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O O
O O
(C) (D)
O
3.
A CH 3Li D
CH 3CH 2CH 2Br B C
CHEMISTRYWORLD.IN-1
(A) A: ROH/KOH D: Cyclopentanone (B) A: PPh3 D: Cyclopentanone
(C) A: CuI D: Cyclopentanone (D) A: Cyclopentanone D: PPh3
1.CH3Li 2.H2O
4. Cis-crotonaldehyde ( CH3CH=CHCHO) A+B
If only 1,2-addition is considered, what is the relation between A & B ?
(A) diastereomers (B) enantiomers
(C) constitutional isomers (D) none
5. HIO4 HIO4
HOCH 2CH 2 OH A CH3CHOHCHOHCH 3 B
HIO4
Pinacol C
6. MnO2
CH 2 =CHCH 2OH A
PPh3 NaH B
CH 3CH=CHCH 2 Br
A+B
C
C is
(A) CH 2 =CH-CH=CH-CH=CH-CH 3 (B) CH 2 =CH-CH=CH-CH=CH 2
(C) CH 2 =CH-CH 2 -CH=C=CH-CH 3 (D) None
7. Which pair of following compounds could serve as the reagents X and Y respectively
for the following conversion
PPh3 NaH
Y (CH ) CHCH=C(CH )CH CH
X 3 2 3 2 3
1.(CH3 ) 2CHCH 2 Br 2.(CH 3 ) 2 CHBr 3.CH 3CH 2CH(Br)CH 3 4.(CH3 )2 CHCHO 5.(CH 3 ) 2CO
(A) 1 & 5 (B) 3 & 4 (C) 2 & 5 (D) 2 & 4
CHEMISTRYWORLD.IN-2
(A) 1.OsO4/H2O ; NaHSO3 2. HIO4 (B)1.O3; Zn/H+ 2. OH-/
(C) RCO3H/H+ (D) O3 ; H2O2
10. When the vapour of liquid X is passed over hot Cu, a reaction occurs and the product
gives an orange color with Fehlings solution. X could be
(A) propan-1-ol (B) propan-2-ol (C) propanal (D) propanone
11. A conversion of 2,5-dimethylfuran into 2,5-dimethylpyrrole (see equation) may be
accomplished in two steps.
i) hydrolysis of the furan in aqueous acid; ii) heating the hydrolysis product with
excess ammonium carbonate
What is the intermediate hydrolysis product used in the second step?
O N
(A) 2,5-hexanedione (B) 3,4-hexanedione
(C) hexanedial (D) 2,5-dimethylcyclopentanone
12. Select the best reagent combination for the following conversion.
13. Select the correct order of equilibrium constants for the hydrate formation in the
following compounds.
O O O
CHO
O2N H2N
I II IV
NO2 III
(A) II > III > I > IV (B) III > II > I > IV (C) I > II > III > IV (D) I > II > IV > III
14. Select the best sequence of reagents for the following conversion.
OH OH
OH OH
OH O
(A) 1. HCHO/dryHCl 2. KMnO4 3. Dil.HCl
CHEMISTRYWORLD.IN-3
(B) 1. (CH3)2O/dryHCl 2. KMnO4 3. Dil.HCl
(C) 1. CH3CHO/dryHCl 2. KMnO4 3. Dil.HCl
(D) 1. PhCHO/dryHCl 2. KMnO4 3. Dil.HCl
15.
OH
Dil.H+
18.
OH OH
TsOH
CH3-CH-CH2-CH-CH3 + HCHO Major product is
Meso
(A) (B)
O O O O
(C) Both A and B in equal amounts (D) None of the above
19.
CHEMISTRYWORLD.IN-4
O
Dil.HCl
A + B (B gives positive Tollen's test)
O
K2Cr2O7 C is
A C
20.
O
(NH4)2CO3 Major product is
O
(A) (B) (C) (D)
N N
N N
21.
CH2Br
1.ex PPh3 glyoxal
Major product is
2.ex. NaH
CH2Br
O
O
CHO
(A) (B)
CHEMISTRYWORLD.IN-5
CHO & CHO
&
CHO
CHO
(C) (D)
&
CHO &
CHO CHO
O OH- O
(A) O O (B) O O
(C) O (D) O
H
O O
25.
CH3COCl OH- 1.CH3MgBr H+ 1.O3
A B + C D A+E+F
AlCl3 2. H 2.Zn/H+
E and F can be
NH2
(A) (B) N (D) N
N (C)
N
SECTION-II Multicorrect
27. Pentaerythritol, C(CH2OH)4, used in making explosives, can be obtained by treating
(A) excess acetaldehyde with H+
(B) acetaldehyde and excess formaldehyde in basic medium
(C) treating acetaldehyde with 3 mols of formaldehyde in the presence of base and
then treating the product with LiAlH4.
D) excess formaldehyde with OH-
CHEMISTRYWORLD.IN-6
28. Vinyl alkyl ethers, RCH=CHOR1, are very rapidly hydrolysed by dilute aqueous acid to
form the alcohol R1OH and the aldehyde RCH2CHO. Hydrolysis in H2O18 gives alcohol
R1OH containing only ordinary oxygen. Select the correct statement(s).
(A) cleavage occurs through hemiacetal formation
(B) after the cleavage the aldehyde may contain O18
(C) cleavage occurs through acetal formation
(D) if the hydrolysis is carried out in D+/D2O, the resultant aldehyde may have
deuterium attached to carbon.
29. Benzaldehyde can be prepared from benzoic acid in which of the following ways.
(A) i. NaBH4 ii. H2O (B) i. LiAlH4; H+ ii. PCC
(C) i. SOCl2 ii. DIBALH/H2O (D) i. ROH/H+ ii. DIBALH/H2O
NO2
33.
dil. H+
CH3-CH=CH-O-CH2-CH3 A+B
If A gives positive haloform test, select the correct statement(s) about B.
(A) It gives positive Fehlings test. (B) It reduces Ag+ to Ag.
(C) It gives off H2 with Na. (D) It decolorises Br2/H2O
CHEMISTRYWORLD.IN-7
34.
OH
O
and
O can be distinguished by
O
(A) Na (B) Lucas test (C) [Ag(NH3)2]+ (D) Fehlings solution
36.
1.cold KMnO4
A 2.HIO4 B+C
If both B and C respond positively to iodoform test, A can be
37.
1.(CH3)2CuLi 1.LiAlH4
C CH3CH=CHCHO A
2.H2O (cis) 2.H2O
1.CH3Li
2.H2O
B
Select the correct statement(s).
(A) A is a mixture of diastereomers (B) B is a mixture of diastereomers
(C) A is a pure compound (D) C is a pure compound
38. Which of the following undergo(es) racemisation when dissolved in basic solution?
(R) (R)
(R)
(R)
CHEMISTRYWORLD.IN-8
H H H
40
NH2OH A+ B
HCl
H+/ H+/
C D
If C is more basic than D, select the correct structural formulae for C and D.
O O
(A) (B) (C) (D)
N O O
N
N N
C C D
D
41.
1.Conc.NaOH
Ph-CH3 1.CrO2Cl2 A B+C
2.H2O 2.H+
Select the correct statement(s) about B and C.
(A) Both give off H2 with Na.
(B) Only one of them gives off CO2 with NaHCO3.
(C) Only one of them gives positive Tollens test.
(D) None of them decolorises Br2/H2O.
42.
OH
H+/ Cold HIO4 OH-/
A B C D
KMnO4
Select the correct set of products
A D
A B
Q.No: 43 -45
A (CH ) CCOCH Br
(CH3 )3CCOCH 3 B (CH ) CCH(OH)CH Br
58% 3 3 2 54% 3 3 2
C (CH ) CCHCH
68% 3 3 2
CHEMISTRYWORLD.IN-9
A, B, and C are the reagents and percentage yield of each reaction is also given.
43. The best choice for A, B, & C is (A, B, & C respectively)
(A) HBr ; LiAlH4 then H2O ; RCO3H (B) Br2/H+ ; LiAlH4 then H2O ; RCO3H
(C) HBr ; LiAlH4 (D) Br2/H+ ; LiAlH4
44. If one mole of the starting compound is taken, the amount of the final product
obtained is
(A) 0.68mol (B) 0.22mol (C) 0.54mol (D) 0.58mol
45. Above conversion can be brought about in an alternate route. Select the best choice
of reagents in order of use in the alternate route.
(A) LiAlH4 then H2O ; H+/ ; RCO3H
(B) LiAlH4 then H2O ; POCl3/pyridine ; RCO3H
(C) Sn/HCl ; H+/ ; RCO3H D) None
KEY
1.A 2.A 3.B 4.B 5.A 6.A 7.B 8.D 9.B 10.A
11.A 12.D 13.C 14.A 15.A 16.B 17.A 18.A 19.B 20.A
21.D 22.B 23.D 24.C 25.B 26.B 27.BC 28.ABD 29.BCD 30.ABD
31.AB 32.AC 33.AB 34.ACD 35.ABCD 36.BD 37.CD 38AB 39.BD 40.AB
41.AB 42.BCD 43.D 44.B 45.B
CHEMISTRYWORLD.IN-10