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11th std Chemistry Bestie

With additional question & answers

Name :
Std & Sec :
School :

Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D.

PG Assistant in chemistry
Government Higher Secondary School - Vallipattu
Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
13. HYDROCARBONS
1 Give IUPAC names for the following compounds
1) CH3 – CH = CH – CH = CH – C ≡ C – CH3 : octa – 2, 4 – diene – 6 – yne
2)

: 5 – ethyl – 4, 5 – dimethyl – 2 – hexyne

3) (CH3)3 C – C ≡ C – CH (CH3)3 : 2, 2, 5 – trimethyl – 3 – hexyne

4) ethyl isopropyl acetylene : 2 – methyl – 3 – hexyne
(CH3)2 – CH – C ≡ C – CH2 CH3
5) CH ≡ C – C ≡ C – C ≡ CH : hexa – 1, 3, 5 – triyne
2 Identify the compound A, B, C and D in the following series of reactions

Ans:
alc. KOH Cl2 / CCl4
CH3-CH2-Br → CH2 = CH2 → CH2 – CH2
-HBr
Ethylene Cl Cl
(A) Ethylene dichloride (B)
i) O3 ii) Zn / H2O NaNH2
2 HCHO + H2O2 CH ≡ CH
Formaldehyde (C) Acetylene (D)
3 Write short notes on ortho, para directors in aromatic electrophilic substitution
reactions.
• When mono substituted benzene undergoes an electrophilic substitution reaction, the rate
of the reaction and the site of attack of the incoming electrophile depends on the functional
group already attached to it.
• Some groups increase the reactivity of benzene ring and are known as activating groups.
• Some groups which decrease the reactivity are known as deactivating groups.
• We further divide these groups into two categories depending on the way they influence
the orientation of attack by the incoming groups.
• Those which increases electron density at ‘ortho’ and ‘para’ position are known as ortho-
para directors
• while those which increase electron density at ‘meta’ position is known as meta-directors.
Ortho and para directing groups:
• All the activating groups are ‘ortho-para’ directors.
• Eg: –OH, –NH2, –NHR, –NHCOCH3, –OCH3, –CH3, –C2H5 etc.
• Let us consider the directive influences of phenolic (-OH) group. Phenol is the resonance
hybrid of following structures.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933

• In these resonance structures, the (-) charge residue is present on ortho and para position
of ring structure.
• Therefore, phenolic group activates the benzene ring for electrophilic attack at ‘ortho’ and
‘para positions and hence –OH group is an ortho-para director and activator.
Meta directing groups:
• Generally, all deactivating groups are meta-directors.
• Eg: –NO2, –CN, –CHO, –COR, –COOH, –COOR, –SO3H etc.
• Let us consider the directive influence of aldehyde (-CHO) group. Benzaldehyde is the
resonance hybrid of following structures.

• Here overall density of benzene ring decreases due to –I effect of –CHO group there by
deactivating the benzene for electrophilic attack.
• However resonating structure shows that electron density is more in meta position,
compared to o & p-position. Hence –CHO group is a meta-director and deactivator.
4 How is propyne prepared from an alkylene dihalide?
alcoholic KOH
CH3-CH-CH2 → CH3-C≡CH + 2 KBr + 2 H2O
Δ
Br Br propyne
1, 2 – dibromo propane
5 An alkylhalide with molecular formula C6H13Br on dehydro halogenation gave two
isomeric alkenes X and Y with molecular formula C6H12. On reductive ozonolysis, X and
Y gave four compounds CH3COCH3, CH3CHO, CH3CH2CHO and (CH3)2CHCHO. Find the
alkylhalide.
An alkylhalide with molecular formula C6H13Br
CH3 – CH – CH – CH2CH3
CH3 Br
Δ alcoholic KOH

CH3 – C = CH – CH2 – CH3 CH3 – CH – CH = CH – CH3

CH3 CH3
2 – methyl pent – 2 – ene 2 – methyl pent – 3 – ene
1) O3 1) O3
2) Zn / H2O 2) Zn / H2O

CH3COCH3 + CH3CH2CHO (CH3)2 – CH – CHO + CH3CHO

So, the alkyl halide is 3 – bromo – 2 – methyl propane.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
6 Describe the mechanism of nitration of benzene.

Reagents: Conc.HNO3 / Conc. H2SO4 ; Electrophile: NO2+ (Nitronium ion)

Mechanism:
Step – 1:

Step – 2:

Step – 3:

7 How does Huckel rule help to decide the aromatic character of a compound. (Sep-21,
Jun-23)
A compound may be aromatic, if it obeys the following rules
(i) The molecule must be co-planar
(ii) Complete delocalization of π electron in the ring
(iii) Presence of (4n+2) π electrons in the ring where n is an integer (n=0,1,2….)
This is known as Huckel’s rule.
8 Suggest the route for the preparation of the following from benzene.
1) 3 – chloro nitrobenzene

2) 4 – chlorotoluene

3) Bromo benzene

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
4) m - dinitro benzene

9 Suggest a simple chemical test to distinguish propane and propene.

• Propene decolourises reddish brown colour of bromine water, but propane does not
decolourise bromine water.
• Propene decolourises pink coloured acidified KMnO4 solution but propane does not
decolourise it.
10 Describe the conformers of n - butane. (Jun-19)
n-Butane may be considered as a derivative of ethane, as one hydrogen on each carbon
is replaced by a methyl group
Eclipsed conformation:
In this conformation, the distance between the two-methyl group is minimum. So, there
is maximum repulsion between them and it is the least stable conformer.
Anti or staggered form
In this conformation, the distance between the two methyl groups is maximum and so
there is minimum repulsion between them. And it is the most stable conformer.
The following potential energy diagram shows the relative stabilities of various
conformers of n-butane.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
11 What happens when isobutylene is treated with acidified potassium permanganate?

12 How will you convert ethyl chloride in to

i) ethane
Zn / HCl
CH3CH2Cl → CH3 – CH3 + HCl
2[H]
Ethane
ii) n – butane
dry ether
CH3CH2Cl + ClCH2CH3 + 2Na → CH3CH2CH2CH3
n – butane
13 Explain Markownikoff's rule with suitable example.
“When an unsymmetrical alkene reacts with hydrogen halide, the hydrogen adds to the
carbon that has more number of hydrogen and halogen add to the carbon having fewer
hydrogen”. Eg:

14 Write the chemical equations for combustion of propane.

CH3-CH2-CH3 + 5O2 3CO2 + 4H2O + Energy

15 What happens when ethylene is passed through cold dilute alkaline potassium
permanganate.
Cold dilute alkaline KMnO4
CH2=CH2 + H2O → CH2 – CH2 + MnO2
H2 O+[O]
OH OH
Ethylene glycol
16 Write the structures of folowing alkanes.
1) 2, 3 – Dimethyl – 6 – (2 – methyl propyl) decane

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
2) 5 – (2 – Ethyl butyl) – 3, 3 – dimethyldecane

3) 5 – (1, 2 – Dimethyl propyl) – 2 – methylnonane

17 How will you prepare propane from a sodium salt of fatty acid?
NaOH / CaO
CH3CH2CH2COONa → CH3CH2CH3 + Na2CO3
Δ
Sodium butyrate Propane
18 H + / Heat HBr
CH3 – CH(CH3) – CH(OH) – CH3 → (A) major product → (B) major product.
Identify A and B.

19 Complete the following:

Lindlar Catalyst
i) 2 – butyne →
Lindlar Catalyst
CH3 – C ≡ C – CH3 + H2 →
I2
ii) CH2 = CH2 → ?

Zn / C2 H5 OH
iii) CH2 – CH2 → ?
Br Br
Zn / C2 H5 OH
→

H2 O
iv) CaC2 → ? (Jun-23)

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
20 How will you distinguish 1 – butyne and 2 – butyne?
• 1 – butyne and 2 – butyne can be distinguished by treating it with ammonical silver nitrate.
• 1 – butyne gives white precipitate with ammoniated silver nitrate and gives red precipitate
with ammoniated cuprous chloride, but 2 – butyne does not reacts with ammonical AgNO3
solution.

21 Write a short note on Corey – House mechanism?

An alkyl halide and lithium di alkyl copper are reacted to give higher alkane.
CH3CH2Br + (CH3)2 LiCu CH3CH2CH3 + CH3Cu + LiBr
22 What are hydrocarbons present in LPG? Give its uses.
A mixture of propane and butane present in LPG. It is used as fuel for household
cooking purpose.
23 Define polymerisation? (Jun-19)
A polymer is a large molecule formed by the combination of larger number of small
molecules. The process in known as polymerisation.
Red hot iron tube
Eg: nCH2 = CH2 → ( CH2 – CH2 )n
873K

24 How does polystyrene prepared from styrene? Give its uses.

free radical polymerisation
nCH2 = CH → ( CH2 – CH2 )n
Uses: it is used to prepare disposable plates, mugs, insulators in refrigerators, freezers, etc
25 What is BHC? How is it prepared (May-22)? Give its uses. (or) how benzene is converted
into BHC? (May-24)
Benzene reacts with three molecules of Cl2 in the presence of sun light or UV light to
yield Benzene Hexa Chloride (BHC) C6H6Cl6. This is known as gammaxane or Lindane.
Uses: it is a powerful insecticide.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
26 How does acetylene react with ozone? (Jul-19)

27 Give the uses of acetylene?

• Acetylene is used in oxy acetylene torch used for welding and cutting metals.
• It is used for manufacture of PVC, polyvinyl acetate, polyvinyl ether, orlon and neoprene
rubbers.
28 What happens when acetylene is passed through red hot iron tube? (Mar-19, Sep-21) (or)
How does benzene prepared from the following? (Mar-24)
a) Acetylene: (Mar-19, Mar-24)
Ethyne undergoes cyclic polymerization on passing through red hot iron tube. Three
molecules of ethyne polymerises to benzene.

b) Phenol: (Mar-19, Mar-24)

C6H5OH + Zn C6H6 + ZnO
Phenol
29 Define Friedel Craft’s Alkylation? (or) How does toluene prepared from benzene? (Mar-
19, Mar-23)

30 Define Friedel Craft’s Acylation (Acetylation)? (Mar-23)

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
31 Define Birch reduction? (Jul-22)

32 Explain Anti-Markovnikoff ’s Rule (or) Peroxide Effect (or) Kharasch Addition?

The addition of HBr to an alkene in the presence of organic peroxide, gives the anti
Markovnikoff’s product. This effect is called peroxide effect.

peroxide
CH3 – CH = CH2 + HBr → CH3 – CH2 – CH2 – Br
(C6 H5 CO)2 O2

Mechanism:
The reaction proceeds via free radical mechanism.
Step:1

Step:2

Step:3
The Bromine radical adds to the double bond in the way to form more stable alkyl free
radical.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
Step:4

33 Explain the structure of benzene?

1. Elemental Analysis and molecular weight determination have proved that the molecular
formula of benzene is C6H6. This indicates that benzene is a highly unsaturated
compound.
2. Benzene could be constructed as a straight chain or ring compound but it not feasible
since it does not show the properties of alkenes or alkynes.
3. Benzene reacts with bromine in the presence of AlCl3 to form mono bromo benzene. It
indicates that all the six hydrogen atoms in benzene were identical. This is possible only if
it has a cyclic structure of six carbons each containing one hydrogen.
4. Benzene can add on to three moles of hydrogen in the presence of nickel catalyst to give
cyclohexane. This confirms cyclic structure of benzene and the presence of three carbon-
carbon double bond.
5. In 1865, August Kekule suggested that benzene consists of a cyclic planar structure of six
carbon with alternate single and double bonds. There were two objections:
(i) Benzene forms only one ortho disubstituted products whereas the Kekule’s structure
predicts two o-di substituted products as shown below.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
(ii) Kekule’s structure failed to explain why benzene with three double bonds did not give
addition reactions like other alkenes.
6. The phenomenon in which two or more structures can be written for a substance which
has identical position of atoms is called resonance. The actual structure of the molecule is
said to be resonance hybrid of various possible alternative structures. In benzene,
Kekule’s structures I & II represented the resonance structure, and structure III is the
resonance hybrid of structure I &II

7. Spectroscopic measurements show that benzene is planar and all of its carbon-carbon
bonds are of equal length 1.40A°. This value lies between carbon-carbon single bond
length 1.54A° and carbon-carbon double bond length 1.34A°.
8. All the six carbon atoms of benzene are sp2 hybridized. six sp2 hybrid orbitals of carbon
linearly overlap with six 1s orbitals of hydrogen atoms to form six C - H sigma bonds.
Overlap between the remaining sp2 hybrid orbitals of carbon forms six C-C sigma bonds.
9. All the σ bonds in benzene lie in one plane with bond angle 120°. Each carbon atom in
benzene possesses an unhybridized p-orbital containing one electron. The lateral overlap
of their p-orbital produces 3 π- bond The six electrons of the p-orbitals cover all the six
carbon atoms and are said to be delocalised. Due to delocalization, strong π-bond is
formed which makes the molecule stable.
10. Hence unlike alkenes and alkynes benzene undergoes substitution reactions rather
addition reactions under normal conditions.

11. Hence, there are three ways in which benzene can be represented.

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 Dr.R.Karthic M.Sc., B.Ed., M.A(Edu)., M.Phil., Ph.D. P.G Assistant, GHSS – vallipattu, 9943119933
34 Explain the conformations of ethane?
The two tetrahedral methyl groups can rotate about the carbon – carbon bond axis
yielding several arrangements called conformers. The extreme conformations are staggered
and eclipsed conformation. There can be number of other arrangements between staggered
and eclipsed forms and their arrangements are known as skew forms.
Eclipsed conformation:
• In this conformation, the hydrogen’s of one carbon are directly
behind those of the other.
• The repulsion between the atoms is maximum and it is the least
stable conformer.
Staggered conformation:
• In this conformation, the hydrogens of both the carbon atoms are
far apart from each other.
• The repulsion between the atoms is minimum and it is the most
stable conformer.
Skew Conformation:
The infinite numbers of possible intermediate conformations
between the two extreme conformations are referred as skew conformations.
35 Write Sabatier- Sendersens reaction?
Ni
CH2 = CH2 + H2 → CH3 - CH3
298 K
36 Write wurtz reaction?
dry ether
CH3 – Br + 2Na + Br – CH3 → CH3 - CH3 + 2NaBr
37 Write Wurtz – Fittig Reaction?
ether
C6H5Br + 2Na +CH3I → C6H5CH3 + NaBr + NaI
38 Write Friedel Craft’s Reaction?
anhydrous AlCl3
C6H6 + CH3Cl → C6H5CH3 + HCl

Don’t wait for the opportunity, create one – Dr. A.P.J. Abdul Kalam

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