DELHI PUBLIC SCHOOL BANGALORE NORTH(2021-22)

HYDROCARBONS
WORKSHEET-ANSWER KEY

CLASS-XI SUBJECT: CHEMISTRY

1. Do the following conversions and name the reactions:

(i) Bromoethane to n-Butane
(ii) Chloroethane to Ethene.
(iii) Benzene to Toluene.
ANS:
(i) WURTZ REACTION:

(ii) DEHYDROHALOGENATION:

(iii) FRIEDEL- CRAFT’S ALKYLATION:

2. Complete the following equations:

Hg2+/H+
(i) HC≡CH + H2O ----------→
NaNH2
(ii) BrCH2-CH2Br + KOH ----------→ X -------→ Y.

CaO, heat
(iii) C6H5COONa + NaOH-----------→
ANS:
Hg2+/H+
(i) HC≡CH + H2O ----------→ CH2=CH-OH <----> CH3CHO

∆ NaNH2
(ii) BrCH2-CH2Br + KOH ----------→ BrCH=CH2 --------------→ CH≡CH .
-KBr, H2O -NaBr, - NH3

CaO, heat
 (iii) C6H5COONa + NaOH-----------→ C6H6 + Na2CO3

3. Phenol on nitration forms o-nitrophenol and p- nitrophenol but benzoic acid on nitration forms a
meta product, m-nitrobenzoic acid. Why?
ANS:
−OH group in phenol shows +M effect (positive resonance effect) and increases the electron
density at ortho and para positions, thus forcing the NO2+ to be attached on o, p− positions
whereas in benzoic acid, -COOH group withdraws electron density from the benzene ring. So the
incoming NO2+ goes to meta position.

4. Which of the following compounds is aromatic and why?

(i) (ii)
ANS:
The compound (ii) is aromatic as it obeys Huckel’s rule.
(Hint: For a compound to be considered aromatic, it must be flat, cyclic, and conjugated
and it must obey Huckel's rule. Huckel's rule states that an aromatic compound must
have 4n+2 pi electrons in the overlapping p orbitals in order to be aromatic (n in this
formula represents any integer).

5. How will you prepare 2-bromopropane from propene. Give the mechanism involved in the
reaction and also name the rule followed.
ANS:

MECHANISM:
This reaction follows Markovnikov’s rule where the negative part of the addendum is
attached to the carbon atom having a lesser number of hydrogen atoms.
Step – 1:Hydrogen bromide provides an electrophile, H+. This electrophile attacks the
double bond to form 1° and 2° carbocations as shown below:-

Step – 2: Secondary carbocations are more stable than primary carbocations. Hence, the
former predominates since it will form at a faster rate. Thus, in the next step, Br– attacks
 the carbocation to form 2 – bromopropane as the major product.

6. Give reasons for the following:

(i) Benzene undergoes substitution reactions rather than addition though it contains three
double bonds.
(ii) Wurtz reaction is not preferred to prepare alkanes containing odd number of carbon atoms.
(iii) Methane cannot be prepared by Kolbe’s electrolysis.
ANS:
(i) Benzene is resonance stabilized due to the delocalisation of pi electrons. Benzene
resists addition reactions because that would involve breaking the delocalisation and
losing that stability.
(ii) Wurtz reaction is not preferred for the preparation of alkanes containing odd number of
carbon atoms since many side products are formed and a mixture of alkanes is formed because
both alkyl halides react with each other and also with themselves.
(iii) Kolbe's electrolysis method is suitable for the prepartion of symmetrical alkanes,
that is alkanes containing even number of carbon atoms.Methane has only one carbon,
hence if cannot be prepared by this method.

7. What are geometrical isomers? Draw the geometrical isomers of 2, 3-Dichlorobut-2-ene. Which
of the two geometrical isomers has high melting point and why?
ANS:
Geometrical isomers are the compounds which contain the same number and types of
atoms,and bonds but which have different spatial arrangements of the atoms.

Trans isomer has higher melting point due to its symmetrical structure which
results in better packing.

8. Draw the Sawhorse and Newman conformations of ethane. Explain the stability of staggered
form. Is it possible to separate the conformers of a molecule?
ANS:
 The eclipsed conformation is said to suffer torsional strain because of repulsive forces
between electron pairs in the C―H bonds of adjacent carbons. These repulsive forces
are minimized in the staggered conformation since all C―H bonds are as far from one
another as possible.
It is not possible to isolate pure staggered form of ethane or pure eclipsed form of
ethane at room temperature because of less difference in their energy they can get
converted into each other very fast.

9. Give the balanced chemical equation for the following:

a) Phenol is heated with zinc dust.
b) Electrolysis of Sodiumethanoate
c) Water is added to ethyne in the presence of H2SO4 and HgSO4.
ANS:

a)

b)

c)
Tautomerisation

10. Chlorine is an electron-withdrawing group, yet it is ortho-, para- directing in electrophilic

aromatic substitution reactions. Why?
 ANS:
Chlorine withdraws electrons through inductive effect(-I effect) and releases electrons
through resonance(+R). Due to resonance, electron density is increased
on ortho and para position hence chlorine is an o, p directing group.

11. Arrange the following in each set, in the increasing order of the property mentioned and state
the reason for your answer:
a. Ethane, Propane, 2- Methylpropane, 2,2-Dimethylpropane(boiling point)
b. CH3-CH3, CH2=CH2, CH ≡ CH( acidic character)
ANS:
a. Ethane > Propane > 2- Methylpropane > 2,2-Dimethylpropane ( As the branching
increases, surface area decreases and hence the intermolecular force of attraction
decreases.
b. CH3-CH3 < CH2=CH2 < CH ≡ CH( The carbon atoms in ethyne are sp hybridized. They
have more s-character than sp2 and sp3 carbons, hence ethyne is the most acidic.

12. Iodination of alkanes is carried out in the presence of an oxidising agent such as nitric acid.
Give reason.
ANS: Iodination of alkanes is a reversible reaction, so it is carried out in the presence of
oxidising agents like HIO3 or HNO3. The oxidising agent oxidizes HI into I2.

13. Covert 1-Bromopropane into 2- Bromopropane.

ANS:

Word problems:
1. An organic compound ‘A’ on heating with concentrated sulphuric acid forms a hydrocarbon ‘B’.
When ‘B’ reacts with ozone it forms an aldehyde ‘C’ containing one carbon. Identify the
compounds A, B, and C and give the reactions involved.
2. An alkene X adds one molecule of Ozone to form a mixture of methanal and ethanal. Identify
the compound X and give the reaction involved.
3. Benzene on heating with nitrating mixture forms a compound A which on chlorination gives B.
Identify the compounds A and B and give the reactions involved.
4. A compound X on dehydration forms the compound Y. Y decolourises bromine in carbon
tetrachloride by taking one molecule of bromine to form 1,2-dibromoethane. Identify X, and Y
and give the reactions involved.
ANSWERS:
1. A= CH3CH2OH, B= CH2=CH2, C= HCHO
 conc. H2SO4, 443K O3
CH3CH2OH---------------------------> CH2=CH2 ------------> 2HCHO

2. X= CH3CH=CH2

3. A= Nitrobenzene, B= m-Chloronitrobenzene.

4. X= CH3CH2OH, Y= CH2=CH2
conc. H2SO4, heat Br2 in CCl4
CH3CH2OH--------------------------> CH2=CH2--------------------> BrCH2CH2Br

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