CBSE Class 11 Chemistry

NCERT Exemplar Solutions

Chapter – 13
Hydrocarbons

Multiple Choice Questions (Type-I)

1. Arrange the following in decreasing order of their boiling points.

(A) n-butane (B) 2–methyl butane
(C) n-pentane (D) 2, 2–dimethylpropane
(i) A > B > C > D
(ii) B > C > D > A
(iii) D > C > B > A
(iv) C > B > D > A
Ans: (iv) C > B > D > A
The boiling point increases with the increase in the length of the side chain. However,
with the branching, the boiling point decreases due to the decrease in the surface area.

2. Arrange the halogens F2, Cl2, Br2, I2, in order of their increasing reactivity with
alkanes.
(i) I2 < Br2 < Cl2 < F2
(ii) Br2 < Cl2 < F2 < I2
(iii) F2 < Cl2 < Br2 < I2
(iv) Br2 < I2 < Cl2 < F2
Ans: (i) I2 < Br2 < Cl2 < F2

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The reactivity of halogens with alkanes depends on the electronegativity i.e. higher the
electronegativity higher would be the reaction. As down the group reactivity decrease
so thus its reactivity.

3. The increasing order of reduction of alkyl halides with zinc and dilute HCl is
(i) R–Cl < R–I < R–Br
(ii) R–Cl < R–Br < R–I
(iii) R–I < R–Br < R–Cl
(iv) R–Br < R–I < R–Cl
Ans: (ii) R–Cl < R–Br < R–I
The reduction of alkyl halides depends upon the C-X bond strength i.e. lesser the bond
strength higher will be the reactivity of alkyl halide. As down the group size of the
halogens increases thus the bond strength decreases.

4. The correct IUPAC name of the following alkane is

(i) 3, 6 – Diethyl – 2 – methyl octane

(ii) 5 – Isopropyl – 3 – ethyl octane
(iii) 3 – Ethyl – 5 – isopropyl octane
(iv) 3 – Isopropyl – 6 – ethyl octane
Ans: (i) 3, 6 – Diethyl – 2 – methyl octane
Octane is the longest chain here and the side chain follows the lowest sum rule.

5. The addition of HBr to 1-butene gives a mixture of products A, B and C

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The mixture consists of
(i) A and B as major and C as minor products
(ii) B as major, A and C as minor products
(iii) B as minor, A and C as major products
(iv) A and B as minor and C as major products
Ans: (i)
The reaction follows Markovnikov’s rule leading to giving 2o carbocation as an
intermediate.

6. Which of the following will not show geometrical isomerism?

Ans: (iv)
The two substituents attached to the same C atom of the C=C bond should be different
to exhibit geometrical isomerisms.

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7. Arrange the following hydrogen halides in order of their decreasing reactivity
with propene.
(i) HCl > HBr > HI
(ii) HBr > HI > HCl
(iii) HI > HBr > HCl
(iv) HCl > HI > HBr
Ans: (iii)
The addition of alkyl halides to propene depends upon the H-X bond strength i.e.
lesser the bond strength higher will be the reactivity of the alkyl halide. As down the
group size of the halogens increases thus the bond strength decreases.

8. Arrange the following carbanions in order of their decreasing stability.

(A) H 3C - C ≡ C-

(B) H - C ≡ C-
−
(C) H 3C - CH 2

(i) A > B > C

(ii) B > A > C
(iii) C > B > A
(iv) C > A > B
Ans: (ii)
The electronegativity of sp hybridization is higher than that of sp3 hybridization.
The +I effect destabilizes the carbanion.

9. Arrange the following alkyl halides in decreasing order of the rate of β–

elimination reaction with alcoholic KOH.

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(i) A > B > C
(ii) C > B > A
(iii) B > C > A
(iv) A > C > B
Ans: (iv)
The order of reactivity of β– elimination reaction is 3o>2o>1o

10. Which of the following reactions of methane is incomplete combustion:

(i) 2CH4 + O2 

Cu/523K/100atm
→ 2CH3OH

(ii) CH4 + O2 

M 2 O3
→ HCHO + H2O
(iii) CH4 + O2 → C (s) + 2H2O (l)
(iv) CH4 + O2 → CO2 (g) + 2H2O (l)
Ans: (iii)
As the unburn carbon left out in this reaction thus it is an incomplete reaction

Multiple Choice Questions (Type-II)

11. Some oxidation reactions of methane are given below. Which of them is/are
controlled oxidation reactions?
(i) CH4 + O2 → CO2 (g) + 2H2O (l)
(ii) CH4 + O2 → C (s) + 2H2O (l)

(iii) CH4 + O2 

M 2 O3
→ HCHO + H2O

(iv) 2CH4 + O2 

Cu/523K/100atm
→ 2CH3OH

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Ans: (iii) & (iv)
Methane is a controlled oxidation reaction that leads to giving formaldehyde and
methanol.

12. Which of the following alkenes on ozonolysis give a mixture of ketones only?

Ans: (iii) & (iv)

When only the alkyl group is attached to the C atom of the C=C bond then only it
would lead to giving only ketone on ozonolysis.

13. Which are the correct IUPAC names of the following compound?

(i) 5– Butyl – 4– isopropyldecane

(ii) 5– Ethyl – 4– propyldecane
(iii) 5– sec-Butyl – 4– iso-propyldecane
(iv) 4–(1-methylethyl)– 5 – (1-methylpropyl)-decane
Ans: (iii) & (iv)

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The longest carbon chain is of 10 carbon atom

14. Which are the correct IUPAC names of the following compound?

Ans: (i) & (iv)

The longest carbon chain is of 10 carbon atom

15. For an electrophilic substitution reaction, the presence of a halogen atom in

the benzene ring _______.
(i) deactivates the ring by inductive effect
(ii) deactivates the ring by resonance
(iii) increases the charge density at ortho and para position relative to meta
position by resonance
(iv) directs the incoming electrophile to meta position by increasing the charge
density relative to ortho and para position.
Ans: (i) & (iii)
The halogens atom weakly deactivate the ring due to the -I effect and directs the
incoming group to the ortho and para position due to the +R effect.

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16. In an electrophilic substitution reaction of nitrobenzene, the presence of nitro
group ________.
(i) deactivates the ring by inductive effect.
(ii) activates the ring by inductive effect.
(iii) decreases the charge density at ortho and para position of the ring relative to
meta position by resonance.
(iv) increases the charge density at meta position relative to the ortho and para
positions of the ring by resonance
Ans: (i) & (iii)
The nitro group strongly deactivate the ring due to the -R effect and -I effect

17. Which of the following are correct?

(i) CH3—O—CH2⊕ is more stable than CH3—CH2⊕
(ii) (CH3)2CH⊕ is less stable than CH3—CH2—CH2⊕
(iii) CH2=CH—CH2⊕ is more stable than CH3—CH2—CH2⊕
(iv) CH2=CH⊕is more stable than CH3—CH2⊕
Ans: (i) & (iii)
The +I effect of the -OCH3 group stabilizes the carbocation.
The two resonating structure of CH2=CH-CH2⊕ ↔ ⊕CH -CH=CH
2 2 makes it more
stable

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18. Four structures are given in options (i) to (iv). Examine them and select the
aromatic structures.

Ans: (i) & (iii)

The structures that follow the (4n+2) Huckle rule of aromaticity is considered to be
aromatic

19. The molecules having dipole moment are __________.

(i) 2, 2-Dimethylpropane
(ii) trans-Pent-2-ene
(iii) cis-Hex-3-ene
(iv) 2, 2, 3, 3 - Tetramethylbutane.
Ans: (ii) & (iii)

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Short Answer Type

20. Why do alkenes prefer to undergo electrophilic addition reactions while

arenes prefer electrophilic substitution reactions? Explain.
Ans: If arenes would undergo electrophilic addition reaction then they would lose
their aromaticity which would lead to comparatively less stability. However, alkenes
undergo electrophilic addition reaction via carbocation intermediate.

21. Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will
the butene thus formed on reduction of 2-butyne show the geometrical
isomerism?
Ans: Yes, it will execute geometrical isomerism as the product formed can be either
cis-2-butene or trans-2-butene.

22. Rotation around carbon-carbon single bond of ethane is not completely free.
Justify the statement.
Ans: The rotation around C-C single bond is possible but it is not completely free due
to the torsional strain which is about 1-20 KJ mol-1.

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23. Draw Newman and Sawhorse projections for the eclipsed and staggered
conformations of ethane. Which of these conformations is more stable and why?
Ans:

The staggered conformation is more stable because of comparatively less torsional

strain.

24. The intermediate carbocation formed in the reactions of HI, HBr and HCl
with propene is the same and the bond energy of HCl, HBr and HI is 430.5 kJ
mol–1, 363.7 kJ mol–1 and 296.8 kJ mol–1 respectively. What will be the order of
reactivity of these halogen acids?
Ans: The rate-determining step involved in the reaction is
CH3-CH=CH2 + HX → CH3-CH+-CH3 + X-
So the rate-determining step depends on the bond energy of HX i.e. higher the bond
energy lesser would be reactivity.

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Thus the order of reactivity of these halogen acids is
HI > HBr > HCl

25. What will be the product obtained as a result of the following reaction and
why?

Ans: The benzene here would undergo Friedel-Crafts alkylation reaction where
carbocation is formed as an intermediate, thus secondary carbocation is formed as an
intermediate due to its greater stability than that of the primary carbocation.
The final product obtained is

26. How will you convert benzene into

(i) p – nitrobromobenzene
(ii) m – nitrobromobenzene
Ans:
(i)

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(ii)

27. Arrange the following set of compounds in the order of their decreasing
relative reactivity with an electrophile. Give reason

Ans: The electron donating group increases the reactivity in electrophilic substitution
reaction whereas the electron withdrawing group decreases the reactivity in
electrophilic substitution.
Thus, the order of reactivity

28. Despite their - I effect, halogens are o- and p-directing in haloarenes. Explain.
Ans: Due to the +R effect halogens are ortho and para directing groups.

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29. Why does presence of a nitro group make the benzene ring less reactive in
comparison to the unsubstituted benzene ring. Explain.
Ans: The nitro group strongly deactivate the benzene towards the electrophilic
substitution reaction due to the -R and -I effect

30. Suggest a route for the preparation of nitrobenzene starting from acetylene?
Ans:

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31. Predict the major product (s) of the following reactions and explain their
formation.
(Ph −CO −O)2
H 3C − CH
= CH 2  HBr
→
HBr
H 3C =
− CH CH 2   →

Ans: In presence of (Ph-CO-O)2 it lead to CH3-CH2-CH2Br as the reaction undergo by

free radical mechanism
However in absence of (Ph-CO-O)2 the reaction undergo by carbocation intermediate
thus lead to give CH3-CHBr-CH3

32. Nucleophiles and electrophiles are reaction intermediates having electron

rich and electron deficient centres respectively. Hence, they tend to attack
electron deficient and electron rich centres respectively. Classify the following
species as electrophiles and nucleophiles.
(i) H3CO-
O
(ii) ||
H 3C - C - O -
•
(iii) Cl
(iv) Cl 2C :

(v) (H3C)3C+
(vi) Br-
(vii) H3COH
(viii) R-NH-R
Ans:

Electrophiles Nucleophiles
(iii), (iv), (v) (i), (ii), (vi), (vii), (viii)

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33. The relative reactivity of 1°, 2°, 3° hydrogen’s towards chlorination is 1 : 3.8 :
5. Calculate the percentages of all monochlorinated products obtained from 2-
methylbutane.
Ans: The structure of 2-methylbutane is

Total number Total amount of monochlorinated % of monochlorinated

Product product
10 9 9 41.7
20 2 7.6 35.2
30 1 5 23.1

34. Write the structures and names of products obtained in the reactions of
sodium with a mixture of 1-iodo-2-methylpropane and 2-iodopropane.
Ans: It is a Wurtz reaction where alkane is formed.

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35. Write hydrocarbon radicals that can be formed as intermediates during
monochlorination of 2-methylpropane? Which of them is more stable? Give
reasons
Ans: The 2-methylpropane would lead to two types of radicals.

Among the two 3o radical is most stable as it contains 9 α -hydrogen whereas 1o

radical contains only 1 α -hydrogen.

36. An alkane C8H18 is obtained as the only product on subjecting a primary alkyl
halide to Wurtz reaction. On monobromination this alkane yields a single isomer
of a tertiary bromide. Write the structure of alkane and the tertiary bromide.
Ans: The reaction is

The alkane is

The tertiary bromide is

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37. The ring systems having following characteristics are aromatic.
(i) Planar ring containing conjugated π bonds.
(ii) Complete delocalisation of the π−electrons in ring system i.e. each atom in the
ring has unhybridised p-orbital, and
(iii) Presence of (4n+2) π−electrons in the ring where n is an integer (n = 0, 1,
2,...........) [Huckel rule].
Using this information classify the following compounds as aromatic /
nonaromatic.

Ans:

Aromatic Non-aromatic
A, C, E, F B, D, G

38. Which of the following compounds are aromatic according to Huckel’s rule?

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Ans: As per the Huckel (4n+2) rule following distinction can be made:-

Aromatic Non aromatic

B, D, F A, C, E

39. Suggest a route to prepare ethyl hydrogensulphate (CH3–CH2–OSO2—OH)

starting from ethanol (C2H5OH).
Ans:

Matching Type

40. Match the reagent from Column I which on reaction with

CH3 – CH = CH2 gives some product given in Column II as per the codes given
below:

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 Column I Column II
(i) O3/Zn + H2O (a) Acetic acid and CO2
(ii) KMnO4/H+ (b) Propan-1-ol
(iii) KMnO4/OH- (c) Propan-2-ol
(iv) H2O/H+ (d) Acetaldehyde and formaldehyde
(v) B2H6/NaOH and H2O2 (e) Propan-1,2-diol
Ans:

(i) O3/Zn + H2O (d) Acetaldehyde and formaldehyde

(ii) KMnO4/H+ (a)Acetic acid and CO2
(iii) KMnO4/OH- (e) Propan-1,2-diol
(iv) H2O/H+ (c) Propan-2-ol
(v) B2H6/NaOH and H2O2 (b) Propan-1-ol

41. Match the hydrocarbons in Column I with the boiling points given in Column
II.

Column I Column II
(i) n-pentane (a) 282.5 K
(ii) iso-pentane (b) 309 K
(iii) neo-pentane (c) 301 K
Ans:

(i) n-pentane (b) 309 K

(ii) iso-pentane (c) 301 K
(iii) neo-pentane (a) 282.5 K

42. Match the following reactants in Column I with the corresponding reaction
products in Column II.

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 Column I Column II
AlCl3
(i) Benzene + Cl2  → (a) Benzoic acid
AlCl3
(ii) Benzene + CH3Cl  → (b) Methyl phenyl ketone
AlCl3
(iii) Benzene + CH3COCl  → (c) Toluene
KMnO 4 / NaOH
(iv) Toluene  → (d) Chlorobenzene

(e) Benzene hexachloride

Ans:

AlCl3
(i) Benzene + Cl2  → (d) Chlorobenzene
AlCl3
(ii) Benzene + CH3Cl  → (c) Toluene
AlCl3
(iii) Benzene + CH3COCl  → (b) Methyl phenyl ketone
KMnO 4 / NaOH
(iv)Toluene  → (a) Benzoic acid

43. Match the reactions given in Column I with the reaction types in Column II.

Column I Column II
H
(i) CH2=CH2 + H2O 
+
→ CH3CH2OH (a) Hydrogenation

(ii) CH2=CH2 + H2 
Pd
→ CH3CH3 (b) Halogenation

(iii) CH2=CH2 + Cl2 → ClCH2CH2Cl (c) Polymerisation

(iv) 3CH ≡ CH  Cu


tube heat
→ C6H6 (d) Hydration

(e) Condensation
Ans:

H
(i) CH2=CH2 + H2O 
+
→ CH3CH2OH (d) Hydration
Pd
(ii) CH2=CH2 + H2  → CH3CH3 (a) Hydrogenation

(iii) CH2=CH2 + Cl2 → ClCH2CH2Cl (b) Halogenation

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 (iv) 3CH ≡ CH  Cu

tube heat
→ C6H6 (c) Polymerisation

Assertion and Reason Type

In the following questions a statement of assertion (A) followed by a statement of

reason (R) is given. Choose the correct option out of the choices given below each
question.

44. Assertion (A): The compound cyclooctane has the following structural
formula:

It is cyclic and has conjugated 8π-electron system but it is not an aromatic

compound.
Reason (R): (4n + 2) π electrons rule does not hold good and ring is not planar.
(i) Both A and R are correct and R is the correct explanation of A.
(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.
Ans: (i)
Because cyclooctatetraene is tubbed shaped.

45. Assertion (A): Toluene on Friedal Crafts methylation gives o– and p–xylene.
Reason (R): CH3 - group bonded to benzene ring increases electron density at o–
and p– position.
(i) Both A and R are correct and R is the correct explanation of A.

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(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.
Ans:
(i) The -CH3 group is an activating group and it directs the upcoming substituent to the
ortho and para position.

46. Assertion (A): Nitration of benzene with nitric acid requires the use of
concentrated sulphuric acid.
Reason (R): The mixture of concentrated sulphuric acid and concentrated nitric
acid produces the electrophile, NO2 +.
(i) Both A and R are correct and R is the correct explanation of A.
(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.
Ans: (i)
The sulphuric acid helps in furnishing NO2+ (electrophile).

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47. Assertion (A): Among isomeric pentanes, 2, 2-dimethylpentane has highest
boiling point.
Reason (R): Branching does not affect the boiling point.
(i) Both A and R are correct and R is the correct explanation of A.
(ii) Both A and R are correct but R is not the correct explanation of A.
(iii) Both A and R are not correct.
(iv) A is not correct but R is correct.
Ans: (iii)
With the branching the boiling decreases due to the decrease in surface area which
leads to decrease its van der Waals force.

Long Answer Type

48. An alkyl halide C5H11Br (A) reacts with ethanolic KOH to give an alkene ‘B’,
which reacts with Br2 to give a compound ‘C’, which on dehydrobromination
gives an alkyne ‘D’. On treatment with sodium metal in liquid ammonia one mole
of ‘D’ gives one mole of the sodium salt of ‘D’ and half a mole of hydrogen gas.
Complete hydrogenation of ‘D’ yields a straight chain alkane. Identify A,B, C
and D. Give the reactions invovled.

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Ans:

49. 896 mL vapour of a hydrocarbon ‘A’ having carbon 87.80% and hydrogen
12.19% weighs 3.28g at STP. Hydrogenation of ‘A’ gives 2-methylpentane. Also
‘A’ on hydration in the presence of H2SO4 and HgSO4 gives a ketone ‘B’ having
molecular formula C6H12O. The ketone ‘B’ gives a positive iodoform test. Find
the structure of ‘A’ and give the reactions involved.
3.28  22400
×
Ans: The molar mass of the compound = = 831gmol-1
896

Element Percentage At.mass Relative ratio Simplest ratio

C 87.8% 12 7.31 3
H 12.19% 1 12.19 5

Thus the empirical formula of the compound is C3H5

Molecular formula =n x empirical formula = (831/41) x C3H5 = C6H10

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50. An unsaturated hydrocarbon ‘A’ adds two molecules of H2 and on reductive
ozonolysis gives butane-1,4-dial, ethanal and propanone. Give the structure of
‘A’, write its IUPAC name and explain the reactions involved.
Ans: The structure of A is
The reaction involved are as follows:

51. In the presence of peroxide addition of HBr to propene takes place according
to anti Markovnikov’s rule but peroxide effect is not seen in the case of HCl and
HI. Explain.

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Ans: The bond energy of HCl is higher than that of HBr thus it is not cleaved by free
radical mechanism to exhibit peroxide effect. However in case of HI the bond energy
is so low that the iodine radical forms readily and after formation it combines to form
an iodine molecule.

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