13.

HYDROCARBONS

Chemistry Smart Booklet

Theory + NCERT MCQs + Topic Wise Practice
MCQs + NEET PYQs

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 HYDROCARBONS

Introduction
The term ‘hydrocarbon’ is self-explanatory meaning compounds of carbon and hydrogen
only. Hydrocarbons hold economic potential in our daily life. Natural gas and petroleum
are chief sources of aliphatic hydrocarbons at the present time, and coal is one of the major
sources of aromatic hydrocarbons. Petroleum is a dark, viscous mixture of many organic
compounds, most of them being hydrocarbons, mainly alkanes, cycloalkanes and
aromatic hydrocarbons.

Classification
As we are quite aware that there are different types of hydrocarbons. Depending upon the
types of carbon-carbon bonds present, they can be classified into three main categories:
1. Saturated hydrocarbons.
2. Unsaturated hydrocarbons.
3. Aromatic hydrocarbons.
Saturated hydrocarbons contain carbon-carbon and carbon-hydrogen single bonds. If
different carbon atoms are joined together to form open chain of carbon atoms with single
bonds, they are termed as alkanes. On the other hand, if carbon atoms form a closed chain
or ring, they are termed as cycloalkanes. Unsaturated hydrocarbons contain carbon-
carbon multiple bonds – double bonds, triple bonds or both. Aromatic hydrocarbons are
a special type of cyclic compounds.

ALKANES
These are the saturated chains of hydrocarbons containing carbon-carbon single bonds.
Methane (CH4) is the first member of this family containing single carbon atom. Since it is
found in coal mines and marshy areas, is also known as ‘marsh gas’. These hydrocarbons
exhibited low reactivity or no reactivity under normal conditions with acids, bases and
other reagents, they were earlier known as paraffins. The general formula for alkane is
CnH2n + 2, where n stands for number of hydrogen atoms in the molecule.

Structure of Methane

1. Nomenclature

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For nomenclature of alkanes in IUPAC system, the longest chain of carbon atoms
containing the single bond is selected. Numbering of the chain is done from the one end
so that maximum carbon will be included in chain. The suffix ‘ane’ is used for alkanes.
The first member of the alkane series is CH4 known as methylene (common name) or
methene (IUPAC name). IUPAC names of a few members of alkenes are given below:

S. No. Structure IUPAC Name

1. CH4 Methane
2. C2H6 Ethane
3. C3H8 Propane
4. C4H10 Butane
5. C5H12 Pentane
6. C6H14 Hexane
7. C7H16 Heptane
8. C8H18 Octane
9. C9H20 Nonane
10. C10H22 Decane

2. Preparation of Alkanes
Though petroleum and natural gas are the main sources of alkanes, it can be prepared by
several other methods as well.

i. From unsaturated hydrocarbons: The addition of dihydrogen to unsaturated

hydrocarbons like alkenes and alkynes in the presence of a suitable catalyst under a
given set of conditions produces saturated hydrocarbons or alkanes. This process of
addition of dihydrogen is known as hydrogenation process.
CH2＝CH2 + H2 ⟶ CH3-CH3

CH☰CH + 2H2 ⟶ CH3-CH3

ii. From alkyl halides

a) Reduction: Alkyl halides undergo reduction with zinc and dilute hydrochloric acid
to give alkanes. In general, the reaction can be represented as
CH3-Cl ⟶ CH4

b) Wurtz reaction: Alkyl halides on treatment with sodium metal in dry ether give
higher alkanes. This reaction is known as Wurtz reaction.
CH3Br + 2Na + BrCH3 ⟶ CH3-CH3 + 2NaBr

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iii. From carboxylic acids
a) By decarboxylation of carboxylic acids: Sodium salts of carboxylic acids on
heating with soda lime give alkanes containing one carbon atom less than the
carboxylic acid. A molecule of carbon dioxide is eliminated which dissolves in
NaOH to form sodium carbonate.
CH3COONa + NaOH ⟶ CH4 + Na2CO3

b) Kolbe’s electrolytic method: An aqueous solution of sodium or potassium salt of

a carboxylic acid on electrolysis gives alkane containing even number of carbon
atoms at anode.
CH3COONa + 2H2O ⟶ CH3-CH3 + 2CO2 + H2 + NaOH

3. Properties of Alkanes
I. Physical Properties
i. State: Due to the weak van der Waals forces, the first four members C1 to C4 i.e.,
methane, ethane, propane and butane are gases. From C5 to C17 are liquids and
those containing 18 carbon atoms or more are solids at 298 K. They all are colourless
and odourless.
ii. Solubility: Alkanes are generally insoluble in water or in polar solvents, but they are
soluble in non-polar solvents like, ether, benzene, carbontetrachloride etc. The
solubility of alkanes follow the property “Like Dissolves like”.
iii. Boiling point: The boiling points of straight chain alkanes increase regularly with
the increase of number of carbon atoms. This is due to the fact that the intermolecular
van der Waals forces increase with increase in the molecular size or the surface area
of the molecule.
II. Chemical Properties
Generally, alkanes show inertness or low reactivity towards acids, bases, oxidizing and
reducing agents at ordinary conditions because of their non-polar nature and absence of
π bond. The C–C and C–H bonds are strong sigma bonds which do not break under
ordinary conditions but they undergo certain reactions under given suitable conditions.

i. Halogenation reaction: When hydrogen atom of an alkane is replaced by a halogen,

it is known as halogenation reaction. Halogenation takes place either at high
temperature (300–500°C) or in the presence of diffused sunlight or ultraviolet light.
CH4 + Cl2 ⟶ CH3Cl + HCl

ii. Combustion: Alkanes on heating in presence of air gets completely oxidized to

carbon dioxide and water. It burns with a non-luminous flame. The combustion of
alkanes is an exothermic process i.e., it produces a large amount of heat.
CH4 + 2O2 ⟶ CO2 + 2H2O

iii. Controlled oxidation: When methane and dioxygen compressed at 100 atm are
passed through heated copper tube at 523K yield methanol.
2CH4 + O2 ⟶ 2CH3OH

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 iv. Aromatization: The conversion of aliphatic compounds into aromatic compounds is
known as aromatisation. n-Alkanes having six or more carbon atoms on heating to
773K at 10–20 atmospheric pressure in the presence of oxides of vanadium,
molybdenum or chromium supported over alumina get dehydrogenated and
cyclised to benzene and its homologues. This reaction is also known as reforming.

v. Reaction with steam: Methane reacts with steam at 1273K in the presence of nickel
catalyst to form carbon monoxide and dihydrogen. This method is used for
industrial preparation of dihydrogen gas.
CH4 + H2O ⟶ CO + 3H2

ALKENES

Alkenes are unsaturated hydrocarbons containing at least one carbon-carbon double bond
with general formula CnH2n. Alkenes are also known as olefins (oil forming) since the
first member, ethylene or ethene (C2H4) was found to form an oily liquid on reaction with
chlorine.

1. Nomenclature

For nomenclature of alkenes in IUPAC system, the longest chain of carbon atoms
containing the double bond is selected. Numbering of the chain is done from the end
which is nearer to the double bond. The suffix ‘ene’ replaces ‘ane’ of alkanes. The first
member of the alkene series is C2H4 known as ethylene (common name) or ethene
(IUPAC name). IUPAC names of a few members of alkenes are given below:

S.No. Structure IUPAC Name

1. C2H4 Ethene
2. C3H6 Propene
3. C4H8 Butene
4. C5H10 Pentene
5. C6H12 Hexene
6. C7H14 Heptene
7. C8H16 Octene
8. C9H18 Nonene
9. C10H20 Dekene

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2. Preparation

i. From alkynes: Alkynes undergo partial reduction with calculated amount of

dihydrogen producing alkenes.

CH☰CH + H2 ⟶ CH2＝CH2

ii. From alkyl halides: Alkyl halides (R–X) on heating with alcoholic potash eliminates
one molecule of halogen acid to form alkenes. This reaction is known as
dehydrohalogenation i.e., removal of halogen acid.

CH3CH2Cl ⟶ CH2＝CH2 + HCl

iii. From alcohols by acidic dehydration: Alcohols on heating with concentrated

sulphuric acid form alkenes with the elimination of one water molecule since a water
molecule is eliminated from the alcohol molecule in the presence of an acid, this
reaction is known as acidic dehydration of alcohols.

CH3CH2OH ⟶ CH2＝CH2 + H2O

3. Properties of Alkenes

I. Physical properties

i. The first three members of alkenes are gases, the next fourteen are liquids and the
higher ones are solids.

ii. Ethene is a colourless gas with a faint sweet smell. All other alkenes are colourless
and odourless, insoluble in water but fairly soluble in non-polar solvents like
benzene, petroleum ether.

iii. They show a regular increase in boiling point with increase in size i.e., every —
CH2 group added increase the boiling point by 20–30K.

II. Chemical properties

i. Addition of dihydrogen: Alkenes adds one mole of dihydrogen gas in presence

of catalysts such as Ni at 200–250°C, or finely divided Pt or Pd at room
temperature to give an alkane.

CH2＝CH2 + H-H ⟶ CH3-CH3

ii. Addition of halogens: Halogens like bromine or chlorine add up to alkene to form
vicinal dihalides in presence of CCl4 as solvent. The order of reactivity of halogens
is F > Cl > Br > I.

CH2＝CH2 + Br-Br ⟶ Br-CH2-CH2-Br

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 iii. Addition of hydrogen halides: Hydrogen halides (HCl, HBr, HI) add upto
alkenes to form alkyl halides. The order of reactivity of hydrogen halides is HI >
HBr > HCl. Like addition of halogens to alkenes, addition of hydrogen halides is
an example of electrophilic addition reaction.

CH2＝CH2 + H-Br ⟶ CH3-CH2-Br

Markovnikov rule: According to the rule, the negative part of the addendum
(adding molecule) adds to that carbon atom of the unsymmetrical alkene which is
maximum substituted or which possesses lesser number of hydrogen atoms.

CH3CH＝CH2 + HBr ⟶ CH3-CH(Br)-CH3

Anti Markovnikov addition or Peroxide effect or Kharash effect: In the presence

of peroxide, addition of HBr to unsymmetrical alkenes like propene takes place
contrary to the Markovnikov rule. This happens only with HBr but not with HCl
or HI. This reaction is known as peroxide or Kharash effect or addition reaction
anti to Markovnikov rule.

CH3CH＝CH2 + HBr ⟶ CH3-CH2-CH2-Br

iv. Polymerisation: Polymerisation is the process where monomers combines
together to form polymers. The large molecules thus obtained are called polymers.
Other alkenes also undergo polymerisation.

n(CH2＝CH2) ⟶ (-CH2-CH2-)n

Alkenes

Like alkenes, alkynes are also unsaturated hydrocarbons with general formula C nH2n – 2.
They contain at least one triple bond between two carbon atoms. These have four H-atoms
less compared to alkanes. The first stable member of alkyne series is ethyne commonly
known as acetylenes.

1. Nomenclature
In common system, alkynes are named as derivatives of acetylene. In IUPAC system, they
are named as derivatives of the corresponding alkanes replacing ‘ane’ by the suffix ‘yne’.
The position of the triple bond is indicated by the first triply bonded carbon. Common
and IUPAC names of a few members of alkyne series are given in the table below:

S.No. Structure IUPAC Name

1. C2H2 Ethyne
2. C3H4 Propyne
3. C4H6 Butyne
4. C5H8 Pentyne
5. C6H10 Hexyne

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2. Preparation

i. From calcium carbide: On industrial scale, ethyne is prepared by reacting calcium

carbide with water. Calcium carbide is prepared by heating quick lime with coke.
Quick lime can be obtained by heating limestone as shown in the following reactions:

CaCO3 ⟶ CaO + CO2

CaO + 3C ⟶ CaC2 + CO

CaC2 + 2H2O ⟶ Ca(OH)2 + C2H2

ii. From vicinal dihalides: Vicinal dihalides on treatment with alcoholic potassium
hydroxide undergo dehydrohalogenation. One molecule of hydrogen halide is
eliminated to form alkenyl halide which on treatment with sodamide gives alkyne.

CH2(Br)-CH2(Br) + KOH ⟶ CH2＝CH2 ⟶ CH☰CH

4. Properties of Alkenes

I. Physical properties

i. The first three members (acetylene, propyne and butynes) are gases, the next eight
are liquids and higher ones are solids.
ii. All alkynes are colourless. All alkynes except ethyne which have an offensive
characteristic odour, are odourless.
iii. Alkynes are weakly polar in nature and nearly insoluble in water. They are quite
soluble in organic solvents like ethers, carbon tetrachloride and benzene.
iv. Their melting point, boiling point and density increase with increase in molar
mass.

II. Chemical properties

i. Addition of dihydrogen: Alkynes contain a triple bond, so they add up, two
molecules of dihydrogen.

CH☰CH + H2 ⟶ CH2＝CH2 ⟶ CH3-CH3

ii. Addition of halogens: Alkynes contain a triple bond, so they add up, two
molecules of halogen.

CH☰CH + Cl2 ⟶ CH(Cl)＝CH(Cl) ⟶ CH(Cl)2-CH(Cl)2

iii. Addition of hydrogen halides: Two molecules of hydrogen halides (HCl, HBr,
HI) add to alkynes to form gemdihalides (in which two halogens are attached to
the same carbon atom).

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 CH☰CH + HCl ⟶ CH2＝CH(Cl)

iv. Addition of water: Like alkanes and alkenes, alkynes are also immiscible and do
not react with water. However, one molecule of water adds to alkynes on
warming with mercuric sulphate and dilute sulphuric acid at 333K to form
carbonyl compounds.

CH☰CH + H2O ⟶ CH3-CHO

v. Polymerisation: Ethyne on passing through red hot iron tube at 873K undergoes
cyclic polymerization. Three molecules polymerise to form benzene, which is the
starting molecule for the preparation of derivatives of benzene, dyes, drugs and
large number of organic compounds.

vi. Oxidation:

2C2H2 + 5O2 ⟶ 4CO2 + 2H2O

Aromatic Hydrocarbon

Aromatic hydrocarbons are also known as ‘arenes’. Since most of them possess pleasant
odour (Greek; aroma meaning pleasant smelling), the class of compounds are known as
‘aromatic compounds’. Most of the compounds are found to have benzene ring. Benzene
ring is highly unsaturated and in a majority of reactions of aromatic compounds, the
unsaturation of benzene ring is retained. Aromatic compounds containing benzene ring
are known as benzenoids and those, not containing a benzene ring are known as non-
benzenoids.

1. Nomenclature
Since all the six hydrogen atoms in benzene are equivalent; so it forms one and only one
type of monosubstituted product. When two hydrogen atoms in benzene are replaced by
two similar or different monovalent atoms or groups, three different position isomers are
possible which differ in the position of substituents. So we can say that disubstituted
products of benzene show position isomerism. The three isomers obtained are 1, 2 or 1, 6
which is known as the ortho (o-), the 1, 3 or 1, 5 as meta (m-) and 1, 4 as para (p-)
disubstitued compounds.

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2. Structure
The molecular formula of benzene, C6H6, indicates a high degree of unsaturation. All the
six carbon and six hydrogen atoms of benzene are identical. On the basis of this
observation August Kekule in 1865 proposed the following structure for benzene having
cyclic arrangement of six carbon atoms:

3. Resonance
Even though the double bonds keep on changing their positions. The structures
produced is such that the position of nucleus remains the same in each of the structure.
The structural formula of such a compound is somewhat intermediate (hybrid) between
the various propose formulae. This state is known as Resonance.

4. Preparation of Benzene
i. Cyclic polymerisation of ethyne: Ethyne on passing through red hot iron tube at
873K undergoes cyclic polymerization.

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 ii. Decarboxylation of aromatic acids: Sodium salt of benzoic acid i.e., sodium
benzoate on heating with sodalime gives benzene.

iii. Decarboxylation of aromatic acids: Sodium salt of benzoic acid i.e., sodium
benzoate on heating with sodalime gives benzene.

iv. Reduction of phenol: Phenol is reduced to benzene by passing its vapour over
heated zinc dust.

5. Properties of Benzene

I. Physical Properties

i. Aromatic hydrocarbons are non-polar molecules and are usually colourless

liquids or solids with a characteristic aroma.
ii. The napthalene balls used in toilets and for preservation of clothes because of
unique smell of the compound.
iii. Aromatic compounds are insoluble in water but soluble in organic solvents such
as alcohol and ether.

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 iv. They burn with sooty flame.

II. Chemical properties

i. Nitration: A nitro group is introduced into the benzene ring when benzene is
heated with a mixture of concentrated nitric acid and concentrated sulphuric acid.

ii. Halogenation: Arenes undergo halogenation when it is treated with halogens in

presence of Lewis catalyst such as anhy. FeCl3, FeBr3 or AlCl3 to yield haloarenes.

iii. Sulphonation: The replacement of a hydrogen atom by a sulphonic acid group in

a ring is called sulphonation. It is carried out by heating benzene with fuming
sulphuric acid or oleum (conc. H2SO4 + SO3).

iv. Friedel-Crafts alkylation reaction: When benzene is treated with an alkyl halide
in the presence of anhydrous aluminium chloride, alkylbenzene is formed.

Activating Groups: Electron donating groups (EDG, +M, +I, +H. C. effect) in the
benzene ring will more stabilize the σ-complex (Arenium ion complex) with
respect to that of benzene and hence they are known as activator.

Deactivating Groups: Electron drawing groups (–M, –I effects) will destabilize

σ-complex as compared to that of benzene. Therefore substituted benzenes
where substituents are electron withdrawing decreases reactivity towards SE
reactions.

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Summary-

1. Hydrocarbons: The compounds which are made up of only carbon and hydrogen
elements.
2. LPG (Liquefied petroleum gas), LNG (Liquefied natural gas) and CNG (Compressed
natural gas) are important fuels.
3. Alkanes are saturated hydrocarbons having general formula CnH2n+2. They contain
only C—C and C—H sigma bonds.
4. Alkenes are unsaturated hydrocarbons having general formula CnH2n. They contain
a carbon-carbon double bond.
5. Alkynes are unsaturated hydrocarbons having general formula CnH2n–2. They contain
a carbon-carbon triple bond.
6. Alkanes exhibit conformational isomerism due to almost free rotation about C—C
sigma bond.
7. Alkenes exhibit geometric isomerism due to restricted rotation about carbon-carbon
double bond.
8. The cis isomer is more polar and has higher boiling point than the trans isomer. On
the other hand the melting point of trans isomer is higher.
9. Cracking: The process of decomposing higher hydrocarbons into lower
hydrocarbons by strong heating.
10. Reforming or Aromatisation: The process of converting aliphatic and alicyclic
hydrocarbons into aromatic hydrocarbons by heating in the presence of suitable
catalysts such as platinum.
11. Grignard reagent: RMgX, Alkyl magnesium halide.
12. Soda-lime decarboxylation of sodium salts of carboxylic acids leads to formation of
alkane with one carbon less than the starting compound.
13. Dehydrohalogenation of Alkyl halides is carried out by heating with alcoholic
solution of KOH.
14. Branched chain hydrocarbons have lower boiling points than straight chain
hydrocarbons having same number of carbon atoms.
15. Among isomeric xylenes, para isomer has the highest melting point.
16. Baeyer’s reagent: 1% cold and alkaline solution of KMnO4.
17. Markovnikov’s rule: During electrophilic addition across unsymmetrical double
bond, the negative part of the adding molecule goes to that carbon which has less
number of hydrogen atoms.
18. Kharash effect: Anti-Markovnikov addition of HBr to alkenes in the presence of
organic peroxides.

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19. Arenes are aromatic hydrocarbons. They contain at least one benzene ring.
20. The important reactions of alkanes are free radical substitution reactions while that
of alkenes and alkynes are electrophilic addition reactions.
21. Aromatic hydrocarbons are undergo mainly electrophilic substitution reactions
inspire of high degree of unsaturation present in them.
22. Aromaticity in aromatic compounds is due to the presence cyclic, delocalized system
of (4n+2) π electrons.
23. Substitution reactions are common for alkanes and arenes whereas addition
reactions are common for alkenes and alkynes.
24. The catalyst for Friedel-Craft reaction is anhydrous AlCl3.
25. Terminal alkynes are acidic in character.
26. Electron releasing groups increase the reactivity of benzene ring towards
electrophilic substitution reactions. Some examples are —R, —OH, —NH2, —OR, —
NHCOCH3, etc.

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 NCERT LINE BY LINE QUESTIONS
(1.) A Compound is treated with NaNH 2 to give sodium salt. Identify the compound. [Page: 394]
(a.) C2H 2 (b.) C6 H 6
(c.) C2H 6 (d.) C2H 4

(2.) Which of the following has zero dipole moment [Page: 387]
(a.) 1‐Butene (b.) 2‐Methyl‐l‐Propene
(c.) Cis‐2‐Burene (d.) trans‐2‐Butene

(3.) Which of the following chemical system is non‐ aromatic [Page: 399]

(a.) (b.)

(c.) (d.)

(4.) Which of the following species are anti‐aromatic . [Page: 399]

(a.) I, II (b.) II, III

(c.) I, IV (d.) II, IV

(5.) Cis‐2‐butene and trans‐2‐butene are [Page: 386]

(a.) Conformational Isomers (b.) Structural Isomers
(c.) Configurational Isomers (d.) Optical Isomers

(6.) Which one is the correct order of acidity? [NEET‐2017, Page: 394]
(a.) CH  CH  CH3  C  CH  CH 2  CH 2  CH3  CH3
(b.) CH  CH  CH 2  CH 2  CH3  C  CH  CH3  CH3
(c.) CH3  CH3  CH 2  CH 2  CH3  C  CH  CH  CH
(d.) CH 2  CH 2  CH3  CH  CH 2  CH3  C  CH  CH  CH

(7.) Propene on reaction with chlorine water gives [Page: 389]

(a.) (b.)

(c.) (d.)

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(8.) Assertion (A): Alkyl benzene is not prepared by Friedel‐Craft alkylation of benzene.
Reason (R): Alkyl halides are less reactive than 1 acyl halides [Page: 402]
(a.) Both A and R are true and R is the correct (b.) Both A and R are true but R is nor the correct
explanation of A. explanation of A.
(c.) A is true but R is false. (d.) Both A and R are false.

(9.) The most suitable reagent for following conversion is: [NEET‐2019, Page: 387]

(a.) Na / liq.NH3 (b.) H 2 ,pd / c,quinoline

(c.) Zn / HCl (d.) Hg 2 / H  , H 2O

(10.) Which among the following is not aromatic) [Page: 399]

(a.) Cyclopemadienyl cation (b.) Cyclopropenyl cation
(c.) Tropylium cation (d.) Cyclopentadienyl anion

(11.) Which of the following can be used as the halide component for Friedel‐Craft’s reaction [Page: 40l]
(a.) Chlorobenzene (b.) Bromobenzene
(c.) Chloromethane (d.) Isopropyl Chloride

(12.) General formula of alkyne is [Page: 392]

(a.) C n H 2n (b.) Cn H 2n 1
(c.) Cn H 2n 2 (d.) Cn H 2n 2

(13.) Alkynes can be reduced to alkenes by the hydrogenation in presence of [Page: 395]
(a.) Raney Ni (b.) Anhyd. AICl3
(c.) Pd (d.) Lindlar’s Catalyst

(14.) The major product formed on monobromination  Br2 / FeBr3  of the following compound P [Page: 400]

(a.)
(b.)

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(c.) (d.)

(15.) Aromatisation can takes place in presence of [Page: 382]

(a.) Cr2O3 (b.) V2O5
(c.) Mo2O3 (d.) all (a.), (b) and (c)

(16.) Matrix Match [NCERT Exemplar, Page: 391]

Column 1 Column 2
 A  CH 2  CH 2  H 2 O 

H
CH3 CH 2 OH  P  Halogenation
 B CH 2  CH 2  H 2  Pd
 CH3  CH3  Q  Polymerisation
 C  CH 2  CH 2  C12  Cl  CH 2  CH 2  Cl  R  Hydrogenation
 D  3CH  CH  Cu tube
Heat
 C6 H 6 S Condensation
 T  Hydration
(a.) A  P, B  R, C  T, D  Q (b.) A → R, B →P, C →T, D →S
(c.) A  T, B  R, C  Q, D  P (d.) A  T, B  R, C  P, D  Q

(17.) The pair of electrons in the given carbanion, CH 3C  C , is present in which of the following orbitals
[HOT, Page: 394]
(a.) sp 2 (b.) sp
(c.) 2p (d.) sp3

 C H CO
(18.) The main product of the following reaction is CH3CH  CH2  HBr  
6 5 2 2
O

(a.) CH3CH  Br   CH3 (b.) CH3CH 2CH 2Br

(c.) BrCH 2  CH  CH 2
(d.)

(19.) Which of the compound with molecular formula C5H10 fields acetone on ozonolysis [Page: 391]
(a.) 3‐methyl‐1‐butene (b.) Cyclopentane
(c.) 2‐methyl‐1‐butene (d.) 2‐methyl‐2‐butene

(20.) In the following reaction [Page: 40l] C6 H 6  

CH3Cl / AlCl3
 P KMnO
 4
Q Here Q is
(a.) Benzoic Acid (b.) Benzoyl Chloride
(c.) Benzaldehyde (d.) Chlorobenzene

(21.) Which of the following statements are correct [Page: 382] (i) Decomposition reaction of higher alkane
into smaller fragments by the application of heat is called pyrolysis. (ii) Pyrolysis and cracking are
different processes. (iii) Dodecane on pyrolysis gives a mixture of heptane and pentene. (iv) Pyrolysis
follows free radical mechanism.

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(a.) (i), (ii), (iii) (b.) (i)2 (ii), (iv)
(c.) (i), (iii), (iv) (d.) (ii), (iv)

(22.) 2‐Hexyne gives trans‐2‐hexene on treatment with [Page: 394]

(a.) Li / NH 3 (b.) Pd / BaSO4
(c.) LiAlH 4 (d.) Pt / H 2

(23.) Which of the following compounds shall not produce propene by reaction with HBr followed by the
elimination or direct only elimination reaction . [NEET 2016, Page: 389]
(b.) H3C  CH 2  CH 2OH

(a.)
(c.) H 2C  C  O (d.) H3C  CH 2  CH 2Br

(24.) In the reaction with HCl, an alkene reacts in accordance with Markovnikov’s rules to give a product 1‐
chloro‐l‐methylcyclohexane. The possible alkene is ? [Page: 389]

(a.) (b.)
(c.) Both a and b

(d.)

(25.) Consider the nitration of benzene using mixed conc. H 2SO4 and HNO3 . If a large amount of KHSO4 is
added to the mixture, the rate of nitration will be: [Page: 400]
(a.) Double (b.) F aster
(c.) Slower (d.) Unchanged

(26.) Consider the following sequence of reactions [Page: 393] CaC2 

H2O
X Red
 hot
Fe tube
Y The Product Y is
(a.) Acetylene (b.) Benzene
(c.) Mesitylene (d.) Xylene

(27.) Assertion (A): The compound cyclooctane has the following structural formula. [NCERT Exemplar,

Page: 399] It is cyclic and has conjugated 8π  e system but it is not an aromatic
compound.
Reason (R):  4n  2 π electrons rule does not hold good and the ring is not planar. [NCERT Exemplar,
Page: 399]
(a.) Both A and R are true and R is the correct (b.) Both A and R are true but R is not the correct
explanation of A. explanation of A.
(c.) A is true but R is false. (d.) Both A and R are false.

19
(28.) Given [NEET‐2015]

(I)(II)(III)
The enthalpy of the hydrogenation of these compounds will be in the order as:
(a.) III  II  I (b.) II  III  I
(c.) II  I  III (d.) I  II  III

(29.) Which of the following reaction is shown by alkynes [Page: 394]

(a.) Addition (b.) Substitution
(c.) Polymerisation (d.) All of these

(30.) When acetylene is passed over heated iron tube, the product obtained is [Page: 393]
(a.) C2H 2 (b.) C4H 4
(c.) C6 H 6 (d.) C8 H 8

(31.) Predict wrong option for stability [Page: 387]

(a.) 2,3‐Dimethylbut‐2‐ene  2‐Methylpent‐2‐ene (b.) trans‐Hex‐3‐ene  Cis‐Hex‐3‐ene
(c.) cis‐Hex‐3‐ene  Hex‐l‐ene (d.) trans‐Hex‐2‐ene  2‐Methylpent‐2‐ene

(32.) Assertion (A): Benzene does not decolorise Br2 water.

Reason (R): Benzene is stabilised by resonance due to delocalisation of π ‐electrons. [Page: 400]
(a.) Both A and R are true and R is the correct (b.) Both A and R are true but R is not the correct
explanation of A. explanation of A.
(c.) A is true but R is false. (d.) Both A and R are false.

(33.) Benzene can be directly obtained from [Page: 400]

(a.) Acetylene (b.) Phenol
(c.) Chlorobenzene (d.) All of the Above

(34.) The number of  (Sigma) and  (Pie) bonds in benzene is [Page: 385]
(a.) 6 and 6π (b.) 6 and 3π
(c.) 12 and 3π (d.) 3 and 3π

(35.) Assertion (A): Acidity of C —H bond decreases in the order of. HC  CH  H 2C  CH 2  CH3  CH3.
Reason (R): Acidity of C —H bond increases as the electronegativity of the carbon to which it is attached
increases. [Page: 394]
(a.) Both A and R are true and R is the correct (b.) Both A and R are true but R is not the correct
explanation of A. explanation of A.
(c.) A is true but R is false. (d.) Both A and R are false.

(36.) 2‐Butene shows geometrical isomerism due to [Page: 386]

(a.) restricted rotation about double bond. (b.) free rotation about double bond.

20
(c.) free rotation about single bond. (d.) chiral carbon.

(37.) What products are formed when the following compound is treated with Br2 in the presence of FeBr3 ?

[NEET‐2014, Page: 400]

(b.)
(a.)

(d.)
(c.)

(38.) Count the  and π bonds in the following structure [Page: 385] H2C  C  CH2CH2CH3 2
(a.) 26 and 0π (b.) 19 and 1π
(c.) 18 and 1π (d.) 23 and 1π

(39.) Which of the following will have fastest rate of reaction with Br2 / FeBr3 . [Page: 400]

(a.) (b.)

(c.) (d.)

(40.) Among the following the aromatic compound is [Page: 399]

(a.)
(b.)

(c.)
(d.)

(41.) An alkene ‘A’ on reaction with O 3 and Zn  H 2O gives propanone and ethanal in equimolar ratio.
Addition of HCl to alkene ‘A’ gives ‘B’ as the major product. The structure of ‘B’ is [NEET‐2019, Page:
391]

21
 (b.)
(a.)

(c.) (d.)

(42.) Which of the following reagent will be able to distinguish between 1‐butyne and 2‐butyne . [Page: 394]
(a.) NaNH 2 (b.) HCl
(c.) O2 (d.) Br2

(43.) In which of the following reactions, addition does not occur according to Markovnikov’s rule [Page:
389]
(a.) CH 3CH  CH 2  HCl 
ROOR
 (b.) CH3CH  CH 2  HBr 
ROOR

(c.) CH 2  CH 2  HI 
ROOR
 (d.) CH 3CH  CHCH 3  HBr 
ROOR


(44.) Which of the following alkenes will react faster with H 2 under catalytic hydrogenation conditions?
[Page: 387]
(a.) C  C (b.) C  C
(c.) C  C (d.) C  C

(45.) For an electrophilic substitution reaction, the presence of a halogen atom in the benzene ring [Page: 402]
(a.) deactivates the ring by resonance. (b.) directs the incoming electrophile to meta
position by increasing the charge density
relative to ortho a para position.
(c.) Activates the ring by inductive effect. (d.) deactivates the ring by inductive effect.

(46.) Benzene reacts with I 2 in presence of which of the following to give iodobenzene? [Page: 400]
(a.) HNO3 (b.) HI
(c.) SO 2 (d.) H 2O

(47.) Which among the following alkenes on ozonolysis give a mixture of ketone only . [Page: 391]
(a.) CH3  CH  CH  CH3

(b.)

(c.) (d.)

(48.) Catalytic hydrogenation of benzene gives [Page: 400]

(a.) Xylene (b.) Cyclohexane
(c.) Benzoic Acid (d.) Toulene

22
 (49.) A gas decolourises alkaline KMnO4 solution but does not give precipitate with AgNO3 . It is [Page: 394]
(a.) CH 4 (b.) C2H 4
(c.) C2H 2 (d.) C2H 6

(50.) Alkenes usually show which type of reaction [Page: 384]

(a.) Substitution (b.) Addition
(c.) Elimination (d.) None of these

TOPIC WISE PRACTICE QUESTIONS

TOPIC 1: Alkanes
1. Pure methane can be produced by
1) Wurtz reaction 2) Kolbe’s electrolytic method
3) Soda-lime decarboxylation 4) Reduction with H2
2. In the eclipsed conformation of ethane, the dihedral angle between the hydrogen atoms of adjacent
methyl groups is
1) 60° 2) 120° 3) 0° 4) 180°
3. Photochemical halogenation of alkane is an example of
1) electrophilic substitution 2) electrophilic addition
3) nucleophilic substitution 4) free radical substitution
4. The most stable conformation of n-butane is
1) skew boat 2) gauche 3) staggered-anti 4) eclipsed
5. For preparing an alkane, a concentrated solution of sodium or potassium salt of a saturated carboxylic
acid is subjected to
1) hydrolysis 2) oxidation 3) hydrogenation 4) electrolysis
6. Which of the following liberates methane on treatment with water?
1) Silicon carbide 2) Calcium carbide 3) Beryllium carbide 4) Magnesium carbide
7. The reaction/method that does not give an alkane is
1) catalytic hydrogenation of alkenes
2) dehydrohalogenation of an alkyl halide
3) hydrolysis of alkylmagnesium bromide
4) Kolbe’s electrolytic method
8. To prepare a pure sample of n-hexane using sodium metal as one reactant, the other reactant will be
1) ethyl chloride and n-butyl chloride 2) methyl bromide and n-pentyl bromide
3) n-propyl bromide 4) ethyl bromide and n-butyl bromide
9. In Wurtz reaction, if we take CH3Cl and C2H5Cl then product, will be
1) propane + ethane 2) propane 3) propane + ethane + butane 4) propane + butane
10. Which one of the following reactions is expected to readily give a hydrocarbon product in good yields?
1) RCOOK  Electrolytic
oxidation
 2) RCOO Ag   Br2

3) CH3CH3 
Cl2
h
 4)  CH3 3 CCl 
C2H5OH

11. 2-Methylbutane on reacting with bromine in the presence of sunlight gives mainly

23
 1) 1-bromo-3-methylbutane 2) 2-bromo-3-methylbutane
3) 2-bromo-2-methylbutane 4) 1-bromo-2-methylbutane
12. Spatial arrangements of atoms which can be converted into one another by rotation around a C–C
single bond are called
1) Stereoisomers 2) Tautomers 3) Optical isomers 4) Conformers
13. The reagent used for the conversion, CH3CH2COOH  CH3CH2CH3 is
1) LiAlH4 2) soda-lime 3) red P and concentrated HI 4) Zn – Hg/conc. HCl
14. When isobutane is treated with bromine at 127°C, the product formed is
1) a mixture of isobutyl bromide and tert-butyl bromide.
2) a mixture of sec-butyl bromide and tert- butyl bromide.
3) a mixture of isobutyl bromide, sec- butyl bromide and tert- butyl bromide as the major product.
4) almost 100% tert-butyl bromide.
15. Complete combustion of CH4 gives:
1) CO2 + H2O 2) CO2 + H2 3) COCl2 4) CO + CO2 + H2O
16. Which of the following statements are correct?
(i) Decomposition reaction of higher alkanes into smaller fragments by the application of heat is called
pyrolysis.
(ii) Pyrolysis and cracking are different processes.
(iii) Dodecane on pyrolysis gives a mixture of heptane and pentene.
(iv) Pyrolysis follows free radical mechanism.
1) (i), (ii) and (iii) 2) (i), (ii) and (iv) 3) (i), (iii) and (iv) 4) (ii) and (iv)
17. Natural gas is a mixture of:
1) CH4 + C2H6 + C3H8 2) CO + H2 + CH4 3) CO + H2 4) H2O + CO2
18. A petroleum fraction having boiling range 70-200 °C and containing 6-9 carbon atoms per molecule is
called
1) natural gas 2) gas oil 3) gasoline 4) kerosene
19. Which of the following statements are correct?
(i) Stability of conformation is affected due to torsional strain.
(ii) Magnitude of torsional strain depends upon the angle of rotation about C – C bond.
(iii) Eclipsed form has least torsional strain.
(iv) Staggered form has maximum torsional strain.
1) (i) and (iii) 2) (i) and (ii) 3) (iii) and (iv) 4) (i) and (iv)
TOPIC 2: Alkenes
20. Which one of the following heptanols can be dehydrated to hept-3-ene only?
1) Heptan-3-ol 2) Heptan-4-ol 3) Heptan-2-ol 4) Heptan-1-ol
21. Isobutene is the exclusive product of dehydrohalogenation (by a strong base) of
1) isobutyl chloride 2) tert-butyl bromide
3) both 1) and 2) 4) neither 1) nor 2)
22. Compound which gives acetone on ozonolysis:
1) CH3 — CH = CH — CH3 2) (CH3)2C = C (CH3)2 3) C6H5CH = CH2 4) CH3CH = CH2
23. Correct statement about 1, 3 -butadiene is
1) Conjugated double bonds are present 2) Reacts with HBr 3) Forms polymer 4) All of these
24. Allene (C3H4) contains
1) one double bond, one triple bond and one single bond. 2) one triple and two double bonds.
3) two triple and one double bonds. 4) two double and four single bonds.
25. The compound

24
 on reaction with NaIO4 in the presence of KMnO4 gives
1) CH3CHO + CO2 2) CH3COCH3 3) CH3COCH3 + CH3COOH 4) CH3COCH3 + CH3CHO
26. Reaction of HBr with propene in the presence of peroxide gives
1) isopropyl bromide 2) 3-bromo propane
3) allyl bromide 4) n-propyl bromide
27. Acid catalyzed hydration of alkenes except ethene leads to the formation of
1) mixture of secondary and tertiary alcohols 2) mixture of primary and secondary alcohols
3) secondary or tertiary alcohol 4) primary alcohol
28. Alkenes usually show which type of reactions?
1) addition 2) substitution 3) elimination 4) superposition
29. Select the incorrect statement:
1) Bromine is more selective and less reactive.
2) Chlorine is less selective and more reactive.
3) Benzyl free radical is more stable than 2° free radical.
4) Vinyl free radical more stable than alkyl free radical.
30. Conversion of cyclohexene to cyclohexanol can be conveniently achieved by
1) NaOH + H2O 2) Br2—H2O 3) hydroboration, oxidation 4) hydroboration hydrolysis
31.

32. Addition of BH3 followed by H2O2 to trans-2-butene wouldgive a product which is

1) achiral 2) racemic 3) meso 4) optically active
33. Which of the following alcohols cannot be prepared from hydration of an alkene?

34. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene is
1) propene 2) 1-butene 3) 2-butene 4) ethene
35. In the hydroboration - oxidation reaction of propene with diborane, H2O2 and NaOH, the organic
compound formed is:
1) CH3CH2OH 2) CH3CHOHCH3 3) CH3CH2CH2OH 4) (CH3)3COH
36. The test for unsaturation is confirmed by the decolourisation of which of the following
1) Iodine water 2) CuSO4 solution 3) Bromine water 4) All of these
37. In reaction sequence

25
38. Hyperconjugation is more pronounced in
1) 2-methylpropene 2) but-2-ene 3) 2, 3-dimethylbut-2-ene 4) 2-methylbut-2-ene
39. Isopropyl alcohol is obtained by reacting which of the following alkenes with conc. H2SO4 and H2O
1) Ethylene 2) Propylene 3) 2-methyl propene 4) Isoprene
40. In preparation of alkene from alcohol using Al2O3 which is effective factor?
1) Temperature 2) Concentration 3) Surface area of Al2O3 4) Porosity of Al2O3
41. In the presence of peroxide, HCl and HI do not give anti- Markownikoff’s addition of alkenes because
1) one of the steps is endothermic in HCl and HI
2) both HCl and HI are strong acids
3) HCl is oxidizing and the HI is reducing
4) all the steps are exothermic in HCl and HI
42. The nodal plane in the p-bond of ethene is located in
1) the molecular plane
2) a plane parallel to the molecular plane
3) a plane perpendicular to the molecular plane which bisects the carbon - carbon s -bond at right angle
4) a plane perpendicular to the molecular plane which contains the carbon - carbon s -bond.
43. The IUPAC name of the compound having the formula (CH3)3CCH = CH2 is –
1) 3, 3, 3-trimethyl-1-propane 2) 1, 1, 1-trimethyl-1-butene
3) 3, 3-dimethyl-1-butene 4) 1, 1-dimethyl-1, 3-butene
44. The only alcohol that can be prepared by the indirect hydration of alkene is
1) Ethyl alcohol 2) Propyl alcohol 3) Isobutyl alcohol 4) Methyl alcohol
45.

Order of rate of electrophilic addition reaction with HBr will be :

1) IV > I > III > II 2) I > II > III > IV 3) I > III > II > IV 4) IV > I > II > III
46. Which of the following would not rearrange to a more stable form?

TOPIC 3: Alkynes
47. Number of alkynes for formula C5H8 is –
1) 2 2) 3 3) 4 4) 5

26
48. The reagent(s) for the following conversion,

1) alcoholic KOH
2) alcoholic KOH followed by NaNH2
3) aqueous KOH followed by NaNH2
4) Zn/CH3OH
49.
The reagent is
1) Na 2) HCl in H2O 3) KOH in C2H5OH 4) Zn in alcohol.
50. A compound is treated with NaNH2 to give sodium salt. Identify the compound
1) C2H2 2) C6H6 3) C2H6 4) C2H4
51. Which of these will not react with acetylene?
1) NaOH 2) Ammonical AgNO3 3) Na 4) HCl.
52. Which of the following is used for the conversion of 2-hexyne into trans-2-hexene?
1) H2/Pd/BaSO4 2) H2, PtO2 3) NaBH4 4) Liq.NH3/C2H5OH
53. In the reaction

the product formed is

1) propene 2) propyne 3) propyne and propene 4) 4-methylpentyne-2
54. Ammonical silver nitrate forms a white precipitate easily with
1) CH3C  CH 2) CH3C  CCH3 3) CH3CH = CH2 4) CH2 = CH2
55. When acetylene passed through dil. H2SO4 in presence of HgSO4, the compound formed is
1) ether 2) acetaldehyde 3) acetic acid 4) ketone
56. Identify the reagent from the following list which can easily distinguish between 1-butyne and 2-butyne
1) bromine, CCl4 2) H2, Lindlar catalyst 3) dilute H2SO4, HgSO4 4) ammonical Cu2Cl2 solution
57. But–2–yne on chlorination gives
1) 1 –chlorobutane 2) 1, 2 –dichlorobutane
3) 1, 1, 2, 2 –tetrachlorobutane 4) 2, 2, 3, 3 –tetrachlorobutane
58. Combustion of which of the following compound (in the presence of excess of oxygen) does not result
in the change in hybrid state of C atom
1) CH4 2) CH2 = CH2 3) CH3 – CH3 4) HC  CH
59. Which of the following polymer can be used as electrodes in batteries?
1) Polypropene 2) Polyacetylene 3) Polyethene 4) Polyisoprene
60. Which of the following has the lowest dipole moment?

61.

27
62. The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an
alkyne. The bromoalkane and alkyne respectively are

63. Which alkyne will give 3-ethylhexane on catalytic hydrogenation?

64. Reduction of 2-butyne with sodium in liquid ammonia gives predominantly

1) cis - 2 - butene 2) n-butane
3) trans - 2 - butene 4) no reaction
65. Acetylene reacts with HCN in the presence of Ba(CN)2 to yield
1) 1, 1 -dicyanoethane 2) 1, 2-dicyanoethane
3) vinyl cyanide 4) None of these
66. Which of the following will have least hindered rotation around carbon - carbon bond?
1) Ethane 2) Ethylene 3) Acetylene 4) Hexachloroethane
67. Which one of the following compounds will react with methylmagnesium iodide?
1) CH3CH2CH2CH2CH3 2) CH3CH = CH – CH = CH2
3) CH3C  CCH2CH3 4) CH3CH2CH2C  CH
68. Butyne-2 contains:
1) sp hybridised carbon atoms only 2) sp3 hybridised carbon atoms only
3) both sp and sp2 hybridised carbon atoms 4) both sp and sp3 hybridised carbon atoms
69. Acetylenic hydrogens are acidic because
1) Sigma electron density of C – H bond in acetylene is nearer to carbon, which has 50% s-character
2) Acetylene has only one hydrogen on each carbon
3) Acetylene contains least number of hydrogens among the possible hydrocarbons having two carbons
4) Acetylene belongs to the class of alkynes with molecular formula, CnH2n – 2.
TOPIC 4 : Aromatic Hydrocarbons
70. The product of the reaction between ethyl benzene and N-bromosuccinamide is

71. n-Butylbenzene on oxidation will give

1) benzoic acid 2) butanoic acid 3) benzyl alcohol 4) benzaldehyde
72. Aromatic compounds burn with sooty flame because

28
 1) they have a ring structure of carbon atoms
2) they have a relatively high percentage of hydrogen
3) they have a relatively high percentage of carbon 4) they resist reaction with oxygen of air
73. Using anhydrous AlCl3 as catalyst, which one of the following reactions produces ethylbenzene (PhEt)?
1) H3C - CH2OH + C6H6 2) CH3 - CH = CH2 + C6H6
3) H2C = CH2 + C6H6 4) H3C - CH3 + C6H6
74. The conditions for aromaticity is:
1) molecule must have cyclic clouds of delocalised p electrons
2) molecule must contain (4n + 2) p electrons
3) Both 1) and 2) 4) None of the above
75. Benzene is highly unsaturated but it does not undergo addition reaction because
1) p-electrons of benzene are delocalised.
2) cyclic structures do not show addition reaction
3) benzene is a non-reactive compound 4) All of the above
76. Which of the following statements are correct?
(i) Polynuclear hydrocarbons contain two or more benzene rings fused together.
(ii) Polynuclear hydrocarbons have carcinogenic property.
(iii) Polynuclear hydrocarbons are formed on incomplete combustion of organic materials like tobacco,
coal and petroleum.
(iv) They are also produced in human body due to various biochemical reactions.
1) (i), (ii) and (iv) 2) (i), (iii) and (iv)
3) (ii), (iii) and (iv) 4) (i), (ii) and (iii)
77. The most reactive among the following towards sulphonation is
1) toluene 2) chlorobenzene 3) nitrobenzene 4) m-Xylene
78. Bromination of ethyl benzene in presence of light gives

79. During monoalkylation of benzene with CH3Cl in presence of anhydrous AlCl3, an excess of C6H6
must be used because this will
1) increase the chance for collision between CH3+ and C6H6
2) decrease collision between CH3+ and C6H5CH3
3) both 1) and 2) 4) decrease the chance for collision between CH3+ and C6H6.
80. Which of the following is an antiaromatic compound?

29
 NEET PREVIOUS YEARS QUESTIONS
1. Hydrocarbon (A) reacts with bromine by substitution to form an alkyl bromide which by Wurtz reaction
is converted to gaseous hydrocarbon containing less than four carbon atoms. (A) is [2018]
1) CH  CH 2) CH 2  CH 2 3) CH4 4) CH 3  CH 3
2. Which one is the correct order of acidity? [2017]

3. With respect to the conformers of ethane, which of the following statements is true? [2017]
1) Bond angle changes but bond length remains same
2) Both bond angle and bond length change
3) Both bond angles and bond length remains same
4) Bond angle remains same but bond length changes
4. In the reaction H  C  CH
1 NaNH2 / liq.NH3 X 1 NaNH2 / liq.NH3 Y X and Y are [2016]
 2 CH3CH2Br  2 CH3CH2Br
1) X = 1-Butyne ; Y = 3-Hexyne 2) X = 2-Butyne ; Y = 3-Hexyne
3) X = 2-Butyne ; Y = 2-Hexyne 4) X = 1-Butyne ; Y = 2-Hexyne
5. The correct statement regarding the comparison of staggered and eclipsed conformation of ethane, is
[2016]
1) The staggered conformation of ethane is less stable than eclipsed conformation, because staggered
conformation has torsional strain
2) The eclipsed conformation of ethane is more stable than staggered conformation, because eclipsed
conformation has no torsional strain
3) The eclipsed conformation of ethane is more stable than staggered conformation even though the
eclipsed conformation has torsional strain
4) The staggered conformation of ethane is more stable than eclipsed conformation, because staggered
conformation has no torsional strain.
6. In the reaction with HCl, an alkene reacts in accordance with the Markovnikov's rule, to give a product -
chloro-1-methylcyclohexane. The possible alkene is: [2015]

7. 2,3-Dimethyl-2-butene can be prepared by heating which of the following compounds with a strong acid?
[2015]
 CH3 2 CH  CH  CH  CH 2
1) |
2)  CH3 3 C  CH  CH2
CH 3
3)  CH3 2 C  CH  CH2  CH3 4)  CH3 2 CH  CH2  CH  CH2
8. The oxidation of benzene by V2O5 in presence of air produces: [2015]
1) Benzoic anhydride 2) Maleic anhydride 3) Benzoic acid 4) Benzaldehyde
9. The reaction of C6H5CH = CHCH3 with HBr produces: [2015]

30
10. The total number of  -bond electrons in the following structure is :- [2015]

1)8 2)12 3)16 4)4

11. Given:

The enthalpy of the hydrogenation of these compounds will be in the order as :- [2015]
1) III > II > I 2) II > III > I 3) II > I > III 4) I > II > III
12. A single compound of the structure: [2015]

is obtainable from ozonolysis of which of the following cyclic compounds?

13. Which of the following organic compounds has same hybridization as its combustion product (CO2)?
[2014]
1) Ethane 2) Ethyne 3) Ethene 4) Ethanol
14. The most suitable reagent for the following conversion is :- [2019]
2+ +
(1) Na/liquid NH3 (2) H2, Pd/C, quinolone (3) Zn/HCl (4) Hg /H , H2O

31
15. An alkene "A" on reaction with O3 and Zn–H2O gives propanone and ethanal in equimolar ratio. Addition
of HCl to alkene "A" gives "B" as the major product. The structure of product "B" is :- [2019]

(1) (2) (3) (4)

16. Which of the following compound is most reactive in electrophilic aromatic substitution? [2020-COVID]

(1) (2) (3) (4)

17. Which of the following is a free radical substitution reaction? [2020-COVID]

(1) Benzene with Br2/AlCl3 (2) Acetylene with HBr
(3) Methane with Br2/hv (4) Propene with HBr/(C6H5COO)2
18. Dihedral angle of least stable conformer of ethane is : [NEET-2021]
1. 1800 2. 600 3. 00 4. 1200
NaOH , ?
19. CH3CH2COO Na  Heat
CH3CH3  Na2CO3 . [NEET-2021]

Consider the above reaction and identify the missing reagent/chemical.

1) Red Phosphorus 2) CaO 3) DIBAL-H 4) B2 H 6

20. Compound X on reaction with O3 followed by Zn/ H2O gives formaldehyde and 2- methyl
propanal as products. The compound X is: [NEET-2022]

1)3-Methylbut-1-ene 2) 2-Methylbut-1-ene
3) 2-Methylbut-2-ene 4) pent-2-ene

32
 NCERT LINE BY LINE QUESTIONS – ANSWERS
(1.) a (2.) d (3.) d (4.) d (5.) c
(6.) a (7.) a (8.) b (9.) b (10.) a
(11.) d (12.) d (13.) d (14.) b (15.) d
(16.) d (17.) b (18.) b (19.) d (20.) a
(21.) a (22.) a (23.) c (24.) c (25.) c
(26.) b (27.) a (28.) a (29.) d (30.) c
(31.) d (32.) c (33.) d (34.) c (35.) a
(36.) a (37.) c (38.) d (39.) d (40.) a
(41.) c (42.) a (43.) b (44.) b (45.) d
(46.) a (47.) c (48.) b (49.) b (50.) b

TOPIC WISE PRACTICE QUESTIONS - ANSWERS

1) 3 2) 3 3) 4 4) 3 5) 4 6) 3 7) 2 8) 3 9) 3 10) 1
11) 3 12) 4 13) 3 14) 4 15) 1 16) 3 17) 1 18) 3 19) 2 20) 2
21) 3 22) 2 23) 4 24) 4 25) 3 26) 4 27) 3 28) 1 29) 4 30) 3
31) 3 32) 2 33) 4 34) 3 35) 3 36) 3 37) 3 38) 3 39) 2 40) 1
41) 1 42) 1 43) 3 44) 1 45) 4 46) 3 47) 2 48) 2 49) 3 50) 1
51) 1 52) 4 53) 3 54) 1 55) 2 56) 4 57) 4 58) 4 59) 2 60) 2
61) 1 62) 4 63) 4 64) 3 65) 3 66) 1 67) 4 68) 4 69) 1 70) 4
71) 1 72) 3 73) 3 74) 3 75) 1 76) 4 77) 4 78) 3 79) 3 80) 4

NEET PREVIOUS YEARS QUESTIONS-ANSWERS

1) 3 2) 1 3) 3 4) 1 5) 4 6) 3 7) 2 8) 2 9) 4 10) 1
11) 1 12) 4 13) 2 14) 2 15) 3 16) 4 17) 3 18) 3 19) 2 20) 1

NCERT LINE BY LINE QUESTIONS – SOLUTIONS

(1.) (a) Alkynes react with strong base like NaNH 2 ro form sodium acerylide derivative known as
acetylides

(2.) (d) both methyl group cancel each other so net zero dipole moment exists.
(3.) (d) The molecules which do not satisfy Huckel’s Rule or  4n  2 π ‐ electrons rule are said to be
non‐aromatic. The compound (D) has total 4πe . It does not follow (4n  2) rule. So, it is non‐
aromatic compound. Acl other compounds (A, B, C) are planar and have 6πe so, they are
aromatic.
(4.) (d) Both II and IV contains 4nπe and hence, anti‐ aromatic.
(5.) (c) Configurational Isomers

33
(6.) (a) Acidic strength  Electronegativity of carbon  0% of s‐character. So correct order of acidic
CH  CH  CH3  C  CH  CH 2  CH 2  CH 3  CH 3
strength    Ethyne proton can be released more
2 3
sp sp sp
easily than ethene and ethane due to  I effect of CH3 group.

(7.) (a)
(8.) (b) Correct explanation Due to    I effect of alkyl group, electron density increases in alkyl
benzene relative to benzene and hence further substitution occurs to form a polyalkyl‐substituted
benzene.
(9.) (b)
(10.) (a) Cyclopemadienyl cation is a planar cyclic system of 4π ‐ electrons and hence is not aromatic
but it is anti‐aromatic.

(11.) (d) Friedel‐Craft’s reaction. Chlorobenzene,

bromobenzene and chloroethene are not suitable halide component as the C‐X bond acquires
some double bond character due to resonance of lone pair of electrons with π bonds.
CH
(12.) (d) n 2n 2
CH  CH 
Lindlar
CH2  CH2
(13.) (d) Catalyft
Lindlar Catalyst prevents further reduction of ethene to ethane
(14.) (b) Both OCH 3 and CH3 are o, p‐directing groups. The possible positions of attack which are

facilitated both by OCH 3 and CH3 groups are shown. since,

CH 3O group is bulkier than CH3 so, due to steric hindrance, the reaction does not occur at
positions 2 and 6 but instead occurs at position 4.

(15.) (d)
(16.) (d) (A)  T (Hydration) (B)  R (Hydrogenation) (C)  P (Halogenation) (D)  Q
(Polymerisation)
sp sp
CH3  C  C
(17.) (b) Thus, pair of electrons is present in sp‐hybridised orbital.
CH3CH 2CH 2Br  C6H5CO2 O2
(18.) (b) CH3CH  CH2  HBr 
Anti Mark . Add Rule.
 CHCH2CH 2Br

34
(19.) (d)

C6 H6 
CH3Cl/AlC13
 C6 H5CH3 
KMnO4
C6 H5COOH
(20.) (a) Benzoic Acid Friedel Craft alkylation oxide

Benzene Touluene Benzoic Acid

(21.) (a)
Li/NH3
(22.) (a)

(23.) (c) CH3CH2CH2OH  HBr

elimination
H2C  C  CH2

CH 3CH 2 CH 2 Br 
elimination
 CH 3CH 2  CH 2

(24.) (c) Or

(25.) (c) If large amount of KHSO4 is added concentration of NO 2 will decrease and hence the rate of
nitration will be slower. or Mechanism of nitration is HNO3  2H 2 SO4  NO2  2HSO4  H3O If
a large amount of KHSO4 is added then conc. of HSO 4 ions increases and the reaction will be
shifted in a backward direction and rate of nitration will be slower.

(26.) (b) Benzene.

(27.) (a)

35
 1
(28.) (a) enthalpy of hydrogenation  Stability of alkene I  II  III Enthalpy of
stabilityof Alkene
hydrogenation: III  II  I.
1
(29.) (d) Addition HC  CH  3H 2  Ni
 CH 3  CH 3 Substitution CH  CH  Na  CH  C  Na   H 2
2
Polymerisation 3CH  CH 
hot Cu tube
Polymerisation
C6H6
(30.) (c)
(31.) (d) Stability depends on hyperconiugation which further depends on αH.
(32.) (c) Pyrolysis and cracking are the same process.
(33.) (d) Benzene can be obtained by all the compounds given.

(34.) (c) 12 and 3π

(35.) (a)
(36.) (a) Due to restricted rotation about double bond, 2‐butene shows geometrical isomerism.

(37.) (c) CH3 group is o, p‐ directing. of crowding, no substitution occurs at the carbon atom between
the two CH3 groups in m‐ xylene, even though two CH3 groups activate that position.

(38.) (d)
(39.) (d) OCH 3 group is a stronger electron donating group than CH3 group so, C6H5OCH3 has the
fastest rate of reaction with Br2 / FeBr3.
(40.) (a) Structure (A) has a cyclic planar system of 2π electrons so, aromatic
(41.) (c)
(42.) (a) 1‐Butyne reacts with NaNH 2 to give sodium salt while 2‐butyne does not react only terminal
1
CH3  CH2  C  C  H 
NaNH 2
 H3CCHC  CNa  H 2
alkynes are acidic 2
1 Butyne
H3C  C  C  CH 3  No Reaction Terminal alkyne (1‐butyne) reacts with NaNH 2 to form
NaNH 2

sodium acetylide and evolves hydrogen but 2‐butyne not.

(43.) (b) In presence of peroxides, only the addition of HBr to unsymmetrical alkenes does not occur
according to Markovnikov’s rule. Since, alkene (b) is unsymmetrical while alkene (d) is
symmetrical. So, correct option (b).
(44.) (b) During catalytic hydrogenation, the hydrogens are transferred from the catalyst to the same
side of the double bond. Evidently, smaller the number of R substituents, lesser is the steric

36
 hindrance and hence faster is the rate of hydrogenation. So, option (b) with two R groups on the
same side of the molecule is correct.
(45.) (d)
(46.) (a) Iodination is a reversible process so C6 H6  I2 C6H5I  HI, HI formed is oxidised by HNO3
to I 2 otherwise HI will reduce C6 H 5I back to C6H6 .

(47.) (c)

(48.) (b)
(49.) (b) 2 4  2
C H CH  CH2 
decolourise KMnO4 solution but does not give PPt. with AgNO3 solution.
(50.) (b) Alkenes are unsaturated hydrocarbons having double bond so, it gives addition reaction.
TOPIC WISE PRACTICE QUESTIONS - SOLUTIONS
1. (3) Other three methods can be used for the preparation of alkane having at least two carbon atoms.
2. (3)
3. (4)
4. (3) Order of stability : staggered anti > gauche > skew boat > eclipsed.
5. (4)
6. (3)
7. (2) Dehydrohalogenation of an alkyl halide gives an alkene
8. (3)
9. 3)

10. (1) Electrolysis of a concentrated aqueous solution of either sodium or potassium salts of saturated
monocarboxylic acids yields higher alkane at anode.

11. 3)

37
 Ease of replacement of H-atom 3° > 2° > 1°.
12. 4) Spatial arrangements of atoms which can be converted around a C – C single bond are called
conformations or conformers or rotamers.
13. 3)
14. 4) Bromine is less reactive than chlorine and hence more selective, leading to the formation of the
product corresponding to 3° free radical, i.e. tert-butyl bromide.
15. 1) Complete combustion of all organic compounds leads to formation of CO2 + H2O.
16. 3) Pyrolysis and cracking are same process.
17. 1) Natural gas is a mixture of CH4, C2H6 and C3H8.
18. 3)
19. 2) Eclipsed form has maximum torsional strain, while staggered form has the least.
20. 2) Heptan-4-ol has similar alkyl group on both ends of the carbon atom bearing –OH group, hence
dehydration of alcohol will form only one alkene, not a mixture of two alkenes

21. 3)

22. 2)
23. 4) CH2  CH  CH  CH2
1, 3-Butadiene
24. 4)Allene is H 2C  C  CH 2
25. 3)
26. 4)
27. 3)

Addition follows Markownikoff’s rule.

28. 1) Alkenes are unsaturated hydrocarbon having double bond so generally gives addition reactions.
29. 4)

30. 3) Hydroboration – oxidation reaction.

31. 3)

32. 2) Hydroboration - oxidation reaction is a syn-addition.

38
33. (4) Corresponding alkene is not possible.
34. (3) The given molecular formula suggests that the aldehyde formed will be acetaldehyde hence the
alkene will be

35. 3)
36. (3) By adding bromine water to a solution, if the colour of bromine water decolourises then the
compound is unsaturated. This is a confirmatory test for unsaturation.

37. 3)
38. 3)
39. 2)

40. 1)

41. (1)
42. (1) The p bond is formed by the sideways overlapping of two p-orbitals of the two carbon atoms.
The molecular plane does not have any p electron density as the p-orbitals are perpendicular to the plane
containing the ethene molecule. The nodal plane in the p-bond of ethene is located in the molecular
plane.
43. (3)
44. 1)

Except ethyl alcohol, no other primary alcohol can be prepared by this method as the addition of H2SO4
follows Markownikoff’s rule. Generally secondary and tertiary alcohols are obtained.
45. (4) Rate of electrophilic addition  Nucleophilicity of alkene μ stability of carbocation, so order IV > I
> II > III.
46. (3)

is stable carbocation due to presence of s-resonance so it will not rearrange.

47. (2) Three alkynes are possible for the formula C5H8.

39
48. 2)
49. 3) On heating ethylene chloride (1, 1-dichloroethane) with alcoholic potash followed by sodamide
alkyne is obtained

50. 1)
51. 1) Acetylene reacts with the other three as:

52. 4)
53. 3)

54. (1) Terminal alkynes give a white precipitate easily on reaction with ammonical silver nitrate solution.

55. 2)

56. (4) In 1-butyne terminal hydrogen is acidic where as in 2-butyne there is no terminal hydrogen. Thus 2-
butyne will not react with ammonical Cu2Cl2. While 1-butyne, being terminal alkyne, will give red ppt.
with ammonical cuprous chloride
57. (4)
58. (4)
59. (2) Thin film of polyacetylene can be used as electrodes in batteries. These films are good conductors,
lighter and cheaper than the metal conductors.
60. (2) CH3C  CCH3 , being symmetrical, has the lowest dipole moment
61. (1)
62. (4)
63. (4) All alkyne on catalytic hydrogenation give 3-ethylhexane.
64. (3)

40
65. 3)

66. (1) Ethylene has restricted rotation, acetylene has no rotation, hexachloroethane has more rotation than
ethylene but less than ethane because of greater size of the substituent (chlorine) in hexachloroethane
than in ethane (substituent is hydrogen).
67. (4)
68. (4)
69. (1) The acidity of acetylene or 1–alkyne can be explained on the basis of molecular orbital concept
according to which formation of C—H bond in acetylene involves sp-hybridised carbon atom. Now
since s electrons are closer to the nucleus than p electrons, the electrons present in a bond having more s
character will be correspondingly more closer to the nucleus. Thus owing to high s character of the C—
H bond in alkynes (s = 50%), the electrons constituting this bond are more strongly held by the carbon
nucleus i.e., the acetylenic carbon atom or the sp orbital acts as more electronegative species than the
sp2 and sp3 with the result the hydrogen present on such a carbon atom (ºC—H) can be easily removed
as a proton.
70. 4)
71. 1)
72. 3)
73. 3) C6 H 6  CH 2  CH 2 AlCl3
 C6 H 5CH 2CH 3
74. 3)
75. (1)  -Electrons of benzene rings are delocalised throughout the molecule. This makes the molecule
very stable. The stability resists breaking of double bonds for addition.
76. (4) Polynuclear hydrocarbons are not produced in human body by any biochemical reaction. However,
when they enter into human body they undergo various biochemical reactions which finally damage
DNA and cause cancer.
77. (4)
78. (3) Bromination in presence of light leads to side chain substitution. For nuclear substitution we require
halogen carrier.
79. (3)
80. (4)
NEET PREVIOUS YEARS QUESTIONS-EXPLANATIONS
3) CH4   CH3  Br   CH3  CH3
Br2 Na
1. hv ether
 less than four 'C'
Only one central metal atom/ion is present and it follows EAN rule, so it is mononuclear.
2. 1) Correct order is

3. (3) There is no change in bond angles and bond lengths in the conformations of ethane.
4. 1)

5. 4) In stggered conformation any two hydrogen atoms on adjacent carbon atoms are as far apart as
possible thereby minimising repulsion between the electron clouds of  -bonds of two non-bonded H-
atomic (torsional strain)

41
6. 3)

7. 2)

8. 2)

42
9. 4)

10. (1) No. of double bonds = 4

No. of  bond electrons = 2 × no. of double bond = 2 × 4 = 8
11. 1) Enthalpy of hydrogenation
1

stability of alkene
 III > II > I
12. 4)

13. 2) The combustion reaction of ethylene is

14. 2)

15. 3)

16. 4)

+ R effect of -OH group enhances the reactivity inaromatic electrophilic substitution reaction.

43
17. 3)

18. 3)Dihedral angle of least stable conformer of ethane at 00

19. 2) CH3CH2COO Na  NaOH
CaO / 
CH3CH3  Na2CO3
NaOH  CaO  Sodalime .
20. 3-Methylbut-1-ene l

44