CLS Aipmt 17 18 XI Che Study Package 4 SET 2 Chapter 13

Chapter 13
Hydrocarbons
Solutions
SECTION - A
Objective Type Questions
1. The difference in potential energy between eclipsed and staggered form of ethane is
(1) 4 kJ/mol (2) 12.55 kJ/mol (3) 2 kJ/mol (4) 44 kJ/mol
Sol. Answer (2)
The energy difference between the eclipsed and staggered term of ethane is 12.55 kJ/mol
2. Eclipsed form of ethane has higher energy due to

(1) Torsional strain (2) Steric strain (3) Angle strain (4) Both (1) & (2)
Sol. Answer (4)
The eclipsed form of ethane possess higher energy and hence unstable. This is due to the torsional strain and
steric strain due to the repulsion between the electron clouds of the C-H bond.
3. The angle strain in cyclopentane is

(1) 72° (2) 1°28 (3) 44 (4) 108°
Sol. Answer (3)
1
Angle strain  d = 109.5 –  
2
1
= 109º 28 – 108º  [for cyclopentane a = 108º a = inner angle]
2
1º 28
=  44
2
4. Which one is most stable?

(1) Cyclopropane (2) Cyclobutane (3) Cyclopentane (4) Cyclohexane
Sol. Answer (4)
Cyclohexane is most stable because the ring is not planar but it is puckered in which all angles are tetrahedral
and thus cyclohexane ring is strainless.
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98 Hydrocarbons Solutions of Assignment (Set-2)
5. The chair form is _______ stable than boat form by potential energy _______ kJ/mol.
(1) More, 44 kJ/mol (2) Less, 44 kJ/mol (3) More, 12.55 kJ/mol (4) Less, 4 kJ/mol
Sol. Answer (1)
The chair form is more stable than boat form because in boat form, there is steric repulsion between flagpole
hydrogen and chain form is more stable by potential energy of 44 kJ/mol.
6. Which one is not aromatic compound?


(1) (2) (3) (4)
Sol. Answer (4)

Cyclopentadienyl cation is not aromatic because it contains 4n  electron where n = 1. Infact cyclopentadienyl
cation is an anti-aromatic cation.
7. The incorrect match is
(1) – Anti-aromatic (2) – Anti-aromatic

B
H
(3) – Non-aromatic (4) – Aromatic

Sol. Answer (2)
This compound is aromatic because it satisfies all the necessary conditions for aromaticity. These are 6
electrons (4 +2 electrons) planar structure, all carbons are sp2 hybridized and also the B atom is sp2 hybrid
and shows cyclic delocalization of electrons.
8. Which one of the following statement is not correct for sigma- and pi-bonds formed between two carbon atoms?
(1) Sigma-bond is stronger than a pi-bond
(2) Bond energies of sigma- and pi-bonds are of the order of 264 kJ/mol and 347 kJ/mol, respectively
(3) Free rotation of atoms about a sigma-bond is allowed but not in case of a pi-bond
(4) Sigma-bond determines the direction between carbon atoms but a pi-bond has no primary effect in this regard
Sol. Answer (2)
The bond energy of sigma bond is about 397 kJ/mol, where as the bond energy for pi bond is about 284 kJ/mol
sigma bond is stronger than pi bond.
CH3

9. A + NaOH CH3 – C – CH2 – CH3 ;
(CaO)
H
(Sodalime)
The possible compound A is
CH3 CH3
(1) CH3 – C – CH2COONa (2) CH3 – C – CH2 – CH2 – COONa
H H
CH3
(3) CH3 – CH2 – CH – CH2 – COONa (4) Both (2) & (3)
Solutions of Assignment (Set-2) Hydrocarbons 99
Sol. Answer (4)
CH3 CH3
NaOH
CH3 – C – CH2 – CH2 – COONa 
CaO
 CH3 – C – CH2 – CH3 + Na2CO3

H H 2-methylbutane
CH3 CH3
NaOH
CH3 – CH2– CH – CH2 – COONa 
CaO
 CH3 – CH2– CH – CH3

2-methylbutane
10. On electrolysis of sodium succinate, the alkene obtained is ______ and nature of solution after electrolysis is
______.
CH2 CH2 CH CH3
(1) and acidic (2) and basic (3) and acidic (4) and basic
CH2 CH2 CH CH3
Sol. Answer (2)
CH2–COONa electrolysis
+2H2O CH2 = CH2 + 2CO2 + H2
CH2–COONa
+2NaOH
Sodium succinate
The hydrocarbon formed is ethene and solution is basic due to the formation of NaOH.
11. Which one is not prepared by Wurtz reaction?

(1) C2H6 (2) n-C4H10
CH3 CH3
(3) CH4 (4) CH3 – CH – CH – CH3
Sol. Answer (3)
In Wurtz reaction the simplest alkane which can be prepared is C2H6, and it gives product with even number
of carbon atoms CH3Br + 2Na + BrCH3 
dry ether
CH3 – CH3 + 2NaBr
ethane
CH2CH3
12. can be prepared by
(1) Wurtz reaction (2) Fittig reaction (3) Wurtz Fittig reaction (4) Frankland reaction
Sol. Answer (3)
The reaction of an aromatic halide with aliphatic halide in presence of Na and dry ether to give alkyl benzenes
is called Wurtz fittig reaction
Br + 2Na + CH3CH2Br 

dry ether
CH2CH3 + 2NaBr
Na CH3Br
13. Mg2C3 + H2O A B C ;
The incorrect statement for C is
(1) Compound C is CH3 – C  C – CH3 (2) C gives positive Tollen's test
(3) In compound C all four carbon are linearly present (4) Compound C on ozonolysis gives diketone
Sol. Answer (2)
Na –+ CH3Br
Mg2C3 + H2O CH3–C  CH CH3–C  C Na B CH3–CC–CH3 C
A
Since compound C is not a terminal alkyne and does not contain acidic H.
14. In the following compounds the decreasing order of B.P. is

(I) CH3 – CH2 – CH2 – CH2 – CH2 – CH3,
CH3
(II) CH3 – CH – CH2 – CH2 – CH3,
CH3
(III) CH3 – C – CH2 – CH3,
CH3
(1) (I) > (II) > (III) (2) (I) > (III) > (II) (3) (II) > (III) > (I) (4) (III) > (II) > (I)
Sol. Answer (1)
With increase in branching boiling point decreases. This is due to decrease in the magnitude of van der Waals
forces with increase in branching. Therefore boiling point of n-hexane is higher than 2-methyl pentane and
2,2-dimethylbutane.
CH3
Cl2
15. CH3 – CH – CH2 – CH3 (A) ; The compound "A" is
UV light
Major
CH3 CH3
(1) CH3 – CH – CH – CH3 (2) CH3 – C – CH2 – CH3

Cl Cl
CH3 CH2Cl
(3) CH3 – CH – CH2 – CH2Cl (4) CH3 – C – CH2 – CH3

H
Sol. Answer (1)
Mechanism

hv
Cl2   2Cl
CH3 CH3
CH3 – CH – CH2 – CH3 +Cl CH3 – CH – CH – CH3 +Cl2
CH3
CH3 – CH – CH – CH3 + Cl
Cl
Selectivity for Cl2 is 1 : 3. 8 : 5 for 1º : 2º : 3º
MgBr
OD
16. + D2O A + Mg ;
Br
The compound A is
(1) Benzene (2) Duetero benzene (3) Duetero toluene (4) Both (2) & (3)
Sol. Answer (2)
MgBr D
OD
+ D2O + Mg
Br
Deutero benzene
17. In iodination ; for preparation of iodomethane compound used is

(1) HIO3 (2) HgO (3) Both (1) & (2) (4) HI
Sol. Answer (3)
Both HNO3 and HgO can be used for preparation of iodomethane because these oxidizes the HI formed as

one of the product to shift the reaction in the forward direction CH4  I2
CH3I  HI
18. In chlorination the relation rate of abstraction of H in 3°, 2° and 1°C atom respectively
(1) 5 : 3.8 : 2 (2) 5 : 3.8 : 1 (3) 1600 : 82 : 1 (4) 1600 : 5 : 82
Sol. Answer (2)
The chlorination of alkanes proceeds through the formation of alkyl free radical and the order of stability of free
radical is 3º>2º>1º, 3º radical is more stable because it has more number of Hyper conjugative structures.
Therefore the relative rate of abstraction of H in 3º, 2º and 1º C atom is 5 : 3.8 : 1.
19. In which alkane isomerization will not occur?

(1) C2H6 (2) C4H10 (3) C5H10 (4) C6H14
Sol. Answer (1)
H H
In ethane, isomerization is not possible because it contains only two carbon atoms H–C–C–H
H H
OH
H3PO4
20. In "A" ; compound "A" is
 Major
CH2 O
(1) (2) (3) (4)
Sol. Answer (2)

+
OH OH2 +
H +
+
H3PO4 –H3O –H

Na/liq. NH3
21. CH3 – C  C – CH3 A ;
Pd/CaCO3
B ;
(CH3COO)2Pb
The minimum heat of hydrogenation is in
(1) A (2) B (3) Both have equal (4) Cannot predict

Sol. Answer (1)
Na/liq. NH3 CH3 H

CH3 – C  C – CH3 C=C
H CH3
Pd/CaCO 3 CH 3 CH3
(CH3COO)2Pb C=C
H H
cis-2-butene
Trans 2-butene will show minimum heat of hydrogenation because trans 2-butene is more stable as compared
to cis 2-butene.
CH2
22. CCl4
+ HBr "A" ;
High temperature
The compound A is
CH2 CH2Br CH2Br

(1) (2) (3) (4)
Br Br
Sol. Answer (2)
CH2 CH3 CH3 CH3

+ –
+
CCl4 Br
+H High temp. +
Br
A
23. In which of the following reactions Markovnikov’s rule is not observed ?

(1) CH3CH = CH2 + HCl ——————
organic peroxide, h
(2) CH3CH = CH2 + HBr  
H2O2, h
(3) CH3CH = CH2 + HBr 
(4) Both (2) & (3)

Sol. Answer (4)
Markovnikov’s rule is not followed when free radical additon of HBr takes place to an unsymmetrical alkene
organic peroxide
CH3–CH = CH2 + HBr 
h CH3 – CH2 – CH2 – Br
H2O2, h
CH3–CH = CH2 + HBr  CH3 – CH2 – CH2 – Br
Both these reactions follow free radical mechanism and hence Markovnikov’s addition is not observed.
24. The reaction of CH3CH = CH2 with HOCl will yield
(1) 2-chloro-1-propanol (2) 3-chloro-2-propanol
(3) 1-chloro-2-propanol (4) 1-chloro-1-propanol
Sol. Answer (3)
OH
CH3 – CH = CH2 + HOCl CH3 – C H – CH2 – Cl
1-chloro-2-propanol
Mechanism
– +
HOCl HO + Cl
OH
+ + –
CH3 – CH = CH2 + Cl CH3 – CH – CH2 – Cl + OH CH3 – CH – CH2 – Cl
25. C6H5CH2CH2CH3 is when oxidised in the presence of alk. KMnO4, the product obtained is
(1) C6H5CHO (2) C6H5COOH (3) C6H5CH2CH2CHO (4) C6H5COCH3
Sol. Answer (2)
CH2CH2–CH3 COOH
Alkaline
KMnO4
Benzoic acid
Alkaline KMnO4 is a strong oxidizing agent and oxidizes alkyl benzenes to benzoic acid.
26. What is X in the following sequence of reactions?
Na NaOH / CaO
X 
 Z    CH4
1 / 2H2
(1) Methane (2) Ethanoic acid (3) Propane (4) None of these
Sol. Answer (2)
Na NaOH/CaO
CH3 COOH   CH3 COONa 
Decarboxylation
 CH4  Na2 CO3
1/2H2
27. Addition of HBr to propene

(1) Follows Markovnikov’s rule
(2) Does not follow Markovnikov’s rule
(3) Follows Markovnikov’s rule but the product rearranges to give anti–Markovnikov’s product
(4) Follows free radical mechanism
Sol. Answer (1)
Br
CH3 – CH = CH2 + HBr CH3 – CH – CH3
When HBr is adds to propene, Markovnikov’s rule is obeyed. However in the presence of peroxide, free radical
addition of HBr to propene takes place which does not follow Markovnikov’s rule.
28. In an attempt to prepare propane by Wurtz reaction 1 mole of methyl bromide and 1 mole of ethyl bromide
are treated with sodium. Assuming equal probability for all possible reaction. How many g of propane will be
obtained?
(1) 44 g (2) 22 g (3) 33 g (4) 14.67 g
Sol. Answer (4)
The possible reacts are
(i) CH3Br + 2Na + CH3Br  CH3– CH3 + 2NaBr
(ii) CH3Br + 2Na + CH3CH2Br  CH3CH2CH3 + 2NaBr

(iii) CH3CH2Br + 2Na + CH3CH2Br  CH3–CH2–CH2 –CH3 + 2NaBr
1 mol of CH3CH2CH3 weight = 44g
44
Grams of CH3CH2CH obtained =
3
= 14.67g
1 1
Since 3 reactions of possible, the probability of formation of propane is and mass of propane obtained is of
3 3
mass of mass of 1 mol of propane i.e, 14.67 g
29. Addition of HBr to 2-methyl-1-propene in the presence of hydrogen-peroxide produces

(1) 1-Bromobutane (2) 2-Bromopropane
(3) 2-Bromo-2-methylpropane (4) 1-Bromo-2-methylpropane
Sol. Answer (4)
Mechanism

UV
R–O–O–R 
 2R – O
 
HBr + R O  R – OH  Br
HBr
+ Br + Br
Br Br
K Cr O
30. Toluene 
2 2 7
Y . Here Y is
H2SO 4
(1) Benzaldehyde (2) Toluene (3) Benzoic acid (4) Ethylbenzene

Sol. Answer (3)
CH3 COOH
K2Cr2O 7
H2SO4
Toluene Benzoic acid Y
Acidified K2Cr2O7 is an strong oxidizing agent and its oxidizes –CH3 group of toluene to –COOH group
AlCl
31 . C6H6  Z 
3
 Toluene, Z is
(1) Acetic acid (2) Acetic anhydride (3) Acetone (4) Chloromethane
Sol. Answer (4)
CH3
AlCl3
+ CH3Cl
(C6H6) Toluene

–
CH3Cl  AlCl4  CH3  AlCl4
CH3 CH3
+ +
H –H
+
+ CH3
Toluene
32. C 6 H 6    X . Here, X is
Oxidation
V2O 5 / 
(1) Maleic anhydride (2) Acetic acid (3) Propanoic acid (4) Succinic acid
Sol. Answer (1)
O
Oxidation CH–COOH  CH–C

V2O5
O
CH–COOH –H2O CH–C
O
Maleic anhydride
33. In Kharasch effect; reaction follows

(1) Free radical substitution (2) Electrophilic addition
(3) Free radical addition (4) Nucleophilic addition
Sol. Answer (3)
Kharasch effect is the anti-Markovnikov's addition of HBr to an unsymmetrical alkene in the
presence of peroxide. This reaction follows free radical addition.
O O O
Homolysis
C6H5–C–O–O–C–C6H5 
2C6H5–C–O
Free Radical
C6H5COO+HBr C6H5–COOH+Br
Bromine Free Radical
CH3– CH =CH 2+Br CH3–CH– CH2–Br+HBr CH3–CH2–CH2––Br+Br
(1) B2H6
34. "A" ; "A" is
(2) H2O2/OH (Major)
OH
OH
(1) (2) OH (3) (4)
OH
Sol. Answer (1)
–
B2H 6 H2O2OH
BH2 OH
Hydrobaration oxidation results in the anti-Markownikov's additon of water to alkene.
Cl
Potassium tert. butoxide
35. CH3–CH–CH2–CH3 "A" is
Major
(1) CH3 – CH = CH – CH3 (2) CH2 = CH – CH2 – CH3
CH3
(3) CH3 – C = CH2 (4) Both (2) & (3)
Sol. Answer (2)

Cl Cl
CH2–CH–CH2–CH3 CH2 CH–CH2–CH3
CH3 –
H CH3 CH2=CH–CH2–CH3+(CH3)3C–OH+Cl
– H O–C–CH3
O–C–CH3
CH3
CH3
CH3
36. C KMnO4 + H2SO4 NaOH ;

A CaO
B
CH
Compound B is
(1) C2H6 (2) CH4 (3) CH3COOH (4) CH3COONa
Sol. Answer (2)
NaOH
CH3–C CH KMnO4 + H2SO4 CH 3–COOH CH4
Oxidation CaO
Decarboxylation
CH2 Turns CuSO 4

crystal to blue
(1) KMnO 4/
37. + A + B +C ;
(2) H
Turns lime H2O milky
Compound A , B and C are respectively
O O
(1) CH2O, H2O and (2) , CO2, H2O
O CHO
(3) , SO2, H2O (4) , CO2, H2O
Sol. Answer (2)
CH2 O
(1) KMnO4/
+ + CO2 + H2O
(2) H
(A) (B) (C)
CO2 turns lime water milky and H2O turns CuSO4 crystals to blue due to formation of hydrated salt.
CH3
CH3 (1) O3
38. C = C – CH = CH2 A + B + C;
CH3 (2) Zn/H2O
Which one is not A , B , C ?
O O
(1) CH3 – C – CH3 (2) CH2O (3) CH3 – C – CHO (4) CH3CHO
Sol. Answer (4)
Ozonolysis of alkene results in oxidative cleavage
CH3 O CH3 O O
CH3 (1) O3 CH3 Zn/H2O
C = C – CH = CH2 C C – CH CH2 CH3–C–CH3 + CH3–C–CHO + HCHO
CH3 (2) Zn/H2O CH3
O O O O A BO C
Hence CH3CHO is not formed.
CH3
CH3 (1) O3
39. A + B + C ;
(2) Zn/H2O
A , B and C can be
O O O
CHO
(1) CH3 – C – C – CH3 (2) (3) CH3 – C – CHO (4) All of these
CHO
Sol. Answer (4)
O O O
CHO
CH3 – C – CHO, CH3 – C – C – CH3 and are formed.
CHO
40. Baeyer’s reagent is

(1) 1% Alkaline KMnO4 (2) Acidic KMnO4 (3) Neutral KMnO4 (4) Aq. Br2 solution
Sol. Answer (1)
1% alkaline solution of KMnO4 is known as Baeyer's reagent.
41. Acetylene when oxidized with chromic acid gives
(1) Ethylene glycol (2) Oxalic acid (3) Formic acid (4) Acetic acid
Sol. Answer (4)
CH H2CrO4
+[O]+H2O CH3COOH

CH
acetylene acetic acid
42. The catalyst used to reduce an alkyne to alkene is

(1) Raney Nickel (2) Palladium (3) Lindlar’s catalyst (4) Iron
Sol. Answer (3)
Lindlar’s catalyst is palladium deposited on CaCO3/BaSO4 which is poisoned with lead or sulpher compounds.
It is used for the hydrogenation of alkyne to alkene in suitable solvent.
H2, Pd–BaSO4
R–CCH R–CHCH2
Lindlar's catalyst
Alkyne Alkene
43. Benzene undergoes substitution reaction more easily than addition because
(1) It has a cyclic structure (2) It has three double bonds
(3) Of delocalization of -electrons (4) It has six hydrogen atoms
Sol. Answer (3)
Benzene consist of sp2 hybridized carbon atoms whose -charge cloud is delocalized over the ring.
Because of the high stability of benzene due to aromaticity, it does not show addition reaction but since it
contain electron charge cloud, it shows electrophilic substitution reaction.
44. A mixture of C2H6, C2H4 and C2H2 is bubbled through alkaline solution of copper (I) chloride, contained in Woulf’s bottle.
The gas coming out is
(1) Original mixture (2) C2H6 (3) C2H6 and C2H4 mixture (4) C2H4 and C2H2
Sol. Answer (3)
Out of C2H6, C2H4 and C2H2, C2H2 will react with alkaline Cu2Cl2. Therefore only C2H6 and C2H4 will come out
of the bottle.
alkaline
CHCH+Cu2Cl2 C2Cu2+2NH4Cl+2H2O
NH4OH
45. Ethylene + S2Cl2  "A" ; The compound "A" is
(1) Lewisite (2) Mustard oil (3) Mustard gas (4) Insecticide
Sol. Answer (3)
S2Cl2+2 C2H 4Cl–CH2–CH2–S –CH2–CH2–Cl+S

Mustard gas
Hg2+, H+/H2O
46. Ph – C  CH "A" .
Addition of H2O in the reaction is an example of
(1) Electrophilic addition (2) Nucleophilic addition
(3) Free radical addition (4) Electrophilic substitution
Sol. Answer (2)
2+
+
Ph – C  CH+Hg Ph – C  CH Ph – C  CH
Hg2+ Hg2+
H
+
O H + OH OH O
+ Nucleophilic –H H2O
Ph – C = CH + O–H attack Ph – C  CH Ph – C  CH Ph – C  CH2 Ph – C – CH3
+ + A
Hg
H
2+ Hg Hg
47. Monomer of neoprene is

(1) Chloroprene (2) Acetylene (3) Vinyl acetylene (4) Both (2) & (3)
Sol. Answer (1)
Cl Cl
Polymerisation
n CH2=C–CH=CH2 ( CH2–C=CH–CH2 ) n
chloroprene Neoprene
(Polychloroprene)
+ –
N2 Cl
48. A + N2 + HCl
Compound "A" is
(1) H3PO2 (2) H3PO3 (3) H3PO4 (4) Both (1) & (2)
Sol. Answer (4)
Both H3PO2 and H3PO3 can be used to convert benzene diazonium chloride to benzene.
+
H
49. + CH3 – CH = CH2 A .
Compound "A" is
(1) Isopropyl benzene (2) Cumene
(3) An alkyl derivative of benzene (4) All of these
Sol. Answer (4)

+ +
CH3 – CH = CH2 + H CH3 – CH – CH3
CH3 CH3
+ CH + CH
CH3 –H CH3
+ CH3–CH–CH3 +
H
cumene
cumene is also known as isopropyl benzene which is an alkyl benzene.
50. In sulphonation of benzene; electrophilic reagent used is
O
 
(1) SO H (2) SO3 (3) O=S=O (4) SO2OH
3

Sol. Answer (2)
+ –
H2SO4 + H2SO4 H3O + HSO4 + SO3
– –
SO3 SO3 SO3H
+H – +
HSO4 H3O
+ SO3
–H2SO4
51. Which one is o, p-directing group for electrophilic substitution reaction?
O O
CH3
(1) – C – OH (2) – C – NH2 (3) – N (4) – NO2
CH3
Sol. Answer (3)
–N(CH3)2 is an electron donation group. It is an ortho and para directing group for electrophilic substitution
O O
reaction. –C–NH2, –C–OH and –NO2 are electron withdrawing group. They are meta directing group for
electrophilic substitution reaction.
52. In Chlorobenzene, 2,4-dinitrochlorobenzene ,

(I) (II)
p - nitrochlorobenzene
(III)
The decreasing order of reactivity towards electrophilic substitution reaction is

(1) (I) > (II) > (III) (2) (I) > (III) > (II) (3) (II) > (I) > (III) (4) (III) > (I) > (II)
Sol. Answer (2)
Reactivity
Cl Cl Cl
NO2
> >
NO2 NO2
–NO2 group is an electron withdrawing group and its decreases the electron density on benzene ring due to
its –R and –I effect. Since chlorobenzene does not contain nitro group it is most reactive towards electrophilic
substitution, since p-nitrochlorobenzene contains only one nitro group, it is more reactive towards electrophilic
substitution reaction as compared to 2, 4-dinitrochlorobenzene.
HI
53. CH3 – CH = CH – CH2 – CH3 A ;
Major
Compound A is
(1) CH3 – CH2 – CH – CH2 – CH3 (2) CH3 – CH – CH2 – CH2 – CH3
I I
CH3 CH3
(3) CH3 – C – CH2 – CH3 (4) CH3 – C – CH2I
I CH3
Sol. Answer (2)
+
H + +
CH3 – CH = CH – CH2 – CH3 CH3 – CH – CH2– CH2 – CH3 (major) + CH3 – CH2 – CH – CH2 – CH3 (minor)
(I) (II)
+ –
CH3 – CH – CH2 – CH2 –CH3+I CH3 – CH – CH2 – CH2 – CH3
I
Carbocation (I) is more stable than carbocation II because I has more number of hyperconjugating structures.
54. The electrophile which attacks in Friedel-Craft acylation is
O
–
O O
(1) R – C  (2) R – C (3) R – C – O – (4) Both (1) & (3)
+
Sol. Answer (1)
O O
R – C – Cl + AlCl3 R – C+ AlCl4–
O O
O
C–R AlCl4 C–R
+ R–C  + HCl + AlCl3
H
55. Which of the following shows geometrical isomerism?

(1) But-1-ene (2) But-2-ene (3) Prop-1-ene (4) Pent-1-ene
Sol. Answer (2)
CH3 CH3 CH3 H

C=C C=C
H H H CH3
Cis. but-2-ene Trans. but-2-ene
SECTION - B
Objective Type Questions
A
1. CH3 CH CH CHO CH 3 CH CH CH3
The best suitable reagent 'A' is

(1) C3H8S2/H2/Ni (2) N2H4/KOH (3) Zn–Hg/conc. HCl (4) HI/P(red)
Sol. Answer (2)
N2H2
CH3 CH CH CHO KOH
CH3 CH CH CH3
This is known as Wolff-kishner reduction it specifically converts/reduces carbonyl group to –CH2 or CH3 group
without affecting the double bond.
CHO CHO
2.
C CH C CH
The most suitable reagent for given conversion is

(1) Diimide (2) H2/Ni2B (3) Zn/dil. HCl (4) LiAlH4
Sol. Answer (1)
Dimide are specifically used to hydrogenate the alkenes. The advantage of using diimide is that they does not
react with triple bond or functional group present with the double bond.
CHO CHO
H–N=N–H
+ N2
Diimide
C CH C CH
3. Consider the following two structures
(i) (ii)
Choose the correct statement

(1) Both (i) & (ii) are conjugated system (2) (i) & (ii) both show resonance
(3) (i) & (ii) both are aromatic (4) (i) is less stable than (ii)
Sol. Answer (1)
Benzene is an aromatic compound having conjugated double bonds and it is highly stable due to resonance.
Cyclooctatetraene (stucture ii) on the other hand is a non-aromatic compound which is not planar and hence
it does not exihibit resonance despite of having conjugated double bonds.
H
4. CH3 C C C C
H C C CH3
H2/Pd — BaSO4 Na/NH3(l)

(One equivalent)
A B
In above reaction product (B) is
(1) (2) (3) (4)
Sol. Answer (4)
H
H H
CH3 C C C C H2/Pd — BaSO4 C C
C C CH3 (One equivalent) CH3 CH = CH
H C C – CH3
Na/NH3(l)
H H
C C
CH3 CH = CH H
C=C
H CH3
Trans
H2/Pd-BaSO4 (Lindlar's catalyst) reduces/hydrogenates alkyne to give cis-alkene whereas Na/NH3 (liquid)
hydrogenates alkyne to give trans alkene.
5. In the given reaction
CHO N2H4/H2O2
Product
CH3
The product will be
CHO CH3 CHO

H H H
(1) H (2) H (3) CH3 (4) Mixture of (1) & (2)
CH3 CH3 H
Sol. Answer (1)

When N2H4 is treated with an oxidizing agent, it produces diimide which hydrogenates double bond and follows
syn addition.
CHO
CHO H CHO
N
N2H4 syn H +N
H2O2 N addition H 2
CH3 H
CH3 CH3
Overall result is the syn addition of H2 to the double bond.
Na O3 Zn — Hg/conc. HCl
6. NH3(l)
A Zn — H2O
B C
major
Product (C) is
(1) Mixture of n-butane, ethane (2) Only propane
(3) Only ethane (4) n-hexane
Sol. Answer (2)
Na O3 Zn — Hg/conc. HCl
OHC – CH2 – CHO CH3 – CH2 – CH3
NH3(l) Zn — H2O +
+
CH3 – CH2 – CH3
OHC – CH2 – CHO
Propane
The end product of this reaction sequence is propane only.
7. Natural rubber is a polymer of isoprene (2-methyl buta-1, 3-diene). If natural rubber is treated with O3 followed by
Zn/H2O, the final product will be
O
O
H C
(1) C O (2) CH3 C CH2 CH2 CHO
H
O O
O H
H C C H
(3) CH3 CH2 C CH2 CHO (4) CH2 C
CH3
Sol. Answer (2)
O
CH3 H O3
CH3 H )
C=C CH2 CH2 C=C
CH2 Zn.H2O OHC – CH2 – CH2 – C – CH3
( CH2 CH2 C=C CH2
CH3 H
O3/Zn — H2O
8. C3H4 CO2 + HCHO Product (C) is
2 eqv. HCl (1) alc. KOH

A B 2+ + C (major)
(2) NaNH2 Hg /H3O
+
(3) H
(1) Propanal (2) Butanal (3) 2-pentanone (4) Propanone

Sol. Answer (4)
O3/Zn — H2O
CH2 = C = CH2 2HCHO + CO2
C3H4
Cl 2+
OH O
2 eqv. HCl (1) alc. KOH Hg
CH3–C–CH3 CH3–C CH + CH3–C =CH2 CH3–C =CH3
(2) NaNH2 H3O (Propanone)
Cl (3) H
+
9. In the given reaction
O
COOH CH3
HI
Red P
OH
The number of moles of HI required for conversion is
(1) 12 (2) 8 (3) 14 (4) 10
Sol. Answer (1)
1 mole of carbonyl or –OH group utilizes 4 moles of HI for their conversion into hydrocarbon
O
Red P
R – C – R + 4HI  R – CH2 – R + H2O + 2I4
Since the given compound contain 3 group which can undergo reduction, It will require 12 moles of HI for the
given conversion.
10. Dehydration by conc. H2SO4 is the most difficult in

OH
OH
(1) (2) CH3 (3) (4)
CH3 OH CH3 CH2OH
Sol. Answer (3)

The dehydration of alcohols by conc. H2SO4 involves the formation of carbocation.

OH OH2

conc. H2SO4 –H2O
CH3 CH3 CH3

The above compound gives a bridgehead carbocation on dehydration. Since bridgehead carbocations are very
unstable because of their non-planar structure, the dehydration of this compound with H2SO4 is very difficult.
11. Which of the following can form methane gas with methyl magnesium bromide?
CH3
(1) (2) (3) (4)
Sol. Answer (2)

Methyl magnesium bromide reacts with compound having acidic hydrogen to form methane gas
for example CH3MgBr + AH  CH4 + AMgBr [AH = Aad]
Cyclopentadiene can loose a proton and acts as an acid, because cyclopentadienyl anion formed after loosing
a proten is avite stable because of its aromatic nature.

–H
Cyclopentadienyl anion (Aromatic)
Since the conjugate base is stable, cyclopentadiene can loose a proton and will give methane gas on reaction
with CH3MgBr.
CH3 CH3 CH2

12. C C A
H H
CH2
B
A & B are respectively
H H H CH3 CH 3 H H CH3 H CH3 CH 3 H

(1) , mixture of & (2) , mixture of &
CH 3 CH3 CH3 H H CH3 CH 3 H CH3 H H CH3
CH3 H H
CH3 H H CH3 H H
CH3 H CH3
(3) Mixture of , (4) Mixture of ,
H CH3 CH3 H CH3 CH3 H CH3 CH3 H CH3 H
Sol. Answer (1)
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

C C C C C C
H H H H H H or H H
CH2 CH2 cis-compound
CH2
A
Singlet carbene
CH3 CH3 CH3 CH3 CH3 H

Rotation about
C C + CH2 C C C-C bond C C
H H triplet carbene H H H CH3
CH2 CH2
1 CH3 H H CH3 CH3 H

Spin
CH3 H Ring
C C closure
C C
Inversion or CH3 H and H CH3
H CH3 H CH3
1 CH2 CH2
B
13. Which of the following compound is paramagnetic?


–
+
(1) (2) (3) (4)
Sol. Answer (1)

Antiaromatic compounds are paramagnetic in nature cyclobutadiene is an antiaromatic compound because it
has cyclic planar structure but has 4 electrons.
H2O Cu2Cl2 (1) 1 eqv. HCl

14. CaC2 A NH4Cl
B (2) Mg/ether
C
+
(3) CO2/H2O/H
In above reaction product (C) is

(1) CH2 ==CH—COOH (2) HC C—COOH
(3) HOOC—CC—COOH (4) CH 2 CH C CH2
COOH
Sol. Answer (4)
H2O Cu2Cl2 HCl

CaC2 CH  CH + Ca(OH)2 NH4Cl
CH2 = CH – C  CH CH2 = CH – C  CH2
Cl
Mg/ether CO2/H2O
CH2 = CH – C = CH2 + CH2 = CH – C = CH2
H
MgCl COOH
15. In which of the following dehydration by conc. H2SO4 no rearrangement is favourable?
CH2OH CH2OH
(1) (2)
CH2OH CH3 CH3
(3) (4) OH
Sol. Answer (1)

Dehydration of alcohols with conc. H2SO4 involves the formation of carbocation. In the dehydration of compound
I rearrangement is not possible because cyclopropyl ring strongly stabilizes the carbocation (II) and
rearrangement is not favourable because of high stability of carbocation (II)
 
CH2OH CH2OH2 CH2
H2SO4 –H2O
(I) (II)
SECTION - C
Previous Years Questions
1. Predict the correct intermediate and product in the following reaction
H2O, H2SO4
H 3C C CH HgSO4
intermediate product [NEET-2017]
(A) (B)
(1) A : H3C C CH2 B : H3C C CH3 (2) A : H3C C CH2 B : H3C C CH2
SO4 O OH SO4
(3) A : H3C C CH3 B : H3C C CH (4) A : H3C C CH2 B : H3C C CH3
O OH O
Sol. Answer (4)
OH O
H2O, H2SO4 Tautomerism
H3C – C  CH H3C – C = CH CH3 – C – CH3
HgSO4
(A) (B)
2. Which one is the correct order of acidity? [NEET-2017]

(1) CH2 = CH2 > CH3 – CH = CH2 > CH3 – C  CH > CH  CH
(2) CH  CH > CH3 – C  CH > CH2 = CH2 > CH3 – CH3
(3) CH  CH > CH2 = CH2 > CH3 – C  CH > CH3 – CH3
(4) CH3 – CH3 > CH2 = CH2 > CH3 – C  CH > CH  CH
Sol. Answer (2)
Correct order is
H – C  C – H  H3 C – C  C – H  H2 C CH2  CH3 – CH3

(Two acidic (One acidic
hydrogens) hydrogen)
3. With respect to the conformers of ethane, which of the following statements is true? [NEET-2017]
(1) Bond angle remains same but bond length changes
(2) Bond angle changes but bond length remains same
(3) Both bond angle and bond length change
(4) Both bond angles and bond length remains same
Sol. Answer (4)
There is no change in bond angles and bond lengths in the conformations of ethane. There is only change in
dihedral angle.
4. Which of the following can be used as the halide component for Friedel Crafts reaction?
[NEET(Phase-2)-2016]
(1) Chlorobenzene (2) Bromobenzene (3) Chloroethene (4) Isopropyl chloride
Sol. Answer (4)

Isopropyl chloride would form stable carbocation H3C — C — CH3
H
5. Which of the following compounds shall not produce propene by reaction with HBr followed by elimination or
direct only elimination reaction? [NEET(Phase-2)-2016]
H2 H2
(1) H2C CH2 (2) H3C C CH2OH (3) H 2C C O (4) H3C C CH2Br
C
H2
Sol. Answer (3)
H 2C C O , has only two carbon atom, cannot be converted into propene as the conditions are given.
HF
6. In the given reaction + 0°C P , the product P is [NEET(Phase-2)-2016]
F F
(1) (2) (3) (4)
Sol. Answer (3)
HF 
–H
7. The compound that will react most readily with gaseous bromine has the formula [NEET(Phase-2)-2016]
(1) C3H6 (2) C2H2 (3) C4H10 (4) C2H4

Sol. Answer (1)
In gas phase allylic substitution takes place.
8. The correct statement regarding the comparison of staggered and eclipsed conformations of ethane is
[NEET-2016]
(1) The staggered conformation of ethane is more stable than eclipsed conformation, because staggered
conformation has no torsional strain
(2) The staggered conformation of ethane is less stable than eclipsed conformation, because staggered
conformation has torsional strain
(3) The eclipsed conformation of ethane is more stable than staggered conformation, because eclipsed
conformation has no torsional strain
(4) The eclipsed conformation of ethane is more stable than staggered conformation even though the eclipsed
conformation has torsional strain
Sol. Answer (1)
Fact.
(1) NaNH2 /liq. NH3 (1) NaNH2 /liq. NH3
9. In the reaction, H – C  CH 
(2) CH CH Br
X 
(2) CH CH Br
Y . X and Y are [NEET-2016]
3 2 3 2
(1) X = 1-Butyne; Y = 2-Hexyne

Sol. Answer (2)
(1) NaNH /liq. NH (1) NaNH2 /liq. NH3
H – C  CH 2
(2) CH3CH2Br
3
H – C  C – CH2 – CH3  CH3 – CH2 – C  C – CH2 – CH3
(2) CH CH Br
(1Butyne ( X)) 3 2
(3-Hexyne (Y))
10. Consider the nitration of benzene using mixed conc. H2SO4 and HNO3. If a large amount of KHSO4 is added
to the mixture, the rate of nitration will be [NEET-2016]
(1) Doubled (2) Faster (3) Slower (4) Unchanged
Sol. Answer (3)

 –
HNO3  H2 SO 4
NO2  HSO 4  H2 O
 Addition of KHSO4 will decrease the NO2+ concentration.
11. In the reaction with HCl, an alkene reacts in accordance with the Markovnikov's rule, to give a product 1-chloro-
1-methylcyclohexane. The possible alkene is [Re-AIPMT-2015]
CH2 CH3 CH3
(1) (A) (2) (B) (3) (A) and (B) (4)
Sol. Answer (3)

Markovnikov's rule more EN part attack's on unsaturated hydrocarbon which have less number of hydrogen.
CH2 CH3
Cl
HCl
AlC to M.R.
CH3 CH3
Cl
HCl
AlC to M.R.
12. A single compound of the structure
CH3 CH3
OHC C C
H
C C O
H2 H2
is obtainable from ozonolysis of which of the following cyclic compounds? [AIPMT-2015]
H3C H3C CH3

H3C
(1) CH3 (2) CH3 (3) (4)
H3C
CH3
Sol. Answer (2)
CH3
CH3 CH3 CH3 CH3 CH3
O3 /Zn O O
O CH2
O O C
H
Or
CH3 CH3 CH3 CH3

O3/Zn O CH3 CH3
O or OHC CH2 CH C O
13. The reaction of C6H5CH = CHCH3 with HBr produces [AIPMT-2015]
CH = CHCH3
(1) (2) C6H5CHCH2CH3
Br
Br
(3) C 6H 5CH2CHCH 3 (4) C6H5CH2CH2CH2Br
Br
Sol. Answer (2)
HBr + –
C6H5 CH CH CH3 C6H5 CH CH CH3
HBr
C6H5 CH CH2 CH3
Br
14. Which of the following organic compounds has same hybridization as its combustion product-(CO2) ?
[AIPMT-2014]
(1) Ethane (2) Ethyne (3) Ethene (4) Ethanol
Sol. Answer (2)
15. Which of the following reagents will be able to distinguish between 1-butyne and 2-butyne ?
[AIPMT (Mains)-2012]
(1) NaNH2 (2) HCl (3) O2 (4) Br2
Sol. Answer (1)
Terminal alkynes are acidic in nature and reacts with base because they contain acidic hydrogen.
CH3 – C  C – CH3 + NaNH2  No reaction.
CH3 – CH2 – C  CH + NaNH2  CH3 – CH2 – C CNa + NH3
Since 2-butyne does not contain acidic hydrogen, it will not react with base (NaNH2)
16. Liquid hydrocarbons can be converted to a mixture of gaseous hydrocarbons by [AIPMT (Prelims)-2010]
(1) Oxidation
(2) Cracking
(3) Distillation under reduced pressure
(4) Hydrolysis
Sol. Answer (2)
Distillation is a process of purification of liquids. The mixture of two liquid hydrocarbons can be seperated by
using distillation under reduced pressure. The reduced pressure allows the mixture to boil at lower temperature
which prevent the degradation of hydrocarbon.
17. The reaction of toluene with Cl2 in presence of FeCl3 gives 'X' and reaction in presence of light gives 'Y'. Thus, 'X'
and 'Y' are [AIPMT (Prelims)-2010]
(1) X = Benzal chloride, Y = o-chlorotoluene
(2) X = m-chlorotoluene, Y = p-chlorotoluene
(3) X = o-and p-chlorotoluene, Y = Trichloromethyl benzene
(4) X = Benzyl chloride, Y = m-chlorotoluene
Sol. Answer (3)
CH3 CH3 CH3
Cl
FeCl3
(i) + Cl3 and
Cl x (O– and p-chlortoluene)
CH3 CCl3
hv
(ii) + Cl2
Y (Trichloromethyl benzene)
In reaction I, electrophilic substitution is taking place where as in reaction II, free radical substitution is taking
place. Therefore In reaction I, substitution took place in the ring whereas in
18. In the following the most stable conformation of n-butane is [AIPMT (Prelims)-2010]
CH3 CH3 CH 3
H H CH3
H CH3 H
CH3
(1) (2) (3) (4)

H H H H H
H
H CH3 H H H H H3C H
Sol. Answer (2)

The anti conformer of n-butane is the most stable conformation, In anti conformation, the distance between
the two –CH3 groups is maximum and repulsion between electron charge cloud is minimum stability.
19. Benzene reacts with CH3Cl in the presence of anhydrous AlCl3 to form [AIPMT (Prelims)-2009]
(1) Chlorobenzene (2) Benzylchloride (3) Xylene (4) Toluene
Sol. Answer (4)
CH3
AlCl3
+ CH3–Cl + HCl
Toluene
+
Mechanism CH3 – Cl + AlCl3  CH3 + AlCl4–
CH3 CH3
H –
+ + AlCl4
+ CH3 + AlCl3 + HCl
20. Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2SO4 in the mixture,
nitric acid acts as a/an [AIPMT (Prelims)-2009]
(1) Acid (2) Base (3) Catalyst (4) Reducing agent
Sol. Answer (2)
21. How many stereoisomers does the molecules have? CH3CH = CHCH2CHBrCH3 [AIPMT (Prelims)-2008]
(1) 2 (2) 4 (3) 6 (4) 8
Sol. Answer (2)
22. The order of decreasing reactivity towards an electrophilic reagent, for the following would be
a. Benzene b. Toluene c. Chlorobenzene d. Phenol
[AIPMT (Prelims)-2007]
(1) d > b > a > c (2) a > b > c > d (3) b > d > a > c (4) d > c > b > a
Sol. Answer (1)
Phenol is more reactive than toluene towards electrophilic substitution reaction because +R effect of the –OH
group dominates order +I effect of –CH3 group and also phenol and toluene are more reactive than benzene
towards electrophilic substitution reaction because –OH and –CH3 both group are electron donating group.
Chlorobenzene is least reactive because of the electron withdrawing –I effect of Cl group.
23. Predict the product C obtained in the following reaction
HΙ  C
CH3CH2 – C  CH + HCl  B  [AIPMT (Prelims)-2007]
l
(1) CH3CH2 – C – CH3 (2) CH3 – CH – CH2CH2l
Cl Cl
l l
(3) CH 3 – CH 2 – CH 2 – C – H (4) CH3 – CH2 – CH – CH2Cl

Cl
Sol. Answer (1)
Cl
+
H + Cl
–
CH3–CH2–C CH CH3–CH2–C=CH2 CH3–CH2–C=CH2
Vinyl carbocation
Cl Cl Cl
H
+
I
–
CH3–CH2–C=CH2 CH3–CH2–C–CH3
CH3–CH2–C=CH3
+
I
24. Which one of the following alkenes will react fastest with H2 under catalytic hydrogenation conditions ?
[AIPMT (Prelims)-2005]
R H R R R R R R
(1) (2) (3) (4)
R H R R H H R H
(R = Alkyl substituent)
Sol. Answer (1)
Lesser the stability of alkene, higher is rate of hydrogenation also less substituted alkenes undergo hydrogenation
faster because steric hundrance is less.
R R R R
and are highly substituted, so they will undergo hydrogenation slowly.
R H R R
R R R H
will undergo hydrogenation faster than because one end of R2C = CH2 contains
H H R H
two alkyl group and it will hinder the approach of hydrogen involved in the hydrogenation.
25. Which is maximum stable?
(1) But-1-ene (2) cis-but-2-ene (3) trans-but-2-ene (4) All have equal
Sol. Answer (3)
More substituted alkene are more stable among as and trans isomer, trans isomer is more stable due to less
steric hindrance. Hence trans-but-2ene is more stable than cis-but-2ene and but-1-ene which is less substituted.
26. Geometrical isomers differ in

(1) Position of functional group (2) Position of atoms
(3) Spatial arrangement of atoms (4) Length of carbon chain
Sol. Answer (3)
Geometrical isomer have same molecular formula but different spatial arrangement by atoms/groups.
a a a b
C=C C=C
b b b a
cis trans
27. The correct order of reactivity towards the electrophilic substitution of the compounds aniline (I), benzene (II)
and nitrobenzene (III) is
(1) III > II > I (2) II > III I (3) I < II > III (4) I > II > III
Sol. Answer (4)
Presence of electron donating group increases the reactivity of benzene towards electrophilic substitution while
electron withdrawing groups decreases the reactivity of benzene towards electrophilic substitution.
Among aniline (I), benzene (II) and nitrobenzene, aniline is most reactive because of the presence of electron
releasing –NH2 group while nitrobenzene is least reactive due to the presence of electron withdrawing –NO2 group.
NH2 NO2
> >
Aniline Benzene Nitrobenzene
28. The reactive species in the nitration of benzene is

(1) NO3 (2) NHO3 (3) NO2+ (4) NO2–
Sol. Answer (3)

HNO3 + H2SO4 HSO 4 + NO 2 + H2O
This NO2 ion acts as electrophile during the nitration of benzene.
29. H3C CH CH CH2 + HBr  A
CH3
A (predominantly) is
(1) CH3 CH CH CH3 (2) CH3 CH CH2 CH2Br
CH3 Br CH3
Br
(3) CH3 C CH2CH3 (4) CH3 CH CH CH3

CH3 Br CH3
Sol. Answer (3)
H Br
H
  1, 2 hydride
 Br
CH3–CH–CH=CH2 CH3 C CH–CH3 CH3 C CH2–CH3 CH3 C CH2 CH3 A
Shift
CH3 CH3 CH3 CH3
30. The alkene R–CH = CH2 reacts readily with B2H6 and the product on oxidation with alkaline hydrogen peroxides
produces
(1) R C O (2) R CH CH2 (3) R–CH2–CHO (4) R–CH2–CH2–OH
CH3 OH OH
Sol. Answer (4)
B2H6 H2O2,OH
R–CH=CH2 THF
R–CH2–CH2–BH2 R–CH 2–CH2–OH
This is hydroboration of alkene which results in anti Markovnikov's additon of water to the alkene.
31. Electrophile in the case of chlorination of benzene in the presence of FeCl3 is

(1) Cl (2) FeCl3 (3) Cl+ (4) Cl–
Sol. Answer (3)
+ – + –
Cl2+FeCl2 Cl–Cl……FeCl3 Cl + FeCl4
The Cl+ generated acts as electrophile during chlorination.
32. The bond length between central carbon atom and other carbon atom is minimum in
(1) Propene (2) Propyne (3) Propane (4) Pentane
Sol. Answer (2)
The C–C bond length is strotest when both carbon atoms are bonded with a triple bond. Since propyne contains
a triple bond, it has minimum C–C bond length.
33. Which of the following is used as an anti-knocking material?

(1) Glyoxal (2) Freon
(3) T.E.L. (4) Ethyl alcohol
Sol. Answer (3)
T.E.L. is tetraethyl lead which is used as anti knocking additive for petrol (C2H5)4Pb - T.E.L.
34. Which of the following reaction is expected to readily give a hydrocarbon product in good yields?
Cl
(1) CH3 CH3   C H OH
(2) (CH3 )3 CCl 2  
2 5

I2
(3) RCOOK   
Electrolysis
(4) RCOOAg 
h
Oxidation
Sol. Answer (3)

Electrolysis of sodium or pottasium salt of carboxylic acid gives hydrocarbon in good yield. This method is
known as kolbe's electrolytic method
Electrolysis
2 R-COOK + 2H2O   R-R + 2CO2 + H2 + 2KOH
CH2OH
35. In a reaction : CH2  CH2    M 
Hypochlorous R
, where M = Molecule and R = Reagent. M and R
acid
CH2OH
are
(1) CH3CH2OH and HCl (2) CH3–CH3 and heat
(3) CH3CH2Cl and NaOH (4) CH2Cl–CH2OH and aq. NaHCO3
Sol. Answer (4)

Cl OH OH
Hypochlorous acid Aq. Na2CO3
CH2 = CH2 CH2–CH2–OH CH2–CH2
HOCl
M R
36. The cylindrical shape of alkyne is due to

(1) Two sigma C–C and one  C–C bonds (2) One sigma C–C and two  C–C bonds
(3) Three sigma C–C bonds (4) Three  C–C bonds
Sol. Answer (2)
R – C  C – R (Alkyne)
The cylindrical shape of the alkyne is due to triple bond which consist of one sigma and two  bonds. The
electron cloud between two carbon atoms is cylindrically symmetrical about the internuclear axis.
37. In the commercial gasolines, the type of hydrocarbons which are more desirable is
(1) Linear unsaturated hydrocarbon (2) Toluene
(3) Branched hydrocarbon (4) Straight-chain hydrocarbon
Sol. Answer (3)
For commercial gasolines branched hydrocarbons are more desirable because they react more rapidly with
oxygen and undergo combustion easily.
38. The most stable conformation of n-butane is
(1) Gauche (2) Staggered (3) Skew boat (4) Eclipsed
Sol. Answer (2)
CH3 CH3 H
CH3
H
H
H H H H
H CH3
Eclipsed form of n-butane staggered form of n-butane
Staggered form of n-butane is more stable because of minimum repulsion between the electron charge clouds
of C–H bond due to maximum distance between the groups.
39. Which one of these is not compatible with arenes?

(1) Electrophilic additions (2) Delocalisation of -electrons
(3) Greater stability (4) Resonance
Sol. Answer (1)
Arenes are aromatic compound which are very stable due to their aromaticity. In arenes electrophilic substitution
is possible because substitution does not affect their aromaticity but addition will lead to disturbance of
aromaticity. Arenes show delocalization of -electron and are stable because of resonance but they will not
undergo electrophilic additions.
40. When acetylene is passed through dil. H2SO4 in the presence of HgSO4, the compound formed is
(1) Acetic acid (2) Ketone (3) Ether (4) Acetaldehyde
Sol. Answer (4)
2+
H
Hg
HC CH + H2O H2SO4
CH2 = C – OH CH3 – CHO
41. In Friedel-Craft’s alkylation, besides AlCl3 the other reactants are
(1) C6H6 + CH3Cl (2) C6H6 + CH4 (3) C6H6 + NH2 – NH2 (4) C6H6 + CH3COCl
Sol. Answer (1)
CH3
AlCl3
+ CH3Cl + AlCl3 + HCl
(C6H6)
Friedel craft's alkylation
42. Gammexane is
(1) Bromobenzene (2) Benzyl Chloride
(3) Chlorobenzene (4) Benzene hexachloride
Sol. Answer (4)
Cl
Cl Cl
Cl Cl
Cl
Benzene hexachloride (gammexane)
43. In Friedel-Crafts reaction, toluene can be prepared by
(1) C6H6 + CH3Cl (2) C6H5Cl + CH4 (3) C6H6 + CH2Cl2 (4) C6H6 + CH3COCl
Sol. Answer (1)
+ –
CH3–Cl + AlCl3 CH3 + AlCl4
+ CH3 CH3
AlCl4
+ CH3 + + AlCl3 + HCl
H
Toluene
44. 2-butene shows geometrical isomerism due to
(1) Restricted rotation about double bond (2) Free rotation about double bond
(3) Free rotation about single bond (4) Chiral carbon
Sol. Answer (1)
CH3 CH3 H CH3

C=C C=C
H H CH3 H
cis-but-2-ene trans-but-2-ene
In alkene geometrical isomerism is possible due to restricted rotation about the double bond. Due to this restricted
rotation, cis and trans form are not readily convertible into other and exist as pair of geometrical isomers.
45. Dihedral angle in staggered form of ethane is
(1) 0° (2) 120° (3) 60° (4) 180°
Sol. Answer (3)
H Dihedral angle (60°)
H H
H H
H
Staggered form of ethane
46. Which alkene on ozonolysis gives 'CH3CH2CHO and CH3CCH3 ?

||
O
CH3
(1) CH3CH2CH C
||
(2) CH3CH2CH = CHCH2CH3
CH3
(4) CH3 – C CHCH3
||
(3) CH3CH2CH = CHCH3
|
CH3
Sol. Answer (1)
CH3 O CH3
O3 Zn/H2O
CH3–CH2–CH=C CH3–CH2–CH C
CH3 CH3CH2CHO + CH3COCH3
CH3
O O
47. In preparation of alkene from alcohol using Al2O3 which is the effective factor?
(1) Porosity of Al2O3 (2) Temperature
(3) Concentration (4) Surface area of Al2O3
Sol. Answer (2)
Dehydration of alcohol in presence of Al2O3 gives alkene. Al2O3 acts as a catalyst and rate of the reaction of
affected by the temperature.
CH3
48. The compound CH3 C CH CH3 on reaction with NaIO4 in the presence of KMnO4 gives
(1) CH3COCH3 (2) CH3COCH3 + CH3COOH
(3) CH3COCH3 + CH3CHO (4) CH3CHO + CO2
Sol. Answer (2)
CH3
NaIO4 [O]
CH3 C CH CH3 CH3COCH3 + CH3CHO CH3COOH
KMnO 4
Initially CH3CHO is formed but since KMnO4 is a strong oxidizing agent, it oxidizes CH3CHO to CH3COOH.
Therefore products are CH3COCH3 and CH3COOH.
(i) O / ether
49. Products of the following reaction CH3 C  CCH2CH3  
3
  are
(ii) H2O / Zn
O O
(1) CH3 – C – C – CH2 – CH3 (2) CH3COOH + HOOC.CH2CH3
(3) CH3CHO + CH3CH2CHO (4) CH3COOH + CH3COCH3

Sol. Answer (1)
O O O
(i) O3/ether (ii) Zn/H2O
CH3–CC–CH2–CH3 CH3–C – C–CH2–CH3 CH3–C–C–CH2–CH3
O O
50. Which of the compounds with molecular formula C5H10 yields acetone on ozonolysis?
(1) 3-methylbut-1-ene (2) Cyclopentane (3) 2-methylbut-1-ene (4) 2-methylbut-2-ene
Sol. Answer (4)
CH3 CH3 O O
O3 Zn
CH3–C=CH–CH3 CH3–C – CH–CH3 H2O
CH3–C–CH3 + CH3–CHO
O O
Hence 2-methyl but-2-ene will give acetone on ozonolysis

51. One of the following which does not observe the anti-Markownikoff’s addition of HBr, is
(1) Pent-2-ene (2) Propene (3) But-2-ene (4) But-1-ene
Sol. Answer (3)
Br
CH 3–CH =CH–CH3 + HBr CH 3–CH 2–CH–CH 3
Symmetrical alkenes do not show anti-markovnikov's addition
52. Given
Br Br H Br
H H
CH3
and
CH3 CH3 CH3
H
Br
I II
I and II are
(1) A pair of optical isomers (2) Identical
(3) A pair of conformers (4) A pair of geometrical isomers
Sol. Answer (3)
Compound I and II are a pair of conformers. They are not geometrical isomers because they do not contain
double bond also not optical isomers because carbon-2 and 3 contain same groups. These are a pair of
conformers because they are redaily interconvertible into one another just by the rotation about C–C bond.
53. Which of the following conformers for ethylene glycol is most stable?
OH OH OH
OH H
H H
(1) (2) (3) (4)
H H H HO
H H H H
OH H H
Sol. Answer (4)
The gauche conformers of ethylene glycol is the most stable conformation because of intramolecular H-bonding
H
–H–bond
Gauche conformer
This type of hydogen bonding is possible only in gauche conformer. Therefore it is the most stable conformation
of ethylene glycol.
54. Reaction of HBr with propene in the presence of peroxide gives

(1) Isopropyl bromide (2) 3-bromo propane (3) Allyl bromide (4) n-propyl bromide
Sol. Answer (4)
peroxide
CH3 – CH = CH2 + HBr   CH3 – CH2 – CH2 – Br (n-propyl bromide)
In the presence of peroxide, addition of HBr to unsymmetrical alkene follows anti markovnikov's rule. Due to
the free radical addition. In presence of peroxide HBr dissociates into radicals.
55. Which one of the following is a free-radical substitution reaction?
CH3 Boiling CH2Cl Anh. AlCl3 CH3

(1) + Cl2 (2) + CH3Cl
CH2Cl CH2NO2
(3) + AgNO2 (4) CH3CHO + HCN  CH3CH(OH)CN
Sol. Answer (1)
Cl2 2Cl
CH3 CH2 CH2 CH2Cl
+ Cl + HCl + Cl2
Benzyl radical
56. Using anhydrous AlCl3 as catalyst, which one of the following reactions produces ethylbenzene (PhEt)?
(1) H3C – CH2OH + C6H6 (2) CH3 – CH = CH2 + C6H6
(3) H2C = CH2 + C6H6 (4) H3C – CH3 + C6H6
Sol. Answer (3)
AlCl3 
CH2 = CH2 + H+   CH2 – CH3
CH2–CH3 CH2–CH3
 –H
+
+ CH2 – CH3 
H
Ethyl benzene
57. Which of the following compounds undergoes nucleophilic substitution reaction most easily?
Cl
Cl
(1) (2)
OCH3
Cl
Cl
(3) (4)
NO2
CH3
Sol. Answer (3)
Benzene undergoes nucleophilic substitution reaction when a strong electron withdrawing groups are attached
to it. p-chloro nitrobenzene has one – Cl and – NO2 group which are electron withdrawing groups. Hence p-
chloronitrobenzene will undergo nucleophilic substitution because of the presence of – NO2 group which is a
strong electron withdrawing group due to its –I and –R effect.
58. Consider the reactions :
(i) (CH3 )2 CH  CH2Br

C H OH

2 5
 (CH3 )2 CH  CH2OC2H5  HBr
(ii) (CH3 )2 CH  CH2Br

C H O

2 5
 (CH3 )2 CH  CH2OC2H5  Br 
The mechanisms of reactions (i) and (ii) are respectively

(1) SN2 and SN2
(2) SN2 and SN1
(3) SN1 and SN2
(4) SN1 and SN1
Sol. Answer (1)
C2H5OH
(i) (CH3)2CH – CH2Br   (CH3)2CH – CH2 – OC2H5 + HBr
When the nucleophile is weak, reaction follows SN1 mechanism. Since C2H5OH is a weak nucleophile is
weak, reaction follows SN1 mechanism.
C H O–
(ii) (CH3)2CH – CH2Br 
2 5  (CH3)2CH – CH2 – OC2H5 + Br–
C2H5O– is a strong nucleophile because it is negatively charged. Therefore it will give SN2 reaction with
(CH3)2CH – CH2Br
59. Which will undergo fastest SN2 substitution reaction when treated with NaOH?
CH3 CH3
(1) H5C2 C Br (2) CH3 C Br
H CH3
CH3 H
(3) H C Br (4) H C CH2 — CH2 — CH3
C2H5 Br
Sol. Answer (4)

Reactivity of substrates towards SN2 reaction is in the order 1° > 2° > 3° This is due to steric hindrance which
is minimum in (1°) primary alkyl halides and maximum in (3°) tertiary alkyl halides. Br – CH2 – CH2CH2 – CH3
is a primary alkyl halide and it will undergo SN2 reaction fastest.
ether HCl
60. Given reaction Br Mg X H2O Y(main product) Y in the reaction is
(1) Hexane (2) Cyclohexane

(3) Cyclohexylcyclohexane (4) Cyclohexylether
Sol. Answer (2)
– +
ether HCl
Br Mg
MgBr H2O H + Mg(OH)Br
X Y(cyclohexane)
61. Monobromination of 2-methylbutane gives how many distinct isomers?

(1) One (2) Two (3) Three (4) Four
Sol. Answer (4)
Four isomers of 2-methyl butane is formed on monobromination. These are
CH3 CH3 CH3 CH3
CH3 C CH2 — CH2 — Br CH3 C CH — CH3 CH3 C CH2 — CH3 CH2 C CH2 — CH3
H (I) H (II) Br Br (III) Br H (IV)
62. When CH3CH2CHCl2 is treated with NaNH2, the product formed is

(1) CH3 – CH = CH2 (2) CH3 – C  CH
NH2 Cl
(3) CH 3CH 2CH (4) CH3CH2CH
NH2 NH2
Sol. Answer (2)
NaNH2
CH3 – CH2 – CHCl2  CH3 – C  CH
Vicinal dihalides undergo elimination in the presence of a strong base to give alkyne.
63. 2-Bromopentane is heated with potassium ethoxide in ethanol. The major product obtained is
(1) trans-pent-2-ene (2) Pent-1-ene (3) 2-ethoxypentane (4) cis-pent-2-ene
Sol. Answer (1)
Br Br
E2 CH3 H
CH3–CH–CH–CH2–CH3 CH3–CH – CH–CH2–CH3 Elimination C=C
H CH2– CH3
H H OC2H5 Trans-pent-2-ene
OC2H5
Anti elimination leads to the formation of trans product
64. An organic compound A(C 4H 9Cl) on reaction with Na/diethyl ether gives a hydrocarbon which on
monochlorination gives only one chloro derivative then, A is
(1) t-butly chloride (2) Secondary butyl chloride
(3) Iso butyl chloride (4) n-butyl chloride
Sol. Answer (1)
65. In the following reaction
1. Mg, Ether
C6H5 CH2Br  
 X,
2. H3O
the product ‘X’ is

(1) C6H5CH2OCH2C6H5 (2) C6H5CH2OH (3) C6H5CH3 (4) C6H5CH2CH2C6H5
Sol. Answer (3)
– +
CH2Br CH2 Mg Br CH3

Mg/Ether H3O
+ Mg(OH)Br
In the presence of acid, grignards reagent gives the corresponding alkane by abstraction proton from the acid.
66. When 3, 3-dimethyl 2-butanol is heated with H2SO4, the major product obtained is
(1) 2, 3-dimethyl 2-butene (2) cis and trans isomers of 2, 3-dimethyl 2-butene
(3) 2, 3-dimethyl 1-butene (4) 3, 3-dimethyl 1-butene
Sol. Answer (1)
CH3 CH3 CH3

H2SO4 –H2O  1, 2-methyl
CH3 C CH — CH3 CH3 C CH — CH3 CH3 C CH — CH3
shift

CH3 OH CH3 OH2 CH3
2º carbocation
CH3
 
–H
CH3 C C — CH3 CH3 C C — CH3
CH3 CH3 CH3

3°-carbocation 2,3-dimethyl 2-butene
This reaction is dehydration of alcohol which involves rearrangement.
67. Identify Z in the sequence of reaction
HBr
CH3 – CH2 –
CH CH2 
H O /h
Z
2 2
(1) CH3 CH2 CH CH3 (2) CH3 – CH2 – CH2 – CH2 – Br

Br
(3) CH3 CH CH CH2 (4) None of these

Br
Sol. Answer (2)

HBr
CH3 –CH2 – CH = CH2 
H O /hv
 CH – CH – CH – CH – Br
3 2 2 2
2 2
Addition of HBr to unsymmetrical alkene follow free radical mechanism and the addition is anti markovnikov's
addition.
CH3
H2O/H
68. In the following reaction : H3C–C–CH = CH2
CH3
A + B
Major Product Minor Product
The major product is
CH3 CH3
H3C–C – CH–CH3 H3C–C – CH2–CH2
(1) (2)
CH3 OH CH3 OH
CH3 CH3
H3C–C – CH–CH3 CH2–C–CH2–CH3
(3) (4)
OH CH3 OH CH3
Sol. Answer (3)
CH3 CH3 CH3


H  1,2-methyl 
CH3–C – CH=CH2 CH3–C – CH – CH3 shift CH3–C – CH – CH3
CH3 CH3 CH3

2° carbocation 3° carbocation
H2O H2O
CH3 CH3
CH3–C – CH–CH3 CH3–C – CH–CH3


CH3 OH2 OH2 CH3
 
–H –H
CH3 CH3
CH3–C – CH–CH3 CH3–C – CH–CH3
CH3 OH OH CH3
Tertiary (3°) carbocations are more stable than a secondary (2°) carbocation. Therefore rearrangement takes
place to give 3° carbocation and major product is formed from it.
69. What products are formed when the following compound is treated with Br2 in the presence of FeBr3?
CH3
CH3
CH3 CH3 CH3 CH3
Br Br Br
(1) and (2) and
CH3 CH3 CH3 CH3
Br
CH3 CH3 CH3 CH3

Br
(3) and (4) and
CH3 CH3 CH3 Br CH3

Br Br
Sol. Answer (3)
CH3 CH3 CH3

Br
Br2/FeBr3
+
Ortho and para directing
CH3 CH3
Br
SECTION - D
Assertion-Reason Type Questions
1. A : CHC–CH2–CH=CH2 adds up HBr to give CHC–CH2–CH–CH3 while CHC–CH=CH2 adds up HBr to give
|
Br
CH2=C–CH=CH2
|
Br
R : Double bond is always more reactive than triple bond towards electrophillic addition reaction.
Sol. Answer (3)
Alkenes are more reactive than alkynes and addition of electrophilic reagent takes place preferably at double
bond when both double and triple bond are present in the substrate. When electrophile add to alkyne, vinylic
cation is formed which is highly unstable on the other hand addition of electrophile to alkene forms alkyl radicals
which are more stable vinyl cations. Therefore alkenes are more reaction.
Hence assertion is true but reason is false.
2. A : In alkene, hydroboration oxidation process is an example of pericyclic reaction.
R : BH3 forms the cyclic transition state with double bond.
Sol. Answer (1)
The hydroboration of alkene is an example of pericyclic reaction. Pericyclic reactions are concerted reaction
wich proceeds through cyclic transition state.
Therefore both assertion and reason are true.
CH3
|
3. A : When isobutane is reacted with Cl2 in presence of sunlight then CH3–CH–CH2Cl is formed in high
percentage.
R : The reactivity of 1°, 2° & 3° H-atoms towards chlorine are 1 : 3.8 : 5 respectively.
Sol. Answer (2)
Assertion is true because ratio of selectivity for 3° carbon to 1° carbon is 5:1
Total selectivity for 1° carbon for 1° carbon = 9 × 1 = 9
Total selectivity for 3° carbon = 5 × 1 = 5
Hence reason is also true but not the correct explanation of assertion.
4. A : On dehydration with concentrated H2SO4, neopentyl alcohol gives 2-methyl butene-2.

R : 3° carbocation is more stable than 2° carbocation.
Sol. Answer (2)
CH3 CH3 CH3

H

 –H2O 
1,2-methyl
CH3–C – CH2–OH CH3–C – CH2 – OH2 CH3–C – CH2
shift
CH3 CH3 CH3

 –H
CH3–C – CH2 – CH3 CH3–C = CH – CH3
CH3 CH3
Assertion is true because neopentyl alcohol gives 2-methyl but-2ene on dehydration and reason is also true
that 3°carbocation is more than 2° carbocation but is is not the correct explanation of assertion.
5. A : Generally, n-hexane and onwards can be sulphonated but isobutane and isopentane can also be
sulphonated.
R : Isobutane and isopentane can produce tertiary free radical.
Sol. Answer (1)
n-hexane, isobutane and isopentane can be sulphonated. Isobutane and isopentane forms tertiary radicals and
tertiary radicals are stable. Since these compound gives stable inter mediate they can undergo sulphonation.
Hence both assertion and reason are true and reson is the correct explanation of assertion.
6. A : When 2-fluorobutane is reacted with alcoholic KOH then butene-1 is formed as major product.
R : Butene-2 is more stable than butene-1.
Sol. Answer (2)
When 2-fluorobutane is reacted with alcoholic KOH 1-butane is formed as major product because presence
of fluorine stabilizes the intermediate which lead to formation of less substituted alkene
F F
– –
CH3 – CH2 – CH – CH2 CH3 – CH – CH – CH3
– –
(I) H H OC2H5
OC2H5
(II)
7. A : When butyne-2 is reacted with Na/liq. NH3 then trans-butene-2 is formed.
R : This reaction proceeds through free radical intermediate.
Sol. Answer (2)
Assertion is true that reduction of 2-butyne with Na/Liq. NH3 gives trans-2-butene as reduction of alkyne with
Na/liq NH3 gives trans alkene.
Reason is also that reduction with Na/liq NH3 follows free radical mechanism but reason is not the correct
explanation of assertion.
8. A: has 12  electrons i.e. 4n  electrons.
R : It is an antiaromatic compound.
Sol. Answer (3)
Assertion is true because the two benzene ring totally contains 12 electrons but the compound is not anti
aromatic because both ring are joined by a double bond and aromaticity is maintained individually by each
ring having 6 electron (4n + 2) electrons. So reason is false
9. A : Propene reacts with HBr in presence of H2O2 gives 2-bromopropane as a major product.
R : This reaction proceeds always through 2° free radical as intermediate.
Sol. Answer (3)
The addition of HBr to propene in presence of H2O2 gives 2-bromopropane as major product. Hence assertion
is true. This addition takes place through the formation of 1° radical, so reason is false.
CH3 – CH = CH2 + Br CH3 – CH – CH2

Br 1º radical
CH3 – CH – CH2 + HBr CH 3 – CH – CH 3 + Br

Br Br
10. A : Boiling point of n-pentane is more than neopentane but the melting point of neopentane is more than n-
pentane.
R : Branching decreases the boiling point but increases the melting point.
Sol. Answer (3)
Boiling point of a hydrocarbon depend on the magnitude of van der Waals forces which is maximum for linear
hydrocarbons so n-pentane has higher B.P. than neopentane but melting point depend on the packing of the
constituent molecules and more spherical molecules are more tightly packed. Since neopentane is spherical
shaped due to branching, it has higher melting point then n-pentane.
11. A : Alkynes is more reactive than alkene towards electrophilic addition reaction.
R : Alkynes form stable carbocation than alkene.
Sol. Answer (4)
Alkynes are less reactive than alkenes because addition of electrophile to alkyne gives vinyl cation which is
unstable while additon of electrophile to alkene give alkyl carbocation which is more stable than vinylcation.
So assertion is false reason is also false because alkene gives alkyl carbocation which is more stable than
vinylcation.
Hence reason is also false.
12. A : on reaction with Na/NH3 gives as major product.
R : This reaction occurs through the formation of carbocation intermediate.

Sol. Answer (3)
The product of the reaction of benzene with Na/liq. NH3 gives 1,4-cyclohexadiene.
Na/liqNH3
This reaction does not involve the formation of carbocation, as this reaction follows free radical mechanism.
Therefore assertion is true, reason is false.
13. A : But-1-yne has acidic hydrogen but but-2-yne does not.
R : In but-1-yne hydrogen atom is attached with sp hybridised carbon but no hydrogen is attached with sp
hybridised carbon in but-2-yne.
Sol. Answer (1)
In but-2-yne both the sp hybridized carbon which are electronegative, they are attached to methyl group while
in but-1-yne the terminal sp hybridized carbon is attached to a hydrogen which can be released due to the
high electronegativity of sp hybridized carbon.
– +
CH3 – C  C – CH3 CH3 – CH2 – C  C – H
But-2-yne But-1-yne
Therefore both assertion and reason are true and reason is correct explanation of assertion.
14. A : CH3 CH2 CH CH3 on reaction with KNH2 gives but-1-ene as major product.
F
R : It follows E1CB mechanism.
Sol. Answer (1)
When a highly electron withdrawing group is attached with alkyl group, elimination reaction proceeds through
the formation of stable carbanion as intermediate.
F F F
Na/NH2
CH3 – CH2 – CH – CH3 CH3 – CH – CH – CH3 and CH3 – CH2 – CH – CH2
(I) (II)
Since II is more stable carbanion,elimination from II will give but 1-ene. This reaction gollows E1CB mechanism
because it involves formation of carbanion as intermediate. Hence both assertion and reason are true.
15. A : Methane cannot be prepared by kolbe electrolytic reaction.

R : In this reaction alkane is liberated at anode.
Sol. Answer (2)
Methane cannot be prepared by kolbe's electrolytic method because the alkane formed in kolbe's electrolytic
method contains even number of carbon atom due to combination of alkyl radicals. The alkane formed is
liberated at anode during the reaction.
Hence assertion and reason are true but reason is not the correct explanation of assertion.
16. A : Benzene on reaction with V2O5 gives maleic anhydride at high temperature.
R : V2O5 act as reducing agent.
Sol. Answer (3)
Benzene on oxidation with V2O5 gives maleic anhydride at high temperature
O
V2O5 CH2 C
O
CH2 C
moleic anhydride O
V2O5 acts as oxidizing agent. Assertion is true but reason is false.
17. A : The rate of sulphonation of benzene and deutrobenzene is different in the presence of oleum.
R : The slow step is the breaking of C—H or C—D bond.
Sol. Answer (1)
In sulphonation of benzene and deuterobenzene, C–H and C–D bond are broken respectively. The rate of a
reaction depend on the slowest step and in sulphonation of benzene and deuterobenzene, breaking of C–H
and –C–D bond is the slow step and hence rate of reaction is different for both benzene and deuterobenzene.
18. A : Friedel-crafts alkylation of benzene occurs in the presence of Lewis acid.
R : The function of Lewis acid to generate electrophile.
Sol. Answer (1)
During the alkylation of benzene through friedel craft's reaction the lewis acid reacts with the alkyl halide and
generates electrophile CH3 – Cl + AlCl3  CH3 + AlCl4–
AlCl3 is a lewis acid and CH3 is the electrophile.
19. A : The reaction between benzene and (CH3)3C  COCl in the presence of anhyd AlCl3 gives ter-butyl benzene
as major product.
+ +
R : (CH3)3C  CO is formed first which converted into more stable (CH3)3C by liberating CO.
Sol. Answer (1)
O O
(CH3)3C – C – Cl + AlCl3 (CH3)3C – C + AlCl4
O CH3
(CH3)3C – C CH3– C + CO
CH3
CH3
CH3
C – CH3
+ CH3 – C
CH3
CH3
ber-butylbenzene
O O
(CH3)3C – C carbocation is not as stable as ter-carbocation therefore (CH3)3C – C eliminates CO to form
more stable 3° carbocation.

20. A : Addition of Br2 in trans-but-2-ene in the presence of CCl4 gives meso form.
R : The reaction occurs through anti addition.
Sol. Answer (1)
Trans-but-2-ene on undergoes anti addition of bromine to gives meso compound. Addition of bromine to alkene
first form cyclic bromonium ion and then backside attack of Br takes place and thus anti addition results
in the formation of meso product
Br
C–C

– C – Br
Br Br – C –
Meso product
21. A : Cyclohexane is more stable than cyclopentane.
R : According to Baeyer strain theory angle strain in cyclohexane is more than cyclopentane.
Sol. Answer (2)
According to baeyer strain theory angle strain is more in cyclohexane than cyclopentane but cyclohexane
is more stable than cyclopentane because cyclohexane ring is puckered in which all the angles are tetrahedral
hence stable.
22. A : Addition of HBr in buta-1, 3-diene gives 3-bromo-but-1-ene as major product at low temperature.
R : Addition of HBr in buta-1, 3-diene gives 1-bromo-but-2-ene as major product at high temperature.
Sol. Answer (2)
Addition of HBr to 1, 3-butadiene gives 3-bromo-but-1-ene as major product at low temperature because at low
temperature this reaction follows electrophilic additon but higher temperature HBr dissociates to form free radical
and 1-bromo-but-2-ene is formed as major product due to allylic delocalization.
23. A : Gauch conformer of ethylene glycol is most stable.

R : It is due to the formation of intramolecular hydrogen bonding.
Sol. Answer (1)
Gauch conformers of ethylene glycol is mor stable than other conformations due to intramolecular hydrogen
bonding
24. A : But-2-ene is more stable than propene.

R : Heat of hydrogenation of but-2-ene is lesser than that of propene.
Sol. Answer (1)
Lesser the heat of hydrogenation of an alkene, more is the stability heat of hydrogenation of but-2-ene is lesser
than that of propane. Hence but-2-ene is more stable.
25. A : Grignard reagent on reaction with alcohol form alkane.

R : Alcohol has acidic (active) hydrogen.
Sol. Answer (1)
Grignards reagent acts as a base and abstracts a proton from a species containing acidic hydrogen to give
– +
alkane CH3CH2MgBr + C2H5OH CH3CH2–H + MgBr (OC2H5) . The alcohol can acts as an acid due to
the polarity of O–H bond.


CLS Aipmt 17 18 XI Che Study Package 4 SET 2 Chapter 13

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CLS Aipmt 17 18 XI Che Study Package 4 SET 2 Chapter 13

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Chapter 13

2. Eclipsed form of ethane has higher energy due to

3. The angle strain in cyclopentane is

4. Which one is most stable?

Sol. Answer (4)

(1) – Anti-aromatic (2) – Anti-aromatic

(3) – Non-aromatic (4) – Aromatic

The possible compound A is

11. Which one is not prepared by Wurtz reaction?

Br + 2Na + CH3CH2Br 

(1) Compound C is CH3 – C  C – CH3 (2) C gives positive Tollen's test

Sol. Answer (2)

14. In the following compounds the decreasing order of B.P. is

(1) CH3 – CH – CH – CH3 (2) CH3 – C – CH2 – CH3

(3) CH3 – CH – CH2 – CH2Cl (4) CH3 – C – CH2 – CH3

17. In iodination ; for preparation of iodomethane compound used is

19. In which alkane isomerization will not occur?

(1) (2) (3) (4)

Sol. Answer (2)

The minimum heat of hydrogenation is in

(1) A (2) B (3) Both have equal (4) Cannot predict

Na/liq. NH3 CH3 H

CH2 CH2Br CH2Br

Sol. Answer (2)

CH2 CH3 CH3 CH3

23. In which of the following reactions Markovnikov’s rule is not observed ?

(4) Both (2) & (3)

26. What is X in the following sequence of reactions?

27. Addition of HBr to propene

(ii) CH3Br + 2Na + CH3CH2Br  CH3CH2CH3 + 2NaBr

29. Addition of HBr to 2-methyl-1-propene in the presence of hydrogen-peroxide produces

(1) Benzaldehyde (2) Toluene (3) Benzoic acid (4) Ethylbenzene

Oxidation CH–COOH  CH–C

33. In Kharasch effect; reaction follows

CH3– CH =CH 2+Br CH3–CH– CH2–Br+HBr CH3–CH2–CH2––Br+Br

Sol. Answer (1)

Hydrobaration oxidation results in the anti-Markownikov's additon of water to alkene.

(1) CH3 – CH = CH – CH3 (2) CH2 = CH – CH2 – CH3

Sol. Answer (2)

36. C KMnO4 + H2SO4 NaOH ;

CH2 Turns CuSO 4

Compound A , B and C are respectively

(1) CH2O, H2O and (2) , CO2, H2O

Which one is not A , B , C ?

Hence CH3CHO is not formed.

40. Baeyer’s reagent is

41. Acetylene when oxidized with chromic acid gives

Sol. Answer (4)

42. The catalyst used to reduce an alkyne to alkene is

S2Cl2+2 C2H 4Cl–CH2–CH2–S –CH2–CH2–Cl+S

47. Monomer of neoprene is

Sol. Answer (4)

50. In sulphonation of benzene; electrophilic reagent used is

51. Which one is o, p-directing group for electrophilic substitution reaction?

52. In Chlorobenzene, 2,4-dinitrochlorobenzene ,

The decreasing order of reactivity towards electrophilic substitution reaction is

(3) CH3 – C – CH2 – CH3 (4) CH3 – C – CH2I

Sol. Answer (2)

54. The electrophile which attacks in Friedel-Craft acylation is

55. Which of the following shows geometrical isomerism?

CH3 CH3 CH3 H

The best suitable reagent 'A' is

The most suitable reagent for given conversion is

3. Consider the following two structures