Time Limit 60 Minutes

90 Marks

Q1.

2-Methylbutane can be obtained by catalytic hydrogenation of how many constitutional isomeric alkenes ? (a) 1 (b) 2 (c) 3 (d) 4 Which one is ambiguous name ? (a) Pentane (b) Neopentane (c) sec-Butanol (d) sec-Pentanol

Q2. Q3.

The correct order for increasing heat of combustion of the three hydrocarbons should be

(a) I < II < III Q4. Q5.

I (b) III < I < II

II (c) III < I < II

III (d) III < I < II

The total number of isomeric cyclic compounds of the molecular formula C5H10 having no dobule bond can be (a) 3 (b) 4 (c) 5 (d) 6 The maximum possible number of constitutional isomeric alkene (C6H10) that can be hydrogenated by catalytic hydrogenation to methylcyclopentane is (a) 3 (b) 4 (c) 5 (d) 6 The potential energy diagram for rotation of the C2 C 3 bond of butane through 360, starting with the least stable conformer is drawn below.
Potential energy

Q6.

60 240 360 120 300 0 180 The most stable conformer is obtained by rotation through a dihedral angle of (a) 60 (b) 120 (c) 180 (d) 360 Q7. Which of the following three alkenes is most stable ? I (a) I Q8. (b) II II (c) III III

(d) All are equal stable

The above three alkenes are hydrogenated to form alkenes Ia, IIa and IIIa respectively. Which of the alkane you expect to be most stable ? (a) Ia (b) IIa (c) IIIa (d) All are equal Methylcyclohexane can be prepared by the catalyte hyroenation of hou many isomeric alkenes ? (a) 1 (b) 2 (c) 3 (d) 4 The cis-and tans-2, 3-dichloro-2-butenes have different boiling points because the two isomers have (a) different dipole-dipole interactions (b) different van der walls interactions (c) both (a) and (b) (d) difference in H-bonding

Q9.

Q10.

Q11.

Br | CH3 OH CH3CH = CHCH2 CH CH2CH3 CH3CH = CHCH = CHCH2CH3 which of the statement is true regarding above reaction ? (a) It is an example of E2 reaction (b) It is an example of E1 reaction and involves the formation of 2 allylic carbocation (d) The reaction should be substitution

Q12.

NBS is used for brominating allylic carbon atom. Predict the product in the following reaction
CH2 Cl2
NBS, heat

CH2Br (a) Q13. Br (b) (c) Both (a) and (b) (d) Br

Br

Allylic substitution in CH3CH = CH2 may be carried out by (a) Sulphuryl chloride, SO2Cl2 (c) NBS
alc. KOH BrCH2CHBrCH3 Major product is ( HBr)

(b) tert-butyl hypochlorite, Me3COCl (d) All the three

Q14.

(a) CH2 = CBrCH3 (c) BrCH = CHCH3 Q15.

(b) CH2 = CHCH2Br (d) All the three in equivalent amount

The maximum number of possible products formed in the following reaction is CH3
heat + C2H5OH

Br (a) 2 (b) 3 CH3 (c) 4 (d) 5

Q16.

The correct IUPAC name for (a) 1, 5-dimethylcyclohexene (c) both are equally correct

Br is (b) 1, 4-dimethylcyclohexene (d) m-Dimethylcyclohexene

Q17.

An organic compound (C6H12) decolorizes Br2 and is oxidised by hot acidified KMnO4 to a resolvable carboxylic acid, C4H9COOH. The compound is CH3 CH3 CH3 | | | (a) CH2 C CHCH2 CH3 (b) CH2 C CH2 CH2 CH3 (c) CH2 CHCHCH2 CH3 (d) CH2 = CHCH2CH(CH3)2 | CH3 Which of the following cant be detected by bromine in carbon tetrachloride ? (a) Cyclohexene (b) 1, 3-Cyclohexadiene (c) Tetrachloroethene

Q18.

(d) None of the three

Q19.

Propene (I), 2-methylpropene (II), and ethene (III), each containing one carbon-carbon double bond, is separately treated with HI under the same set of conditions. The order of reactivity for the three alkenes should be (a) I > II > III (b) III > II > I (c) II > I > III (d) I = II = III C = CCH2CH2

Q20.

can best be prepared by which sequence of reaction Br C = CH (a) CH3CH2C CH + NaNH2 [ CH2CHBrCH2CH3 (c)
C2H5 ONa C2H5 OH

(b)

+ NaNH2 [

CH3 CH2 Br ]

(d) All the three

Q21.

4, 4-Dimethyl-2-pentyne can be synthesised by using CH3C = CH Me 3CBr Me 3CC = CH CH3I I II III IV (a) Combination of I and II in presence of NaNH2 (b) Combination of III and IV in presence of NaNH2 (c) either of the two (d) None of the two

Q22.

Arrange the following compounds in decreasing order of reactivity with Br2 CH2 = CH2 (I), CH = CH (II), CH2 = CHCl (III) (a) II > III > I (b) II > I > III (c) I > II > III

(d) All are equal

Q23.

Which reagent should be used for getting the following transformation in quantitative yield ? O | | CH3 C C H CH3 CH2 C H (a) Hg2+ / H2SO4 (b) BH2 THF; H2O2/OH (c) Sia2BH. THF; H2O/OH(d) Conversion not possible in a direct reaction Predict the major product in the following reaction : 1 HBr CH2 = CH C CH Product (a) CH3CH(Br)C CH (b) CH2 = CH C(Br) = CH2

Q24.

(c) Both

(d) CH2 = CH CH2 = CHBr

Q25.

Which of the following statements is true regarding the stability of following three dienes ? CH2 = CH CH = CH2 CH2 = CH CH2 CH = CH2 CH2 = C = CH CH3 (a) 1, 3-Butadiene is (a conjugated diene) is more stable than 1, 4-pentadiene (an isolated) due to resonance. (b) 1, 3-Butadiene is more stale than 1, 4-pentadiene becaue the former has a strong carbon-carbon single bond; while the latter has, two weaker carbon-carbon single bonds (c) 1, 2-Butadiene is less table than 1, 3-butadiene because the former has sp hybridised carbon atom (d) All the three Which of the dihydroxybutane can be converted casily into 1, 3-butadiene ? (a) CH3CH(OH)CH(OH)CH3 (b) HOCH2CH2CH2CH2OH (c) HOCH2CH2CH(OH)CH2OH (d) Both (b) and (c) Butadiene is treated with 1 equivalent of HBr at 80C, the major product will be (a) BrCH2CH = CHCH3 (b) CH3CHBrCH = CH2 (c) Both
peroxide CH2 = CH CH = CH2 + HBr (1 eq.) Product is (a) CH3CH = CHCH2Br (b) CH3CHBrCH = CH2

Q26.

Q27.

(d) Reaction not possible

Q28.

(c) Both (a) and (b)

(d) No reaction

Q29.

peroxide 1-Methyl-1, 3-cyclohexadiene + H2S (1 eq. ) Prodcut is

(a) Q30.

(b)

(c)

(d) No reaction

Which of the following does not involve the formation of an allylic carbocation ? (a) 1, 3-Butadiene + Br2 (b) 1-Chloro-2-butene + aq. AgNO3 (c) 3-Chloro-1-methylcyclopentene (d) None of the three