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CLS Aipmt-19-20 XIII Che Study-Package-3 Level-1 Chapter-15 PDF
CLS Aipmt-19-20 XIII Che Study-Package-3 Level-1 Chapter-15 PDF
Hydrocarbons
Solutions
SECTION - A
Objective Type Questions
1. The difference in potential energy between eclipsed and staggered form of ethane is
(1) Zero kJ/mol (2) 12.5 kJ/mol
(3) 22 kJ/mol (4) 44 kJ/mol
Sol. Answer (2)
In alkanes, C–C single bond rotation is hindered by a small energy barrier of 1-20 kJ mol–1 due to torsional
strain.
sp3
(Hence, 109° 28)
10928 109.5
Angle strain =
2 2
⎛ 360 ⎞
Where, 180 ⎜ ⎟
⎝ 5 ⎠
3 3
Angle strain = 0.75° = 1 60 45
4 4
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34 Hydrocarbons Solutions of Assignment
(1) (2)
(3) (4)
is antiaromatic compound (4e–)
(1) – Antiaromatic
(2) – Aromatic
N
H
(3) – Non-aromatic
(4) – Aromatic
6. Which one of the following statements 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)
Sigma-bond is stronger than pi-bond.
Bond energy (sigma) > Bond energy (pi)
Hence, option (2) is incorrect.
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Solutions of Assignment Hydrocarbons 35
CH3
7. A + NaOH CH3 – C – CH2 – CH3 ;
(CaO)
(Soda lime) H
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)
CH3 CH3
Soda lime
CH3 – C – CH2 – CH2 – COONa CH3 – C – CH2 – CH3
H H
CH3 CH3
Soda lime
CH3 – CH2 – CH – CH2 – COONa CH3 – CH2 – C – CH3
H
CH3 CH3
Soda lime
CH3 – C – CH2COONa CH3 – C – CH3
H H
8. On electrolysis of sodium succinate the alkene obtained is ______ and nature of solution after electrolysis is
______
CH3 CH3
(3) CH4 (4) CH 3 – CH – CH – CH 3
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36 Hydrocarbons Solutions of Assignment
CH3 CH3
| |
10. In CH3–C–OH, CH3–CH–OH, CH3–CH2–CH2OH
|
CH3
(I) (II) (III)
The ease of rate of dehydration is
(1) (I) > (II) > (III) (2) (II) > (I) > (III) (3) (III) > (II) > (I) (4) (I) > (III) > (II)
Sol. Answer (1)
More the stability of carbocation formed, easier will be the dehydration of Alcohol.
Stability of carbocation : 3° > 2° > 1°
CH2CH3
(1) Wurtz reaction (2) Fittig reaction (3) Wurtz fittig reaction (4) Frankland reaction
Sol. Answer (3)
Wurtz Fittig reaction
Dry ether
Cl + 2Na + Cl – CH2 – CH3 CH2 – CH3 + 2NaCl
Na CH3Br
12. Mg2C3 + H2O A B C ;
The incorrect statement for C is
(1) Compound "C" is CH3 – C C – CH3 (2) "C" gives positive Tollens test
(3) In compound "C" all four C are linearly present (4) Compound "C" on ozonolysis gives diketone
Sol. Answer (2)
Na
Mg2C3 + H2O CH3 – C CH CH3 – C C Na
Propyne B
A
CH3Br
O O
(i) O3 + CHCl3
CH3 – C – C – CH3 (ii) Zn + H2O
CH3 – C C – CH3
diketone But-2-yne
C
CH3
Cl2
CH3 – CH – CH2 – CH3 UV light
Cr2O3
CH3 – (CH2)4 – CH3 + 3H2
n-hexane
Benzene
18. A mixture of ethyl iodide and n-propyl iodide is subjected to Wurtz reaction. The hydrocarbon which will not
be formed is
(1) Butane (2) Propane (3) Pentane (4) Hexane
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38 Hydrocarbons Solutions of Assignment
Dry ether
C3H7 I 2Na I C3H7
C3H7 C3H7 2NaI
Hexane
Dry ether
C3H7 I 2Na I C2H5
C3H7 C2H5 2NaI
Pentane
19. Indicate the expected structure of the organic product when ethyl magnesium bromide is treated with heavy
water (D2O)
(1) C2H5–C2H5 (2) C2H5OD (3) Sodium benzoate (4) C2H5D
Sol. Answer (4)
CH4 I2 CH3 I HI
Iodomethane
21. In chlorination, the relative rate of abstraction of H in 3°, 2° and 1° H atom respectively is
(1) 5 : 3.8 : 2 (2) 5 : 3.8 : 1 (3) 1600 : 82 : 1 (4) 1600 : 5 : 82
Sol. Answer (2)
In chlorination 1 2 3
Relative rate 1 : 3.8 : 5
OH
H3PO4
22. In "A" ; Compound "A" is
Major
CH2 O
23. When butyne-2 is reacted with Na in liquid ammonia in presence of C2H5OH then the major product formed
is
(1) Cis-butene-2 (2) Trans-butene-2 (3) Butene-1 (4) No reaction
Sol. Answer (2)
Na in liq. NH3 CH3 H
CH3 – C C – CH3 C=C
butyne-2 H CH3
Trans-butene-2
(Major)
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Solutions of Assignment Hydrocarbons 39
Na/liq. NH3
25. CH3 – C C – CH3 A ;
Pd/CaCO3
B ;
(CH3COO)2Pb
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40 Hydrocarbons Solutions of Assignment
28. C6H5CH2CH2CH3 is when oxidised in the presence of alk. KMnO4, the product obtained is
(1) C6H5CHO (2) C6H5COOH (3) C6H5CH2CH2CHO (4) None of these
Sol. Answer (2)
C6H5CH2CH2CH3
alk. KMnO 4
[O]
C6H5 COOH
benzoic acid
29. 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 reactions, how many grams of propane will be
obtained?
44
(1) 44 g (2) 22 g (3) 33 g (4) g
3
Sol. Answer (4)
1 ⎛ 1 ⎞ 44
Mol of propane = w (propane) = ⎜ 44 ⎟ g
3 ⎝ 3⎠ 3
CH3 CH3
H2O2
CH3 – C = CH2 + HBr CH3 – C – CH3
2-methyl-1-propene
Br
2-bromo-2-methylpropane
K2Cr2O7
31. C6H5CH3
H2SO4
Y . Here Y is
32. C 6H6
Oxidation
X . Here, X is
V2O 5 /
(1) Maleic anhydride (2) Acetic acid (3) Propanoic acid (4) Succinic acid
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Solutions of Assignment Hydrocarbons 41
Sol. Answer (1)
O
V2O5, CH – C
O
oxidation CH – C
(C6H6)
O
(Maleic anhydride)
(1) B2H6
33. "A" . "A" is
(2) H2O2/OH (Major)
OH
OH
(1) (2) OH (3) (4)
OH
Sol. Answer (1)
(i) B2H6
(ii) H2O2/OH–
OH
(Major)
In HBO reaction, addition of H2O take place according to Antimarkonikov's rule.
CH3
C KMnO4 + H2SO4 NaOH
34. A B ; Compound B is
CH CaO
Milky Blue
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42 Hydrocarbons Solutions of Assignment
CH3
CH3 (1) O3
36. C = C – CH = CH2 A + B + C;
CH3 (2) Zn/H2O
O O
(1) CH 3 – C – CH 3 (2) CH2O (3) CH 3 – C – CHO (4) CH3CHO
CH3
CH3 (1) O3
37. A + B + C ;
(2) Zn/H2O
A, B, C is/are
O O O
CHO
(1) CH3 – C – C – CH3 (2) (3) CH 3 – C – CHO (4) All of these
CHO
Sol. Answer (4)
CH3
CH3 CH3
(1) O3 C=O CHO
2 +
(2) Zn/H2O CHO CHO
CH3
CH3 CH3
(1) O3 C=O CHO
+2
(2) Zn/H2O C=O CHO
CH3
CH CH
H2CrO 4
[O]
CH3 COOH
acetic acid
40. 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 prefers to restore aromaticity.
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Solutions of Assignment Hydrocarbons 43
41. Ethylene + S2Cl2 "A". The compound "A" is
(1) Lewisite (2) Mustard oil (3) Mustard gas (4) Insecticide
Sol. Answer (3)
CH2 = CH2 CH2 – CH2 – Cl
+ S2Cl2 S +S
CH2 = CH2 CH2 – CH2 – Cl
(Mustard gas)
2+ +
Hg , H
42. Ph – C CH + H2O "A" . The reaction is an example of
(1) Electrophilic addition (2) Nucleophilic addition
(3) Free radical addition (4) Electrophilic substitution
Sol. Answer (2)
In first step, Hg2+ adds to alkyne. Second step, H2O (nucleophile) attacks and adds to intermediate. Since
Hg2+ leaves as catalyst, hence, classification of nucleophilic addition reaction is more appropriate.
+
H
43. + CH3 – CH = CH2 A . Compound "A" is
O
(1) SO3H (2) SO3 (3) O = S = O (4) SO2OH
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44 Hydrocarbons Solutions of Assignment
O O
CH3
(1) – C – OH (2) – C – NH2 (3) – N (4) – NO2
CH3
Sol. Answer (3)
CH3
Due to +M effect of – N group.
CH3
UV
47. Benzene Cl2
500 K
A , A is
Cl
Cl Cl
UV
+ 3Cl2 500 K
Cl Cl
Cl
Benzene hexachloride (BHC)
or
Gammaxane
HI
48. 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
H+ I–
CH3 – CH = CH – CH2 – CH3 CH3 – CH – CH2 – CH2 – CH3 CH3 – CH – CH2 – CH2 – CH3
(More stable)
I
(Major)
O
–
O O
(1) R – C
–
(2) R – C (3) R – C – O (4) Both (1) & (3)
+
O O
anhy. AlCl3
R – C – Cl R – C + AlCl4
(Electrophile)
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Solutions of Assignment Hydrocarbons 45
50. 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 H CH3 H
C C
and
C C
H CH3 CH3 H
trans-but-2-ene cis-but-2-ene
SECTION - B
Previous Years Questions
1. In the following reaction,
red hot
H3C – C CH
iron tube
873 K
A, the
HC H
CH3 C – CH3 H3C
C Red Hot CH3
Iron tube
CH 873 K
CH H H
C
CH3
CH3
Number of
bonds = 21
H3C CH3
H3C C C CH3
H H
cis-2-butene
[NEET-2019]
(1) Na/liquid NH3
(2) H2, Pd/C, quinoline
(3) Zn/HCl
(4) Hg2+/H+, H2O
Sol. Answer (2)
H3C CH3
H2, Pd/C,
H3C C C CH3 C C
quinoline
H H
cis-2-butene
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46 Hydrocarbons Solutions of Assignment
3. Among the following, the reaction that proceeds through an electrophilic substitution, is [NEET-2019]
+ –
Cu 2Cl2
(1) N2CI CI + N2
AlCl 3
(2) + Cl2 CI + HCl
CI CI
UV light
(3) + Cl2 CI CI
CI CI
(4) heat
CH 2OH + HCl CH 2Cl + H2O
Cl
AlCl 3
+ Cl2 + HCl
Generation of electrophile:
.. + –
Cl Cl
.. + AlCl3 Cl Cl AlCl3
..
.. + –
Cl
.. + AlCl4
..
Electrophile
Cl H
+
Cl +
(i) etc
Cl Cl
H
+
(ii)
4. An alkene "A" on reaction with O3 and Zn–H2O gives propanone and ethanal in equimolar ratio. Addition of
HCl to alkene "A" gives "B" as the major product. The structure of product "B" is [NEET-2019]
CH3 Cl Cl CH3
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Solutions of Assignment Hydrocarbons 47
Sol. Answer (3)
CH3 CH3
O3
C CH CH3 C O+ O CH CH3
Zn/H2O
(A) Ethanal
CH3 CH3
Propanone
HCl
CH3
C CH2 CH3
CH3 Cl
(B)
5. Hydrocarbon (A) reacts with bromine by substitution to form an alkyl bromide which by Wurtz reaction is
converted to gaseous hydrocarbon containing less than four carbon atoms. (A) is [NEET-2018]
(1) CH CH (2) CH2 CH2
(3) CH4 (4) CH3 – CH3
Sol. Answer (3)
Na/dry ether
Br2/h Wurtz reaction
CH4 CH3Br CH3 — CH3
(A)
3Cl2 Br2 Zn
Fe HCl
Br Br
(C7H8) (A) (B) (C)
7. Which of the following molecules represents the order of hybridisation sp2, sp2, sp, sp from left to right atoms?
[NEET-2018]
(1) HC C – C CH (2) CH2 = CH – C CH
(3) CH3 – CH = CH – CH3 (4) CH2 = CH – CH = CH2
Sol. Answer (2)
sp2 sp2 sp sp
CH2 CH – C CH
Number of orbital require in hybridization = Number of -bonds around each carbon atom.
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48 Hydrocarbons Solutions of Assignment
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
O OH O
OH O
H2O, H2SO4 Tautomerism
H3C – C CH H3C – C = CH CH3 – C – CH3
HgSO4
(A) (B)
10. 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.
11. 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
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Solutions of Assignment Hydrocarbons 49
12. 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
13. In the given reaction + P, the product P is [NEET(Phase-2)-2016]
0°C
F F
(1) (2) (3) (4)
HF
–H
14. 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.
15. 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
16. 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
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50 Hydrocarbons Solutions of Assignment
17. 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.
18. 2,3-Dimethyl-2-butene can be prepared by heating which of the following compounds with a strong acid?
[Re-AIPMT-2015]
(1) (CH3)2C = CH – CH2 – CH3 (2) (CH3)2CH – CH2 – CH = CH2
CH3 CH3
+
H +
CH3 – C – CH = CH2 CH3 – C – CH = CH2 (2° carbocation)
CH3 CH3 H
1, 2 – methyl shift
CH3 CH3
+
–H +
CH3 – C = C – CH3 CH3 – C – C – CH3 (3° carbocation;
more stable)
CH3 CH3 H
(2, 3 – Dimethyl-2-butene)
19. 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
Cl
HCl
AlC to M.R.
CH3 CH3
Cl
HCl
AlC to M.R.
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Solutions of Assignment Hydrocarbons 51
20. A single compound of the structure
CH3 CH3
OHC C C
H
C C O
H2 H2
H
Or
CH3 CH3 CH3 CH3
O3/Zn O CH3 CH3
O or OHC CH2 CH C O
CH = CHCH3
Br
Br
Br
Sol. Answer (2)
HBr + –
C6H5 CH CH CH3 C6H5 CH CH CH3
HBr
Br
22. 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)
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52 Hydrocarbons Solutions of Assignment
23. Some meta-directing substituents in aromatic substitution are given. Which one is most deactivating?
[NEET-2013]
(1) –SO3H (2) –COOH (3) –NO2 (4) –CN
Sol. Answer (3)
–NO2 group is the most deactivating group in aromatic substitution among the given options. Both N and O
are electron withdrawing elements and –NO2 shows –R effect.
24. Which of the following compounds will not undergo Friedal-Craft's reaction easily? [NEET-2013]
(1) Xylene (2) Nitrobenzene (3) Toluene (4) Cumene
Sol. Answer (2)
Friedel-Craft's reaction is an example of electrophilic substitution. Electron withdrawing group present on
benzene ring decreases the electron density over benzene ring and decreases the reactivity towards electrophilic
substitution. –NO2 group is an electron withdrawing substituent and hence it will deactivate benzene ring towards
Friedel-Craft's reaction.
25. Among the following compounds the one that is most reactive towards electrophilic nitration is
[AIPMT (Prelims)-2012]
(1) Toluene (2) Benzene (3) Benzoic acid (4) Nitrobenzene
Sol. Answer (1)
In toluene –CH3 is attached with benzene ring which increases the electron density over benzene ring due to
hyper-conjugation and +I effect. This makes benzene ring more reactive towards electrophilic substitution.
(–NO2) nitro and – (COOH) carboxylic acid group are electron withdrawing group and they will deactivate
benzene ring towards electrophilic nitration.
26. 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)
27. Which one of the following is most reactive towards electrophillic reagent? [AIPMT (Prelims)-2011]
28. 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
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Solutions of Assignment Hydrocarbons 53
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.
29. 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
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
30. 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
31. 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
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54 Hydrocarbons Solutions of Assignment
32. 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)
33. Which one of the following is most reactive towards electrophilic attack? [AIPMT (Prelims)-2008]
Cl
CH2OH NO2 OH
(1) (2) (3) (4)
34. 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.
35. 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
–
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
36. 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)
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Solutions of Assignment Hydrocarbons 55
Sol. Answer (3)
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.
37. 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.
39. 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
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56 Hydrocarbons Solutions of Assignment
CH3
A (predominantly) is
(1) CH3 CH CH CH3 (2) CH3 CH CH2 CH2Br
CH3 Br CH3
Br
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
42. The alkene R–CH = CH2 reacts readily with B2H6 and the product on oxidation with alkaline hydrogen peroxides
produces
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.
44. 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.
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46. Which of the following reaction is expected to readily give a hydrocarbon product in good yields?
Cl C H OH
(1) CH3CH3
2
(2) (CH3 )3 CCl 2
5
h
I2
(3) RCOOK
Electrolys is
(4) RCOOAg
Oxidation h
CH2OH
47. In a reaction : CH2 CH2 M
Hypochloro us 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
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.
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58 Hydrocarbons Solutions of Assignment
52. 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 tautomerise
HC CH + H2O H2SO4
CH2 = C – OH CH3 – CHO
CH3
AlCl3
+ CH3Cl + AlCl3 + HCl
(C6H6)
Friedel craft's alkylation
54. Gammexane is
(1) Bromobenzene (2) Benzyl Chloride
(3) Chlorobenzene (4) Benzene hexachloride
Sol. Answer (4)
Cl
Cl Cl
Cl Cl
Cl
Benzene hexachloride (gammexane)
55. 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
56. 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
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Solutions of Assignment Hydrocarbons 59
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.
57. 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
CH3
(1) CH3CH2CH C
||
59. 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
60. 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
KMnO4
Initially CH3CHO is formed but since KMnO4 is a strong oxidizing agent, it oxidizes CH3CHO to CH3COOH.
Therefore products are CH3COCH3 and CH3COOH.
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60 Hydrocarbons Solutions of Assignment
(i) O / ether
61. Products of the following reaction CH3 C CCH2 CH3
3
are
(ii) H2 O / Zn
O O
62. 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 H2 O
CH3–C–CH3 + CH3–CHO
O O
OH OH OH
OH H
H H
(1) (2) (3) (4)
H H H HO
H H H H
OH H H
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Solutions of Assignment Hydrocarbons 61
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.
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.
CH2Cl CH2NO2
(3) + AgNO2 (4) CH3CHO + HCN CH3CH(OH)CN
Cl2 2Cl
CH3 CH2 CH2 CH2Cl
+ Cl + HCl + Cl2
Benzyl radical
68. 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
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62 Hydrocarbons Solutions of Assignment
ether HCl
69. Given reaction Br Mg X H2O Y(main product) Y in the reaction is
X Y(cyclohexane)
CH3 C CH2 — CH2 — Br CH3 C CH — CH3 CH3 C CH2 — CH3 CH2 C CH2 — CH3
H H Br Br Br H
(I) (II) (III) (IV)
NH2 Cl
(3) CH 3CH 2CH (4) CH3CH2CH
NH2 NH2
72. 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
73. An organic compound A(C 4 H 9 Cl) 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)
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Solutions of Assignment Hydrocarbons 63
74. In the following reaction
1. Mg, Ether
C6H5 CH2Br
X,
2. H3O
– +
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.
75. 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
–H
CH3 C C — CH3 CH3 C C — CH3
Addition of HBr to unsymmetrical alkene follow free radical mechanism and the addition is anti markovnikov's
addition.
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CH3
H2O/H
77. In the following reaction : H3C–C–CH = CH2 A + B
(Major (Minor
CH3 Product) Product)
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 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.
78. 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
(1) (2)
(3) (4)
S
Sol. Answer (1) 3
sp
Cyclopentane-1, 3-diene is a non aromatic compound since cyclic delocalization of 2 2
sp sp
electron is not possible because of the presence of sp3 hybridized carbon atom. sp
2 2
sp
80. Which one of the following compounds will be most easily attacked by an electrophile?
CH3
(1) (2)
Cl OH
(3) (4)
CH3
I. II.
OCH3 CF3
III. IV.
(1) IV < I < II < III (2) III < II < I < IV
(3) I < IV < III < II (4) II < III < I < IV
Sol. Answer (1)
Rate of electrophilic substitution depends on the electron density present over benzene ring. Among the
substituent present on benzene ring, their electron donating ability (+R effect) is in the order –OCH3>–CH3–
>–CF3. –CF3 is an electron withdrawing substituent. It will deactivate the benzene ring towards electrophilic
substitution. Therefore, correct order of electrophilic substitution
IV < I < II < III
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82. Among the following compounds (I-III) the correct order of rate of electrophillic substitution is
OCH3 NO2
I II III
SECTION - C
1. A : CHC–CH2–CH=CH2 adds up HBr to give CHC–CH2–CH–CH3 while CHC–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.
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.
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Solutions of Assignment Hydrocarbons 67
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.
–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)
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68 Hydrocarbons Solutions of Assignment
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.
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.
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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.
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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 CH C
O
CH C
O
maleic anhydride
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.
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.
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.
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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
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.
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