find the number of hydroxyl group present in compound (A) ?

OCH3
OCH3
117. How many moles of ‘HI’ will react with
OCH3
118. Find out number of alcohols that can give positive iodoform test.
OH OH
OH
(a) (b) (c) CH–CH3 (d)
OH

OH HO

(e) CH3 – CH2 – OH (f) CH2–OH (g) (h)

H2SO 4
119. x

x = number of alcohol including stereo isomers.
Find x :
120. How many primary alcohols (including stereoisomers) are possible with formula
C5 H12 O ?
121. How many of the following will give silver mirror with tollen’s reagent ?
OH
O
(i) Ph – CH = O (ii) HCHO (iii) (iv) Me—CCH

OH

(v) HCOOH (vi) MeCOOH (vii) O (viii) HCCH

OH
OEt
Me – CH – C – Me
(ix) (x) Me – CH2 – CH
O OH
page no # 21
122. Total number of compounds whose molecular mass is increased by 126 gm on reac-
t ion w it h ex cess CH 3COCl/Pyridine :

(i) (ii) (iii) (iv)

(v) (vi) (vii)

(viii) (xi) (x)

123. Consider all possible carbonyl compounds including stereoisomerism of molecular

formula C5H10O , All these isomers are independently reacted with NaCN / HCN
(Notes : stereoisomers are also reacted separately). The total number of carbonyl
compounds that give a racemic mixture is ..... .
124. Total number of moles of CO2 evolved in following reaction per mole of compound
‘M’ is ?

KMnO 4
(M)


125. Phosphorous ylide (A) + Ketone (B) Ph3P = O +

CaOCl2
(B)  heat
   (C)
The sum of no. of sp3 carbon atoms in (A) and (C) is :
O
126. HO O C O OH (1 mol)

reacts with 13 mol of phenyl magnesiumbromide. ‘n1’ moles of hydrocarbon is ob

tained and ‘n2’ moles of Grignard reagent remain unreacted. The value of n1 +2n2 is:

page no # 22
 O
HOOC COOH
HOOC COOH

127. on heating produces ‘n1’ moles of CO2 and ‘n2’ moles of H2O.
O COOH

COOH
The product obtained has DU = n3 . The value of n1 + 2n2 + 3n3 is :

128.

The no. of moles of CH3 MgX consumed by the 1 mol of reactant are.

O
14 O
OH
O

12
129. HO on heating undergoes a decreases in MW of .

O O 14

O OH

O COOH
130. on heating undergo a decrease in no. of sp2
HOOC O
hybridised carbons by x% . The value of ‘x’ is :
131. Consider of the following possible combination to prepare 1–phenyl–1, 3–butadi
ene from Wittig reaction ?

CH3
(1) + Ph3P = CH–CH=CH2 (2) + O=C
COCH3 CH=CH2
C = PPh3
H

H
(3) + Ph3P = CH–CH =CH2 (4) +O=C
CHO
C = PPh3 CH=CH2
H
How many are correct :

page no # 23