HANSRAJ SMARAK SENIOR SECONDARY SCHOOL

POCKET - E DILSHAD GARDEN

ASSIGNMENT - HYDROCARBONS
Class 11 - Chemistry

Section A
1. What do you understated by Resonance energy?
2. State Markownikov’s Rule.
3. Write the IUPAC names of the following compounds.

i.

ii.

iii. CH2 = C (CH2CH2CH3)2

iv.

4. Why the addition of inert gas does not change the equilibrium?
5. Write structural formulae of the following compounds.
i. 3, 4, 4, 5-tetramethylheptane
ii. 2, 5-dimethylhexane
6. How will you convert benzene into
i. p - nitrobromobenzene
ii. m - nitrobromobenzene
7. What happens when benzene is treated with an excess of

in the presence of sunlight? Give chemical reaction.

8. Write IUPAC name: CH2 = CH − c ≡ C − CH3

9. The boiling point of hydrocarbons decreases with an increase in branching. Give reason.
10. How is benzene converted to benzene hexachloride?
11. Propanal and pentane-3-one are the ozonolysis products of an alkene. What is the structural formula
of the alkene?
12. An alkene (molecular weight = 56) on reaction with trioxygen followed by zinc/CH3COOH gave only

ethanal. Identify the Structure of the alkene.

13. Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will the butene thus
formed on the reduction of the 2-butyne show the geometrical isomerism?

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14. Sodium salt of which acid will be needed for the preparation of propane? Write chemical equation for
the reaction.
15. Suggest a route to prepare ethyl hydrogensulphate (CH3 - H2 - OSO2 - OH) starting from ethanol

(C2H5OH).
16. Convert ethylene to ethane.
17. Which is more acidic: ethene or ethyne and why?
18. How is phenol reduced to benzene?
19. Cyclobutane is less reactive than cyclopropane. Justify.
20. Rotation around carbon-carbon single bond of ethane is not completely free. Justify the Statement.
21. What is β-elimination reaction?
22. On converting benzene to toluene, state whether there will be a rise or fall in the melting point.
23. 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.
24. The boiling point of alkanes shows a steady increase with an increase in molecular mass. Why?
25. Write equations for the preparation of
i. HC≡ CD and
ii. DC≡ CD
Section B
26. Write the IUPAC names of the following compounds.

i.

ii.

iii.

Also calculate the number of σ  and π -bonds.

27. N-pentane has a higher boiling point than neopentane but the melting point of neopentane is higher
than that of n-pentane.
28. (a) Why are alkenes called unsaturated hydrocarbons?
(b) How will you test the presence of double bond in an alkene?
(c) Name the products formed when propene is subjected to ozonolysis.
29. Define substitution reactions. Why do benzene undergo substitution reactions even though they
contain double bonds?
30. Explain Wurtz reaction with an example.
31. What are the necessary conditions for any system to be aromatic?
32. Discuss the preparation of alkanes by Wurtz reaction. What is the limitation of the reaction?
33. Why does benzene undergo electrophilic substitution reactions easily and nurcleophilic substitutions
with difficulty?
34. Arrange benzene, n-hexane, and ethyne in decreasing order of acidic behaviour. Also, explain the
reason for this behaviour.

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35. An alkene ‘A' contains three C—C σ -bonds, eight C—H σ -bonds and one C—C π -bond. ‘A' on ozonolysis
gives two moles of an aldehyde of molar mass 44 u. Write IUPAC name of 'A'.
36. Out of benzene, m-dinitrobenzene and toluene which will undergo nitration most easily and why?
37. Discuss the hybridization of carbon atoms in alkene C2H4 and show the π-orbital overlaps.
38. 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.
39. 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 involved.
40. Write structures of different chain isomers of alkanes corresponding to the molecular formula C6H14.
Also, write their IUPAC names.
41. Write structures of different isomeric alkyl groups corresponding to the molecular formula C5H11.

Write IUPAC names of alcohols obtained by attachment of –OH groups at different carbons of the
chain.
42. Write chemical equations for the combustion reaction of the following hydrocarbons.
a. Butane
b. Pentene
c. Hexyne
d. Toluen
43. Write IUPAC names of the following compounds
i. (CH3)3CCH2C(CH3)3
ii. (CH3)2C(C2H5)2

iii. Tetra-tert-butylmethane
44. Explain the term polymerization with two examples.
45. 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.
46. Draw Newman and Sawhorse projections for the eclipsed and staggered conformations of ethane.
Which of these conformations is more stable and why?
47. An alkene 'A' on ozonolysis gives a mixture of ethanal and pentan-3-one. Write the structure and
IUPAC name of 'A'.
48. The dipole moment of trans 1,2-dichloroethane is less than the cis – isomer. Explain.

49. In the alkane H3C–CH2– C(CH3)2–CH2–CH(CH3)2, identify 1o, 2o, 3o carbon atoms and give the number
of H atoms bonded to each one of these.
50. Write structures of all the alkenes which on hydrogenation give 2-metlrylbutane.
Section C
51. i. The reductive ozonolysis of an alkene gave butanone and propanal. Write the structure of alkene
and its IUPAC name.

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 ii. Ozonolysis of an alkene X followed by decomposition with water and a reducing agent gave a
mixture of two isomers of the formula C3H6O. Given the structure of the alkene and its IUPAC

name.
52. i. Draw the two geometrical isomers of but 2-en-1, 4-dioic acid. Which of these will have a higher
dipole moment?
ii. How many isomers are possible for monosubstituted and disubstituted benzene?
53. i. Write structures of all the alkenes which on hydrogenation give 2-methylbutane.
ii. Out of benzene, m-dinitrobenzene and toluene which will undergo nitration most easily and why?
54. Explain the term aromaticity. What are the necessary condition for any compound to show
aromaticity?
55. i. How would you separate propene from propyne?
ii. How would you carry out the following conversations?
a. H3CCH2CH=CH2 → H3C-CH2CH2CH2OH

b. H3C CH2-CH=CH2 → H3C-CH2-CH(OH)CH2OH

c. H3CC=CH → H3C COCH3

d. Br2CHCHBr2 → HC=CH

56. SN1 reaction is a first-order nucleophilic substitution, e.g.,

C H3 C H3

| |

C H3 − C − Br + h2 o →C H3 − C − OH + HBr
| |

C H3 C H3

The concentration of nucleophilic does not appear in the rate law expression:
Reaction rate = k[RX]
In a multistep organic reaction, the rate-limiting step is the slowest step. The rate-determining step is
represented by the following energy level diagram.

A reaction energy level diagram for an AN1 reaction. The rate-limiting step is spontaneous
dissociation of an alkyl halide to give a carbocation intermediate.

Answer the following questions:

i. In SN1 reaction the hybridization changes in the rate determination step, from ________ to ________.

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 ii. Select the correct statement(s) about the graph 1.
a. first step is rate-determining and it is endothermic
b. first step is rate-determining and it is exothermic
c. the second step is rate-determining and it is exothermic.
d. the second step is rate-determining and it is endothermic.
iii. Which is the rate-determining step in the graph 2? Tell whether the reaction is exothermic or
endothermic?
iv. In graph 3 for SN1 reaction the rate-limiting step is the spontaneous dissociation of alkyl halide

and is given by ________ step.

v. The SN1 reaction involves the formation of which intermediate?

57. Adolf von Baeyer suggested that, since carbon prefers to have tetrahedral geometry with bond angles
of approximately 109o, ring sizes other than five and six may be too strained to exist. Baeyer based
his hypothesis on the geometrical notion that a three-membered ring (cyclopropane) should be an

equilateral triangle with bond angles to 60o, a four-membered ring (cyclobutane) should be a square
with bond angles of 90o and so on. According to Baeyer's analysis, cyclopropane, with a bond angle

compression of 109o - 60o = 49o, should have a large amount of angle strain and must therefore, be
highly reactive. Cyclohexane becomes puckered to release its strain. The angular deviation of
cycloalkane is (-11o). Greater is the angular deviation more is the torsional strain.
Answer the following questions:
i. Which of the following is most reactive cycloalkane?
a. Cyclopropane
b. Cyclobutane
c. Cyclopentane
d. Cyclohexane
ii. Out of Cyclopropane, Cyclobutane and Cyclopentane are most strained cycloalkane?
iii. Write the tendency of Cyclopropane (I), Cyclobutane (II) and Cyclopentane (III) to form addition
compounds in the descending order.
iv. ________ has the greatest bond angle and zero strain energy. (Cyclohexane/Cyclobutane)
v. If the angular deviation is higher then what would be the effect on the torsional strain?
58. Bimolecular nucleophilic substitution (SN2) has four variable, i.e., substrate structure, nucleophile,

leaving group and solvent, Reaction energy level diagram for these factors are given in the following
diagrams:

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 Answer the following questions.
i. Steric hindrance raises the energy of the transition state, increasing ΔG and decreasing the
reaction rate. (True/False)
ii. How does more reactive nucleophile decrease the ΔG and increase the rate of reaction?
iii. Nueutral nucleophiles are ________ reactive than negatively charged nucleophiles.
iv. Good leaving groups, lower the energy of the transition staet, thus ________ ΔG and ________ the
reaction rate.
v. How does Protic solvent affect the ΔG and rate of reaction?
59. Hydrogenation of alkenes and alkynes takes place in presence of certain catalysts. In Sabatier
Senderen's reaction, the addition of hydrogen takes place in the presence of Raney nickel catalyst.
Platinum and Palladium can also be used as a catalyst in these reactions. These are the heterogeneous
catalyst and used in a finely divided state. Experimentally, it is observed that less crowded alkenes
adsorb H2 with a faster rate. Controlled hydrogenation of alkyne in the presence of Lindlar's catalyst
yields cis product i.e., 'cis' alkene. Thus, in the presence of Lindlar's catalyst, 'syn' addition takes place.
The relative rate of hydrogenation follows the order:

Non-terminal alkynes are reduced in the presence of Na or Li metal dissolved in liquid ammonia. In
this reaction, anti-addition of hydrogen results into the trans-product.
Answer the following questions:
i. Which type of alkenes adsorb H2 with faster rate?

ii. Out of CH3CH2CH2CH3 and . What is the product (A) for the following given

reaction?
Pd/CaCO3
C H3 − C ≡ C − C H3 + H2 (A)
 iling Quinoline 

iii. In which of the following cases, the reaction is most exothermic?

a.

b.

c.

d.

iv. Powdered nickel is more effective than the grannular nickel. Why?

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 v. In non-terminal alkynes reaction what products are formed?
60. Oxidation without cleavage of sigma bond takes place in alkenes:

Presence of unsaturation in alkenes is detected using Baeyer's reagent. Alkenes decolourise pink
colour of Baeyer's reagent. In the presence of Baeyer's reagent, syn addition of -OH groups takes place
on both carbons of the double bond. The next reaction can be given as,

Ozonolysis of alkenes gives ozonide, which on further hydrolysis gives aldehyde and/or ketone.

Answer the following questions:

i. Linear polyenes on ozonolysis give two moles of acetaldehyde and one mole of propane dial.
Linear polyene will be ________.
ii. Ortho xylene on ozonolysis will give ________.
O O O

|| || ||

(a) CH3 − C − C − C H3 and CH3 − C − CHO (b)

O O O

|| || ||

C H3 − C − C − C H3 , C H3 − C − CHO and CHO − CHO

iii. CH2=CH2 and CH3-CH=CH2 both will give formaldehyde on ozonolysis. (True/False)

iv. Product of ozonolysis gives information about:

a. configuration
b. conformation
c. both of these
d. none of these
v. Why would Bayer's Reagent is used for the detection of the alkene?

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