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(A) (B)
(C) (D)
2. Which one among the following carbocations has the longest half-life?
(A) (B)
+
(C) (D) CH3 − C − CH3
|
CH3
(A) (B)
(C) (D)
5. Which of the following does not represent major product of that reaction?
(A)
(B)
(C)
(D)
(A) (B)
(C) (D)
(A) (B)
10.
(Styrene)
(A) Ph − C CNa (B) Ph − CH2 − C CH
(C) Ph − C C − CH3 (D) Ph − CH = C = CH2
11.
12. Select the reaction(s) that would result in the formation of 2-bromopropane.
I. CH3CH = CH2 + HBr ⎯⎯⎯⎯
peroxide
→ II. CH3CH = CH2 + HBr ⎯⎯⎯
CCl4
→
III. CH3CH2CH3 + Br 2 ⎯⎯
hv
→ IV. CH3CH = CH2 + Br2 ⎯⎯⎯
CCl4
→
(A) I and III (B) II and III (C) I, II and III (D) I and II
13.
(A) (B)
(C) (D)
(A) (B)
(C) Iso-butene > trans-2-butene > 1-butene (D) n-Hexane < n-Heptane < n-Octane
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
5. The correct statement(s) regarding isomers of a compound with general name trichlorocyclobutane
is(are):
(A) It has total seven isomers (B) It has two meso-isomers
(C) It has two optically active isomers (D) One isomer is devoid of any chiral carbon
6. Among the butane conformers, when viewed about C2 − C3 bond, which occur at energy minima on a
graph of potential energy versus dihedral angle?
(A) Gauche only (B) Gauche (C) Anti (D) Eclipsed
15. Which of the following will show optical isomerism as well as geometrical isomerism?
19. What is(are) true about the following two conformers of 2-fluoroethanol?
21. A solution containing stereoisomers A and B, is optically active. Which of the following statement(s)
concerning A and B can be true?
(A) A and B are enantiomers (B) A and B are diastereomers
(C) A and B are geometrical isomers (D) Neither A nor B contain any chiral carbon
22. The correct statement(s) concerning aldehydes of general formula C5H10O is(are):
(A) It has total five aldehyde isomers
(B) Two of the aldehydes are chiral
(C) Two of the aldehydes isomers have no enolic form
(D) All enols of aldehyde isomers are diastereomeric
23. In which of the following, enol form dominates over keto form?
(C) (D)
I. II.
29. In Lassaigne's test, the organic compound is first fused with sodium metal. The sodium metal is used
because:
(A) the melting point of sodium metal is low
(B) sodium reacts with elements of organic compound to form inorganic salts
(C) all sodium salts are water soluble
(D) sodium metal does not react with solvent water
30. Which of the following cannot be obtained as single major product in the Wurtz's coupling reaction of
halides with sodium metal?
(A) (B)
(C) (D)
31. Which of the following decarboxylation, reaction and their product is(are) incorrectly matched?
(A) (B)
(C) (D)
32. Which of the following reduction reaction and their product is(are) correctly matched?
(A) (B)
(C) (D)
33. What product(s) is(are) expected in the electrolysis of aqueous solution of potassium propanoate?
(A) Butane (B) Ethyl ethanoate
O O
|| ||
(C) Ethyl propanoate (D) CH3 − C − O − O − C − CH3
34. In the following free radical bromination reaction, the important product(s) is(are):
If a pure enantiomer of reactant is taken in the above reaction, the correct statement concerning product
dibromide is(are):
(A) A racemic mixture is formed
(B) Two optically active isomers are formed
(C) A pair of diastereomers in equal amount is formed
(D) A pair of enantiomers but in unequal amounts is formed
37. Which of the following reactions can bring about chlorination of cyclohexane?
Cyclohexane + Cl2 ⎯⎯⎯ → Cyclohexane + Cl2 ⎯⎯⎯
3→
Heat AlCl
(A) (B)
(C) Cyclohexane + SO2Cl2 ⎯⎯⎯
Heat
→ (D) Cyclohexane + HCl ⎯⎯
→
38. Which of the following reactions results in formation of an alkene?
(A) CH3 − CH2 − CHBr2 ⎯⎯⎯⎯
Zn
→ (B) CH3 − CH2 − CHBr2 ⎯⎯⎯
Ether
→
CH OH 3 Na/
Br
|
(C) CH3 − CH − CH2 Br ⎯⎯⎯⎯
Zn
CH OH
→ (D) CH2 − CH2 − CH2 ⎯⎯⎯⎯
Zn
CH3OH
→
3 | |
Br Br
39. Which of the following reaction(s) produces propene as one of the important organic product?
O
||
(A) CH3 − C − CH3 + Zn(Hg) ⎯⎯⎯ HCl
→
+
(B) CH3 − CH2 − CH2 − N(CH3 )3 Br − ⎯⎯⎯→
AgOH
42. In which of the following reaction(s), major product is formed by the rearrangement of reaction
intermediate?
(A)
(B)
(C)
(D)
(C) Z is
(A)
(B)
(C)
(D) H − C C − H ⎯⎯⎯⎯NaNH2
Liq. NH3
→ ⎯⎯→
D2
Pt
CH2 − CH2
| |
D D
45. Which is the important reactive intermediate in the following reaction?
46. In which of the following halogen addition reactions, racemic mixture of products is formed?
(A) (B)
47. Consider the following addition reaction on a pure enantiomer of the shown bromoalkene.
(A) (B)
(C) (D)
(A) (B)
(C) (D)
−
(A) Add one electron to -bond to give C9H10
2−
(B) Add two electrons to -bond to give C9H10
(C) Remove an ion, H+, from sp3 carbon
(D) Remove an ion, H+, from sp2 carbon
58. Which is true about the compound calicene?
(A) (B)
(C) (D)
64. The compound(s) that undergo slower electrophilic substitution than benzene is(are):
(A) (B)
(C) (D)
(A) (B)
(C) (D)
71. Which of the following alkene cannot be prepared by controlled hydrogenation of an alkyne?
(A) (B)
(C) (D)
72. Consider the following reaction,
73. Which of the following reactants, reagents and products are correctly matched?
(A)
(A) (B)
(C) (D)
75. Which of the following will evolve hydrogen gas on heating with potassium metal?
76. What product(s) are expected when excess of benzene is treated with 3-propenol in presence of HF?
(A) 3-phenyl propene (B) 1, 3-diphenyl propane
(C) 1, 2-diphenyl propane (D) 1, 1-diphenyl propane
2. An organic compound containing N, S, and O as extra elements is fused with metallic sodium and then
extracted with distilled water. Which species is not present in the Lassaigne’s extract?
(A) NO3− (B) CN − (C) CNS− (D) S2−
PARAGRAPH FOR QUESTIONS 3 - 5
Compound (A) (C13H24O) is a sex-attractant pheromone of codling moth. On hydrogenation, compound (A)
absorbs two molar equivalents of H2 and is converted to 3-ethyl-7-methyl-decan-1-ol. On reductive ozonolysis,
it gives the following compounds.
(A1)
The other isomer (A2) is:
(A)
(B)
(C)
(D)
(A)
(B)
(C)
(D)
1. Match the reactions from column I with the properties of their products from column II.
Column I Column II
4.
5.
6.
7.
1. ( A) ⎯⎯⎯
2H2
Pt
→
2. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the
alkane shown below is heated in the presence of Cl2 ?
3. 1.216 gm of an organic compound was reacted under Kjeldahl’s method and the ammonia evolved was
absorbed in 100 ml N H2SO4. The remaining acid solution was made up to 500 ml by the addition of
water. Twenty millilitres of this dilute solution required 32 ml of N/10 caustic soda solution for
complete neutralization. Calculate the percentage of nitrogen in the compound. (Nearest Integer)
4.
Sum of (P + Q + R + S + T) – 15 is ________.
(A) (B)
(C) (D)
If they are enantiomer answer will be 1, if they are diastereomers answer will be 2, if they are
constitutional isomers answer will be 3 and if they are identical use 4 as the answer. Sum of answer of
each part A + B + C + D is ________.
8. 1. 2.
3. 4.
9. How many carbon-hydrogen bond orbitals are available for overlap with the vacant p-orbital in ethyl
carbocation?
10. How many reagents from the following list will produce visible change when treated with propyne?
(I) H2 / Pt, Heat (II) K/ heat (III ) CH3MgBr (IV) Ag ( NH3 )+2
( V) Cu ( NH3 )+4 ( VI) Br2 − H2O ( VII) KMnO4 / HO− ( VIII) NaNH2
( IX) HCl ( X) O3 / H2O
11. How many different alkynes, on treatment with HgSO4 / H2SO4 can give 2-pentanone as one of the
product?
12. How many different cyclic isomers exist for the hydrocarbon C5H10 ?
13. If an aqueous solution containing both potassium ethanoate and potassium propanoate is subjected to
Kolbe’s electrolysis, how many products from the list below would be formed?
CH3CH3(I) CH3CH2CH3(II) CH3CH2CH2CH3(III) CH3COOC2H5(IV)
CH3CH3COOC2H5(V) CH3COOCH3(VI) CH3 CH2COOCH3(VII) CH4(VIII)
CH2 = CH2(IX) CH3CH=CHCH3(X)
14.
15. How many different six carbon hydrocarbons on reductive ozonolysis give the same product shown
below.
16.
17.
18.
19.
20.
21.
1 2 3 4 5 6 7 8 9 10
C A C B D C B B B C
11 12 13 14 15 16 17 18 19 20
B B B C C B C B C D
21 22 23 24 25 26 27 28 29 30
C A A C C D B D A B
31 32 33 34 35 36 37 38 39 40
C D C B A D C B C C
1 2 3 4 5 6 7 8 9 10
ABD AB ABC AB ABD BC AC AB BCD BD
11 12 13 14 15 16 17 18 19 20
CD AD ACD BD ACD BC ABD CD CD BD
21 22 23 24 25 26 27 28 29 30
ABCD ABD AB AD ABC ACD BC AC ABC AD
31 32 33 34 35 36 37 38 39 40
AB AD AC BC BC BC AC ABC BCD AC
41 42 43 44 45 46 47 48 49 50
BCD AD BCD AB BD ACD CD BC ABCD AB
51 52 53 54 55 56 57 58 59 60
D B ABD D AC ACD C AB AD BC
61 62 63 64 65 66 67 68 69 70
ABC BD AC BCD BC ABCD ABC AC ABD BC
71 72 73 74 75 76
AC BC ABD ABC AC ACD
1 2 3 4 5
C A B B B
1 2 3
[A-p, r] [B-q] [C-q, r] [D-p, s] [A-p, r] [B-q, s] [C-p, q, r] [D-p] [A-p, q] [B-r, s] [C-r, s] [D-p, q]
4 5 6 7
[A-P] [B-R] [C-S] [D-Q] [A-S] [B-R] [C-P] [D-R, S] [A-Q] [B-R] [C-S] [D-P] [A-Q] [B-P] [C-S] [D)-R]
1 2 3 4 5 6 7 8 9 10
9 8 23 90 4 13 9 312 3 8
11 12 13 14 15
2 7 9 4 2
1 2 3 4 5 6 7 8 9 10
11 12 13 14 15 16 17 18 19 20
21 22 23 24 25 26 27 28 29 30
31 32 33 34 35 36 37 38 39 40
1 2 3 4 5 6 7 8 9 10
11 12 13 14 15 16 17 18 19 20
21 22 23 24 25 26 27 28 29 30
31 32 33 34 35 36 37 38 39 40
41 42 43 44 45 46 47 48 49 50
51 52 53 54 55 56 57 58 59 60
61 62 63 64 65 66 67 68 69 70
71 72 73 74 75 76
1 2 3 4 5
1 2 3 4 5 6 7 8 9 10
11 12 13 14 15