PREVIOUS HSE QUESTIONS AND ANSWERS OF THE CHAPTER “HYDROCARBONS”

1. Identify A and B in the following reaction :

OH

Zn/∆ A CH3Cl/ Anhyd. AlCl3 B (2)

Ans: A – Benzene (C6H6) and B – Toluene (C6H5-CH3)

2. An alkene on ozonolysis gives two molecules of ethanal. Identify the alkene. Draw its geometrical isomeric
forms. (2)
Ans: But-2-ene (CH3-CH=CH-CH3)
Its geometrical isomers are:

3. Briefly describe the following with suitable chemical equations :

(a) Wurtz reaction (b) Kharash effect (3) [July 2019]
Ans: (a) Wurtz reaction: Alkyl halides react with metallic sodium in dry ether to form alkanes. This
reaction is known as Wurtz reaction.

(b) Kharash Effect: In presence of organic peroxide, addition of HBr to unsymmetrical alkenes takes
place against Markovnikov rule. This is known as peroxide or Kharash effect.
e.g. CH3-CH= CH2 + HBr Org. peroxide CH3-CH2-CH2Br
Propene 1-bromopropane
4. Draw the Newman Projections of the eclipsed and staggered conformations of ethane molecule. (2)
Ans:

5. Give the chemical equations for the steps involved in the ozonolysis of propene. (2)
Ans: O
CH3-CH=CH2 + O3 CH3-CH CH2 CH3-CHO + HCHO
Propene O O Ethanal Methanal

6. Alkynes can be converted selectively into cis-alkenes and trans-alkenes. ExpIain with suitable examples. (3)
[March 2019]
Ans: Alkynes on partial reduction with dihydrogen in the presence of palladised charcoal partially
deactivated with sulphur compounds or quinoline give cis-alkenes.
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If we use sodium in liquid ammonia as the reducing agent, we get trans alkene.

7. Draw the 'sawhorse' projections of the eclipsed and staggered conformations of ethane. (2)
Ans:

8. Give the chemical equation for the conversion of hexane to benzene. Write the name of the process. (2)
Ans:

CH3-(CH2)4-CH3 Cr2O3 or V2O5 or Mo2O3

n-hexane 773K, 10-20 atm
Benzene
The process is known as Aromatisation.
9. Predict the Products :

(3) [August 2018]

Ans: a) 1-Bromopropane (CH3-CH2-CH2Br)
b) Benzene (C6H6)
c) Hexachlorobenzene (C6Cl6) Or,

10. What is Wurtz reaction? Give an example. (2)

Ans: Alkyl halides react with metallic sodium in dry ether to form alkanes. This reaction is known as
Wurtz reaction.

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11. Cycloheptatrienyl cation is given below :

Is this ion aromatic or not? Justify the answer. (2)

Ans: This compound is aromatic since it contains 6 delocalised π electrons according to Huckel’s rule.
12. Identify X, Y and Z in the following sequence of reactions :

(3) [March 2018]

O
Ans: X is CH3-CH=CH2, Y is CH3-CH CH2 and Z –isCH3-CHO
O O
13. a)

Cyclopentadienyl anion is aromatic. Why? (1)

b) Explain the following reactions: i) Substitution ii) Addition (2)
c) Ethyne is acidic in nature. Explain. (2) [July 2017]
Ans: a) This compound is aromatic since it contains 6 delocalised π electrons according to Huckel’s rule.
b) i) Substitution Reaction: It is the replacement of an atom or group of atom by another atom or atom
group. E.g.: Halogenation CH4 + Cl2 hυ CH3Cl + HCl
ii) Addition Reaction: It is the process of addition of simple molecules like H2, X2, HX etc. to an
unsaturated system.
CH2 = CH2 + HBr → CH3-CH2Br
c) In Ethyne, the H atoms are attached to sp hybridized carbon atoms. Due to the greater s-character
and electronegativity of sp hybridized C, it attracts the electron pairs of C – H bonds strongly. So the
hydrogen atom is readily removed as H+ and hence ethyne is acidic.
14. Benzene and benzeniod compounds show aromatic character.
a) Select the aromatic compounds from the following:

b) Suggest a method to convert ethyne to benzene. (2)

c) Give the products formed when benzene reacts with the following:
i) CH3Cl/AlCl3 ii) Cl2/hν [March 2017]
Ans: a)

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b) 3 C2H2 Red hot iron tube & 873K C6H6
c) i) Toluene
ii) Chlorobenzene
15. a) i) Complete the following reactions:

ii) Write the names of the above reactions? (2)

b) Baeyer’s reagent is used to find whether the compound is unsaturated or not. What is Baeyer’s reagent? (1)
c) What is the product formed when ethylene is treated with Baeyer’s reagent? (2) [September 2016]
Ans: a) i)
1) CH3-CH2-CH2-CH3
2) C6H5-CH3
ii) 1) Kolbe’s Electrolysis 2) Friedel Craft’s reaction
b) Cold dilute aqueous KMnO4
c) Ethylene glycol

16. a) 1-Alkynes are weakly acidic in nature. Give any two reactions to show the acidic character of ethyne. (2)
b) From the following, select the one in which Markownikoff’s rule is best applicable.
i) C2H4 + HCl ii) C3H6 + Br2 iii) C3H6 + HBr iv) C3H8 + Cl2 (1)
c) Hydrocarbons exhibit isomerism.
i) Name the type of isomerism exhibited by 2-Butene.
ii) Draw the structure of the isomers of 2-butene and select the one which is more polar. (2) [March 2016]
Ans: a) CH≡CH + Na → CH≡C-Na+ + ½ H2
CH3-C≡CH + Na → CH3-C≡C-Na+ + ½ H2
b) iii) C3H6 + HBr
c) i) Geometrical isomerism
ii)

Cis-But-2-ene is more polar than the trans form.

17. Controlled oxidation of alkanes in the presence of suitabie catalysts give a variety of products.
a) Complete the following reaction :
CH4 + O2 Mo2O3/heat ………………. + H2O (1)
b) Free rotation about a carbon-carbon single bond is permitted in an alkane molecule.

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What are conformers? Draw the structure of the eclipsed and staggered conformers of ethane in Sawhorse
and Newman projections and explain their relative stability. (4) [October 2015]
Ans: a) HCHO
b) The different spatial arrangements of atoms arising due to free rotation around a C-C single bond
are called conformations.
For projection formulas refer Question no. 4 and 7.
Staggered conformation is stabler than eclipsed form due to minimum repulsive forces between the
electron clouds of C-H bonds.
18. Write the IUPAC names of the following compounds:

Ans: a) Pent-4-en-2-ol
b) 2,5-Dimethylheptane
19. a) Complete the following chemical equations:

(1)

(1)

(1)
b) Explain the geometrical isomerism taking 2-Butene as an example. (2) [March 2015]
Ans: a)
i) CH3-CH2-CH2-CH3
ii) CH2=CH2
iii) C6H5-CH3 (Toluene)
b) Refer the answer of the question number 2.
20. a) Draw the cis and trans isomers of the following compound:
C2H5-C(CH3) = C(CH3)-C2H5. (2)
b) Complete the following reactions. (1)
i. 3CH ≡ CH Red hot iron tube at 873 K …………
ii. CaC2 + 2H2O Ca(OH)2 + ………….
c) Draw the sawhorse projections for eclipsed and staggered forms of an ethane molecule. (2)
Ans: a) 5H2C C2H5 5H2C CH3
C=C C=C
3HC CH3 3HC C2H5
Cis-isomer Trans-isomer
b) i) C6H6 (Benzene)
ii) C2H2 (Ethyne or acetylene)
c) Refer the answer of the question number 7.

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21. a) How is alkane prepared by Kolbe’s electrolytic method? (2)
b) Select the activating groups from the following: (1)
i) –NH2 ii) –SO3H iii) –CH3 iv) –COOH
c) What is ozonolysis? Write the names of the products obtained when propene undergoes ozonolysis? (2)
[August 2014]
Ans: a) In Kolbe’s electrolytic method, an aqueous solution of sodium or potassium salt of a carboxylic
acid is electrolysed to get an alkane.
2CH3COONa + 2H2O CH3 – CH3 + 2CO2 + 2NaOH + H2
Sod. Acetate ethane
b) –NH2 and –CH3
c) Alkenes add ozone to form an ozonide which on hydrolysis in presence of Zn to form aldehydes or
ketones. This reaction is known as ozonolysis.
O
CH3-CH=CH2 + O3 CH3-CH CH2 CH3-CHO + HCHO
Propene O O Ethanal Methanal
22. a) Write the products of the following chemical reactions and also name them.
i) 2CH3 – Br + 2Na dry ether …………………..
ii) CH3 – CH2Br alcoholic KOH …………………..
iii) CH3 – COONa NaOH/CaO ………………… (3)
b) An alkene ‘A’ on ozonolysis gave two molecules of formaldehyde. Write the name of ‘A’ and the chemical
equation of ozonolysis. (2) [March 2014]
Ans: a)
i) CH3-CH3 [Ethane]
ii) CH2=CH2 [Ethene or Ethylene]
iii) CH4 (Methane)
b) CH2=CH2 [Ethene or Ethylene]
O
CH2=CH2 + O3 CH2 CH2 2 H-CHO
Ethene O O Methanal

23. a) + 3Cl2 uv /500K A

Name the product A. (1)

b) Draw the Newman’s projections for the eclipsed and staggered conformations of n-butane. (2)
c) What is Baeyer’s reagent? Write the chemical equation of its reaction with ethylene (CH2=CH2). (2) [Sept. 2013]
Ans: a) Benzene hexachloride (BHC)

b) Refer the answer of the question number 4.

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c) Refer the answer of the question number 15 (b) and (c)
24. Free rotation is possible with respect to a C – C bond in the case of alkanes.
a) The repulsive interaction between the adjacent bonds in a conformation is called ………. (1)
b) Draw Newman’s projections of the two conformers of ethane. Which among these is more stable? Justify. (2)
c) An alkene on ozonolysis followed by reduction of the ozonide formed with zinc and water gave a mixture of
ethanal and methanal.
i) Identify the alkene. (1)
ii) Illustrate the above mentioned reaction using the chemical equation. (1) [March 2013]
Ans: a) Torsional strain
b) Refer the answer of the question number 4.
Staggered conformation is stabler than eclipsed form due to minimum repulsive forces between the
electron clouds of C-H bonds.
c) i) Propene
ii) Refer the answer of the question number 5.
25. a) Name the following reactions:
i) C6H14 Anhydrous AlCl3/HCl CH3 – CH – CH2 – CH2 – CH3
n-hexane CH3
2-Methyl pentane
ii) C6H14 V2O5/773K
10 – 20 atm
Benzene
iii) C6H14 773K C4H8 + C2H6
butene ethane (3 x 1 = 3)
b) Naphthalene is an aromatic compound. Explain its aromaticity using Huckel’s rule. (2) [September 2012]
Ans: a) i) Isomerisation
ii) Aromatisation
iii) Pyrolysis
b) According to Huckel’s rule, cyclic, planar, conjugated systems containing (4n+2) π electrons are
aromatic. Naphthalene contains 10 π electrons and follows this rule. So it is aromatic.
26. Hydrocarbons are organic compounds containing carbon and hydrogen only.
a) Complete the following chemical reactions:
i) 2CH3Br + 2 Na dry ether …………… + 2 NaBr
ii) …………… + Zn heat C6H6 + ZnO
iii) + 3Cl2 UV, 500K …………………. (3 x 1 = 3)

b) Analyze the following reaction:

CH3 – CH = CH2 + H – Br ‘A’ + ‘B’
If ‘A’ is the major product and ‘B’ is the minor product, identify ‘A’ and ‘B’. Also name the related rule. (2)
[March 2012]
Ans: a)
i) CH3 – CH3 (Ethane)
ii) C6H5-OH (Phenol)
iii) Benzene hexachloride or,

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b) A is CH3-CHBr-CH3 (2-Bromopropane) and B is CH3-CH2-CH2Br (1-Bromopropane). The rule behind the
selection of the major product is Markownikoff’s rule.
27. The higher homologue of benzene can be prepared by the following reaction.
CH3
+ A anhydrous AlCl3 + HCl

a) Identify the reagent A. (1)

b) Which named reaction is this? (1)
c) Write the reaction mechanism of this reaction. (3) [October 2011]
Ans:
a) CH3-Cl (Chloromethane)
b) Friedel Craft’s reaction
c) The mechanism involves the following steps:
i) Generation of Electrophile: CH3-Cl + AlCl3 CH3+ + [AlCl4]-
ii) Formation of carbocation:
H
+ CH3+ CH3
+
H
iii) Removal of a proton:
H
CH3
CH3 CH3
+ [AlCl4] – + HCl + AlCl3
H

28. a) Complete the following reactions:

i) CH3 – Br + Na dry ether ?
ii) CaC2 + H2O ?
iii) 3CH ≡ CH Red hot iron tube ? (3 x 1 = 3)
873 K
b) Illustrate Markovnikov’s rule taking the example of propene. (2) [March 2011]
Ans: a)
i) CH3-CH3 (Ethane)
ii) C2H2 (Ethyne or Acetylene)
iii) C6H6 (Benzene)
b) Markownikoff’s (Markovnikov’s) rule states that when an unsymmetrical reagent is added to an
unsymmetrical alkene, the negative part of the addendum (adding molecule) gets attached to the
carbon containing lesser number of hydrogen atoms.
E.g. When HBr is added to propene, we get 2 products – 1-bromopropane and 2-bromopropane.

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Here 2-bromopropane is the major product.
29. In a special condition, addition of HBr to unsymmetrical alkene takes place contrary to Markovnikov’s rule.
a) What is the special condition? (1)
b) Give the mechanism of anti Markovnikov’s addition of HBr to propene. (4) [September 2010]
Ans: a) The special condition is the presence of organic peroxide.
b) Mechanism of anti Markovnikov’s addition

30. a) The spacial arrangements of atoms which can be converted into one another by rotation around a C – C
single bond are called conformations.
i) Represent Sawhorse and Newman projection formulae of staggered and eclipsed conformations of
ethane. (2)
ii) Compare the stabilities of staggered and eclipsed conformations. (1)
b) Consider the reaction given below:

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CH3 – CH = CH2 + HBr CH3 – CHBr – CH3 + CH3 – CH2 – CH2Br
i) Identify the major product obtained. (1)
ii) Name the rule governing the formation of the major product. (1) [March 2010]
Ans: a)
i) Refer the answer of the question number 4 and 7.
ii) Staggered conformation is stabler than eclipsed form due to minimum repulsive forces between
the electron clouds of C-H bonds.
b) i) CH3 – CHBr – CH3 (2-Bromopropane)
ii) Markovnikov’s rule.
31. a) How will you prepare ethane by Kolbe’s electrolytic method? (2)
b) Expalin the Markovnikov’s rule for the addition reaction using a suitable example. (3) [March 2009]

Ans: a) By the electrolysis of aqueous solution of sodium or potassium acetate.

2CH3COONa + 2H2O CH3 – CH3 + 2CO2 + 2NaOH + H2
Sod. Acetate Ethane
b) Refer the answer of the question number 28 (b)
32. a) Consider the reaction between benzene and nitrating mixture.

+ HNO3 Conc. H2SO4 ? (1)

b) What is the reacting species in the above reaction? (1)

c) How is the species formed in the system? (1) [[June 2008]
Ans: a)

b) Nitronium ion (NO2+)

c) It is produced by the transfer of a proton from H2SO4 to HNO3 followed by dehydration of the
resulting product.

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