Solution

CHAPTER TEST

Class 11 - Chemistry

1. (a) Propene
Explanation: Elimination reaction takes place, a molecule of HBr gets eliminated to form propene.
2.
(c) HI > HBr > HCI
Explanation: HI > HBr > HCI
3. (a) 1,3-dimethylbenzene

Explanation:

4.
(d) Geometric isomers
Explanation: Isomers which have the same structural formulae but differ in the relative spatial arrangements of atoms or
groups around the double bond are called geometric isomers. Thus geometrical isomers are a type of stereoisomers.
5.
(d) HgSO4
Explanation: Alkynes are not readily hydrated due to their low reactivity towards electrophilic addition reactions.Further
dilute H2SO4 has no effect on carbon carbon triple bond.In the presence of HgSO4 as catalyst,hydration occurs readily.

6. (a) A mixture of low boiling hydrocarbons.

Explanation: Pyrolysis is the decomposition of a compound by the application of heat. It involves the breaking of C-C and C-
H bonds resulting in the formation of lower boiling alkanes.
7. (a) 3
Explanation: The position isomers of C5H8 are n-pentyne, 3-methyl butyne, pent-2-yne.

8. (a) CnH2n
Explanation: Alkenes are unsaturated hydrocarbons with at least on double bond between the carbon atoms. Their general
formula is CnH2n.

9.
(b) Sodium acetate
Explanation:
This is an example of Kolbe's electrolysis method. The reaction is:
electrolysis

2C H3 C OON a + 2H2 O ⟶ C H3 . C H3 + 2N aOH + H2 + 2C O2

The step-wise redox reactions occuring in the electrolytic cell are depicted as under

2H- → H2

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10.
(c)

Explanation: This is because geometrical isomerism is not possible if three groups are same.
11.

(b)

Explanation:
Aromaticity of a compound can be decided by Huckel’s rule. In cyclopentadienyl cation (b), resonance takes place as follows:

Hence,

is an anti-aromatic does not follow

Huckel’s rule as it has conjugated 4 π -electron (4nπ , n = 1) system. Rest of the species are aromatic as each of them belongs to
6π -electron [(4n + 2) π , n = 1] system.

12.
(c) CnH2n
Explanation: Cycloalkane with one benzene ring has a formula C6H12.
∴ The formula becomes CnH2n
Ni
CH2 = CH2 + H2 CH3 − CH3
13. 573K

Ethylene ethane

14. IUPAC name

i. 3, 5-dimethyl-2-hexene or 3, 5 -dimethylhex-2-ene
ii. 4-chloro-3-methylcyclopentene
iii. 1-sec-butyl-2-methylcyclohexene or 1-methyl-2-(1-methylpropyl) cyclohexen
iv. 2-pentyl-1-heptene or 2-pentylhept-1-ene
15. a. The struture of 2-methyl -3-isopropyl heptane is:

b. The struture of Dicyclopropyl methane is:

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16. i. Bromoethane when treated with zinc and hydrochloric acid, it is reduced to the Ethane.

ii. 2-Bromopropane is treated with hydrogen in the presence of palladium, Pd, propane is obtained as a major product.

17. With the increase in molecular weight or the molecular size of the molecule, the surface area of the molecule increases. Due to
which the extent of the intermolecular Vanderwall forces increases which causes the increase in the boiling point of alkanes.
18. Polymerization is the process of combining two or more monomeric units of unsaturated compounds under suitable conditions to
form a bigger compound, the compound formed is known as the polymer chains or three-dimensional networks.
Polymerization process has two types:
a. Addition polymerization
b. Condensation polymerization
For example

19. In methane carbon forms single bonds with four hydrogen atoms. Since the carbon atom is attached to four other atoms it uses sp3
hybrid orbitals to form these bonds.
Hybridization of 'C' is sp3

Shape-tetrahedral having bond angle = 109.5°

In ethane, there are six C-H covalent bonds and one C-C covalent bond.
The C-H bond is the result of overlap of an sp3 hybrid orbital from carbon and s-orbital from hydrogen.
Orbital structure can be shown as

20. According to given question, given alkene contains: three C—C, eight C—H, σ -bonds and one C—C π -bond. It is also given that,
Alkene (A), on ozonolysis gives two aldehyde having molar mass 44 u which is ethanal, CH3CHO. Now, writing the structures of
two molecules of ethanal in such a way that their oxygen atoms pointing towards each other. Join the two ends through the double
bond with the removal of both of the oxygen atoms to obtain alkene A.

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 Hence, alkene (A) is but-2-ene.
21. i. The stability of structural isomers generally increases with increasing branching. Thus,
Pentane [CH3(CH2)3CH3] < iso-pentane, [(CH3)2CH CH2CH3] < neo-pentane, [(CH3)4C]
ii. Method of preparation of propane from (a) an alkene (b) an alkyl halide.
Pt, Pd or Ni

a. CH 3 − CH = CH2 + H2 −−−−−−−→ CH3 − CH − CH3

Catalyst
Zn/HCI

b. CH 3 − CH2 − CH2 − CI −−−−−−→ CH3 − CH2 − CH3

or LiALIH4

iii. The alkenes must have the same carbon skeleton as 2-methyl butane.
C − C − C − C
|

There are three different positions for the double bond; hence the three different alkenes are
CH2 = C − CH2 − CH3 , CH3 − C = CHCH 3 , C H3 − CH − CH = CH2
| | |

CH3 CH3 CH3

iv. The Cl-Cl bond must be broken to form Cl radical before the reaction with methane. This homolysis requires energy, which is
supplied either by heat or light.

22.

The three compounds are isomers of molecular formula C6H14, n-hexane has the longest chain and has the highest boiling point.
2, 2-dimethylbutane is the most spherical and has the smallest surface area. In this case the van der waal’s force will be weakest
and has the lowest boiling point. Thus, the increasing order of boiling point of the three isomers follows.
2, 2-dimethylbutane < 3-methylpentane < n-hexane.

23. The basic skeleton 2-methyl butane is,

Putting double bonds at various different positions and satisfying the tetracovalency of each carbon, the structures of various
alkenes which give 2-methylbutane on hydrogenation are:

24. CH3, group is electron-donating while- NO2 group is electron-withdrawing. Therefore, maximum electron density will be in
toluene, followed by benzene and least in m-dinitrobenzene. Therefore, the ease of nitration decreases in the order:
toluene > benzene > m-dinitrobenzene.
25. i. In trans-but-2-ene, the dipole moments of the two C - CH3 bonds are equal and opposite and therefore, they cancel out each
other. Hence trans-2-butene is non-polar.

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 ii. a. cis-1, 2-dichloroethene

b. trans-1, 2-dichloroethene

c. 1, 1-dichloroethene

Out of these (b) is non-polar

4 3 2 1

26. i. C H 3 CH = C - C H3
|

CH3

2−Methylbut - 2 - ene

1 2 3 4 5

ii. C H 2 = CH − C = C − H
3

P ent−1−en−3y−ne

iii.

Buta-1,3-diene
iv.

v.

27. i.

The cis form will have a higher boiling point due to the more polar nature of the molecular leading to strong intermolecular
dipole-dipole interactions. As a result of stronger intermolecular interactions, it requires more energy to separate the
molecules.
ii. a. Z
b. Z
c. E
28. i. Pass the mixture through ammoniacal silver nitrate solution, propyne will precipitate out as silver propynide and propene will
pass unchanged.
+ − +
H3 C − C = C H + Ag → H3 C − C = C Ag
Pr ecipitate

H3C-CH=CH2 + Ag+ → No reaction

−
B2 H6 , H2 O2 ,OH

ii. a. H 3 C C H2 C H = C H2 −−−−−−−−−−→ C H3 C H2 C H2 OH
Alk.KMnO4

b. H 3C C H2 C H = C H2 −−−−−−−→ H3 C − C H2 − C H − C H2
| |

OH OH
H2 S O Re arrangement
4

c. H 3 CC = CH −−−−→ C H3 C H = C H2 −−−−−−−−−→ C H3 C C H3
2+ | ||
Hg
OH O

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 Zn

d. Br 2 C HC HBr2 −
−→ HC ≡ C H

29. i. Isomers of C4H8 having one double bond are

a.

b.

c.

d.

ii. Isomers of C5H8 having one triple bond are

a.

b.

c.

30. i. Addition of HBr to propene is an ionic electrophilic addition reaction which follows Markonikov rule. In this case H+ adds to
alkene to give a more stable 2 carbocation. This is rapidly attacked by nucleophile Br- ion to give 2-bromo propane.
∘

+
CH3 − CH − CH3
Slow

CH3 - CH = CH2 + H+ −−−→ ∘

2 − Carbocation

(more stable)

CH3 − CH − CH3
Fast

CH3 - CH+ - CH3 + Br- −−→ Br

2 − Bromopropane
∙

In the presence of benzoyl peroxide, the reaction follows free radical addition. In this case Br free radical acts as electrophile
which is obtained from the action of benzoyl peroxide on HBr.
˙
2C6 H5 COO ⟶ 2C6 H5 + 2CO2
Homolytic f ission

C6 H5 C O − O − O − C O C6 H5 −−−−−−−−−−→ Phenyl free

Heat
radical

˙
C6 H5 + HBr ⟶ C6 H6 + Br
Benzene

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 ∙

Br free radical attacks propene in such a way to generate a more stable 2 free radical. This free radical obtained rapidly
∘

abstracts a hydrogen atom of BHr to give 1-Bromopropane.

CH3 − CH − CH2 Br
Slow
˙ ∘
CH3 − CH = CH2 + Br ⟶ 2 − Free radical

(stable)
∙
Fast
∙
CH3 CH2 CH2 Br + Br
CH3 − CH − CH2 Br + H − Br −−→
1 − Bromopropane

ii. o-xylene may be regarded as a resonance hybrid of the following structures. Ozonolysis of each one of these gives
two products shows as ahead:

Therefore, only three products are formed. Since all the three profucts cannot be obtained from any one of the two Kekule
structures, this shows that o-xylene is a resonance hybrid of two Kekule structures (I) and (II).

31. (a) Both A and R are true and R is the correct explanation of A.
Explanation: Both A and R are true and R is the correct explanation of A.
32.
(c) A is true but R is false.
Explanation: Among isomeric pentanes 2, 2-dimethylpentane has the lowest boiling point and on branching, the boiling point
decreases.
33.
(b) Both A and R are true but R is not the correct explanation of A.
Explanation: Both A and R are true but R is not the correct explanation of A.
34.
(b) Both A and R are true but R is not the correct explanation of A.
Explanation: Both A and R are true but R is not the correct explanation of A.
35. Experimentally, it is observed that less crowded alkenes adsorb H2 with the faster rate.

36. The product (A) formed is .

37. Powdered nickel is more effective than the grannular nickel because the surface area of powdered nickel is maximum and Free
valencies are large in number.
38. In non-terminal alkynes reaction, anti-addition of hydrogen results into the trans-product.
39. Resonance energy: The difference between the energy of the most stable contributing structure and the energy of the resonance
hybrid is known as resonance energy. Example: The resonance energy of benzene is 147KJ/mole.
40. In case of methane, each H atom has an equal share of the electrons bonding them to the C atom and are formed by the
overlapping of the same type of orbital i.e., hybrid orbital’s of carbon and s-orbital of hydrogen. This means all four H atoms that
are separated from each other by the same angle and separated from the C atom by the same distance. Hence, all the C-H bonds in
methane are identical to one another.
41. It is due to the smaller size C-C bond which is stronger (335 KJ mol-1) than in Si bond (225.7 KJ mol-1).
42. Ethyne is the simplest alkyne. Formula of ethyne is C2H2.
Structure: H − C ≡ C − H

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