VELAMMAL NEWGEN SCHOOL SURAPET

GRADE XI CHEMISTRY
HYDROCARBONS- ALKYNES AND ARENES QUESTION BANK
1.In the following question two or more options may be correct.
Which of the following compounds contain all the carbon atoms in the same hybridisation
state?
(a) H—C≡C—C≡C—H (b) CH3—C≡C—CH3 (c) CH2≡C≡CH2 (d) CH2≡CH—CH≡CH2

Ans : (a) and (d).

2.Consider the nitration of benzene using conc. H2SO4 and conc. HNO3. If large amount of
KHSO4 is added to mixture, the rate of nitration will be
(a) unchanged (b) doubled (c) faster (d) slower
Ans : (d) slower. ∵ Less NO2+ will be formed. HNO3 + H2SO4 ⇌ NO2+ + HSO4– + H2O
Presence of K+HSO4– will shift the equilibrium backwards.

3.
(a) X is 2-butyne Y is 2 hexyne (b) X is 1-butyne, Y is 2-hexyne
(c) X is 1-butyne Y is 3-hexyne (d) X is 2-butyne, Y is 3-hexyne
Ans : (c) X is 1-butyne Y is 3-hexyne
HC≡C—CH2—CH3 + NaNH2 NaC≡C—CH2CH3 + CH3—CH2—Br→
CH3—CH2—C≡C—CH2—CH3
4.Predict the correct intermediate, and product in the following reaction

Ans :
 5.Phenyl magnesium bromide reacts with methanol to give
(a) Benzene (b) Toluene (c) Phenol (d) Anisole

Ans :
6.Which compound would give 5-keto 2-methyl hexanal upon ozonolysis followed by reaction
with Zn/H2O?

Ans :
7.For an electrophilic substitution reaction, the presence of a halogen atom in the benzene ring
_______.(a) deactivates the ring by inductive effect (b) deactivates the ring by resonance
(c) increases the charge density at ortho and para position relative to meta position by
resonance
(d) directs the incoming electrophile to meta position by increasing the charge density
relative to ortho and para position.
Ans : (a) and (c). –I but +R effect ∴ ortho and para directing.
8.Four structures are given in options (a) to (d). Examine them and select the aromatic structures.

Ans : (a) and (c).∵ they follow huckel rule, (4n + 2)π electrons which are delocalised.
9.In which of the following, all atoms are coplanar?

Ans : ∵ all ‘C’ are sp2 hybridised, all lie in one plane
10.The compound formed as a result of oxidation of propyl benzene by hot alkaline KMnO4 is
(a) Benzoic acid (b) 2-phenyl ethanoic acid (c) 3-phenyl ethanoic acid
(d) acetophenone
 11.How many number of σ and π-bonds in
Ans : There are 7 σ-bonds and 5 π-bonds.
12.Which type of isomerism is present in CH3CH2OH and CH3OCH3?
Ans : Functional isomerism
13.Which type of isomerism is exhibited by but-1-yne and but-2-yne?
Ans : Positional isomerism is shown by but-1-yne and but-2-yne.
14.Why is addition reaction of bromine to benzene difficult?
Ans : Addition reaction of bromine to benzene is difficult due to delocalisation of π-electrons. It
does not have pure double bonds.
15.What happens when benzene is treated with excess of Cl2 in presence of sunlight? Give
chemical reaction.

Ans :
16.Convert ethyne to propyne.

Ans :
17.Convert but-2-yne to trans-but-2-ene.

Ans :
18.How will you distinguish between but-1-yne and but-2-yne?
Add ammonical cuprous chloride. But-1-yne gives brick red ppt., whereas but-2-yne does not react.
19.Which is more acidic: ethene or ethyne? Why?
Ethyne is more acidic than ethene because it has ‘sp’ hybridised ‘C’ which is more electronegative.
20.What is the trade name of benzene hexachloride?
Ans : Gammaxane
21.Write the structures of products (A and B) of the following reactions:

Ans :

22.Identify ‘A’ and ‘B’ in the following:

Ans :
 23.Write short notes (Give one example):(i) Friedel–Crafts acylation(ii) Markovnikov rule
(i) Friedel–Crafts acylation. When arenes react with acyl halides or acid anhydride in the presence of
AlCl3 as a catalyst to form aromatic ketone, it is called Friedel–Crafts reaction.

(ii) Markovnikov rule. When a polar compound is added to unsymmetrical alkene or alkyne, negative
part goes to that carbon atom which possesses lesser number of hydrogen atoms.

24.(i) Indicate the number of σ and π bonds in HCONHCH3.

(ii) Out of benzene, m-dinitrobenzene and toluene, which will undergo nitration most easily and
why?

Ans :

(ii) The order of ease of nitration is

Nitration is an electrophilic substitution reaction. Since —CH3 group is electron donating group, it
increases the electron density on the benzene ring, thereby facilitating electrophilic substitution
reaction. Nitro group
on the other hand is electron withdrawing group, therefore, it is deactivating, i.e. decreases the
reactivity towards electrophilic substitution reaction.
25.Write IUPAC name of the following compounds:
Ans :

26.Write chemical equations for combustion reaction of the following hydrocarbons:

(i) Butane (ii) Pentene(iii) Hexyne (iv) Toluene
Ans :

27.Why is benzene extra ordinarily stable though it contains three double bonds?
Ans : It is resonance stabilized, that is why it is less reactive inspite of three double bonds. 6π
electrons are delocalised.
28.Explain why the following systems are not aromatic.

Ans :
 29.How will you convert benzene into(i) p-nitrobromobenzene? (ii) m-nitrochlorobenzene?
(iii) p-nitrotoluene? (iv) acetophenone?
Ans :

30.Addition of HBr to propene yields 2-bromopropane, while in the presence of benzoyl peroxide,
the same reaction yields 1-bromopropane. Explain and give mechanism.
Ans :
 31.Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour. Also, give
reason for this behaviour.
Ethyne > Benzene > n-Hexane

In ethyne, ‘C’ is sp hybridised which is most electronegative, attracts shared pair of electrons
towards itself and releases H+ easily.
In benzene, each, ‘C’ is sp2 hybridised, less electronegative, and releases H+ less easily.
In hexane, each ‘C’ is sp3 hybridised, least electronegative, does not release H+ easily, therefore,
least acidic.
32.How would you convert the following compounds into benzene?(i) Ethyne (ii) Ethene(iii) Hexane

33.Write down the products of ozonolysis of 1, 2-dimethylbenzene (o-xylene). How does the
result support Kekule structure for benzene?
Ans :

35.What are the necessary conditions for any compound to show aromaticity?
Ans : (i) Compound should have (4n + 2)π electrons
(ii) π-Electrons should be delocalized.
36.Why does benzene undergo electrophilic substitution reaction easily and nucleophilic
substitutions with difficulty?
Ans : It is because benzene has 6 π-electrons, therefore, electrophile can attack easily.
Nucleophile cannot attack because
it will be repelled by π-electrons.
37.Out of benzene, m-dinitrobenzene and toluene, which will undergo nitration most easily and
why?
Ans : Toluene will undergo nitration most easily because —CH3 group is electron releasing
group. It increases electron density on benzene ring.
38.Suggest the name of a Lewis acid other than anhydrous aluminium chloride which can be used
during ethylation of benzene.
Ans : BF3 can be used.
39.Arrange the following set of compounds in order of their decreasing relative reactivity with an
electrophile, E+ (i) Chlorobenzene, 2, 4-dinitrochlorobenzene, p-nitrochlorobenzene
(ii) Toluene, p-H3C–C6H4–NO2 and p-O2N–C6H4–NO2.

Ans :
40.How will you convert: (i) Propyne into propanone? (ii) Secondary butyl bromide into but-2-ene?

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

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

Ans :

more
stable and gives isopropyl benzene as product.

43.How will you convert benzene into(i) p-nitrobromobenzene? (ii) m-nitrobromobenzene?

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

Ans :

45.Despite their – I effect, halogens are o-and pdirecting in haloarenes. Explain.

Ans : It is because of –I (Inductive effect) but +R effect. Resonance effect is dominating over
inductive effect. That is why halogens are o and p-directing towards electrophillic substitution
reactions.
46.(i) Give reasons: (a) Alkynes are acidic in nature (Give chemical equation to support answer).

(ii) What happens when 2-bromobutane is being treated with KOH (alcoholic)?
Ans : (i) (a) In alkynes, ‘C’ is sp hybridised, which is most electronegative and attracts the shared
pair of electrons and hence release H+ ion easily.

47.(i) Write a chemical equation for Friedel–Crafts reaction.

(ii) Identify A, B, C and D in the following reactions:

48.(i) Write down geometrical isomer of CHCl==CHCl.
(ii) Draw the eclipsed and staggered form of butane in Newman’s projection.
(iii) Complete the following reaction:

Ans :

49.(i) Arrange the following alkenes in increasing order of stability along with reasons.
50.Explain the following: (i) Friedel–Crafts acylation (ii) Wurtz–Fittig reaction
(iii) Kolbe’s electrolytic method (iv) β-Elimination reaction

51.The ring systems having following characteristics are aromatic.

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

Ans : ‘A’ is aromatic as it is planar, sp2 hybridised and 6 π-electrons are delocalised.
‘B’ is not aromatic as 6 π-electrons are not delocalised.
‘C’ is aromatic as 6 π-electrons (4π + 2 unshared electrons) are delocalised.
‘D’ is not aromatic because it has 4 π-electrons which are delocalised.
‘E’ is aromatic because 6 π-electrons are delocalised.
‘F’ has 2 π-electrons which are delocalised therefore it is aromatic.
‘G’ has 8 π-electrons which are not delocalised. So, is not aromatic.
52.Which of the following compounds are aromatic according to Huckel’s rule?

Ans : ‘A’ is not aromatic. It has 8 π-electrons which are not delocalised therefore it is not aromatic.
‘B’ is aromatic because 6 π-electrons are delocalised.
‘C’ is not aromatic because 6 π-electrons are not delocalised.
‘D’ is aromatic because 10π-electrons are delocalised.
‘E’ is aromatic because out of 8 π-electrons, 6 π-electrons are delocalised.
‘F’ has 14 π-electrons which are delocalised and ring is planar.
 53.(i) How can you convert the following: (a) Acetylene to nitrobenzene?
(b) 2-Bromopropane to 1-bromopropane?
(ii) Give a chemical test to distinguish between ethene and ethane.
(iii) Give a brief account for the following statements :
(a) n-Pentane has greater boiling point that isopentane.
(b) CH4 cannot be synthesized by Wurtz reaction.
Ans : (i) (a) Acetylene on cyclic polymerisation will give benzene. Benzene on nitration with conc.
HNO3 and conc. H2SO4 will give nitrobenzene.

(b) 2-Bromopropane will give propene on heating with alc. KOH which will react with HBr in presence
of peroxide to give 1-bromopropane.

(ii) Ethene decolourises Br2 water but ethane does not.

Due to addition reaction taking place, the orange colour of Br2 disappears.

(iii) (a) n-Pentane has higher surface area than isopentane. Hence, the magnitude of van der Waals’
force is higher in n-pentane. Therefore, it has higher boiling point.
(b) Wurtz reaction occurs between two alkyl halides to yield alkane. Methane has only one carbon
atom, hence cannot be prepared by using Wurtz reaction.
54.(i) An alkyl halide (X) of formula C6H13Cl on treatment with alcoholic KOH or
potassiumtert-butoxide give two isomeric alkenes Y and Z (C6H12). Both alkenes on
hydrogenation give 2, 3- dimethylbutane. Predict the structure of X, Y and Z.
(ii) Give the main products of the reactions:
 55.(i) How can you convert: (a) Acetylene to Toluene? (b) But-2-ene to Ethanal?
(ii) Give a chemical test to distinguish between ethane and ethyne.
(iii) Give a brief account for the following statements:
(a) trans pent-2-ene is polar while trans but-2-ene is non-polar.
(b) n-Pentane has greater boiling point than neo-pentane.
(i) (a) Acetylene to Toluene. Acetylene, on heating in presence of Fe tube gives benzene which on
reaction with CH3Cl in presence of AlCl3 gives toluene.

(b) But-2-ene to Ethanal: But-2-ene, on ozonolysis followed by reduction with Zn with and H2O gives
ethanal.

(ii) On reaction of ethane with bromine, the brown colour of bromine does not get decolourised, but
due
to addition reaction in unsaturated compound ethyne, reddish brown colour of bromine is
decolourised.
(iii) (a) In trans pent-2-ene, the polarity is unequal in opposite directions but in trans but-2-ene, the
dipole moment is equal in opposite directions and hence cancel leading to non-polar molecule.

(b) Due to branching, the surface area of neo-pentane, is lesser than n-pentane. Hence, the
magnitude of van der Waals’ force of attraction in n-pentane is greater and it has higher boiling point.

56.
(ii) An alkene ‘A’ contains three C–C, eight C–H σ bonds and one C–C π bond. ‘A’ on ozonolysis
gives two moles of an aldehyde of molar mass 44. Write the IUPAC name of ‘A’.
(iii) Addition of HBr to propene in presence of benzoyl peroxide yields bromopropane. Explain with
suitable mechanism steps.
Ans :

Due to the presence of sp3 hybridised carbon atom, the system is not
planar. Also, the system is not fully conjugated.
(ii) An aldehyde with molar mass 44 amu is CH3CHO (ethanal).
 57.(i) Identify ‘A’, ‘B’, ‘C’ and ‘D’

(ii) Out of benzene and toluene, which will undergo nitration easily, and why?

(ii) Toluene undergoes nitration easily because —CH3 group is electron releasing group, it increases
electron density on benzene ring.
58.(i) Convert:(a) Benzene to p-nitrobromobenzene (b) Ethyl chloride to ethene
(ii) Give mechanism of addition of HBr to propene.
(iii) Write a note on Friedel–Crafts alkylation.
(i) (a) Benzene reacts with Br2 in presence of FeBr3 to give bromobenzene which on nitration with
conc. HNO3 and conc. H2SO4 give p-nitrobromobenzene.

(b) Ethyl chloride on treatement with alc KOH gives ethene.

(ii) Mechanism of addition of HBr to propene:

(iii) Friedel–Craft’s alkylation: It is the reaction of benzene with alkyl halide in presence of anhydrous
aluminium chloride. The reaction results in the formation of alkyl benzene.

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 59.(i)Out of benzene, m-dinitrobenzene and toluene,which will undergo nitration most easily & why?
(ii) Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour.
Also, give reason for this behaviour.
(iii) Explain with example:(a) Wurtz reaction (b) Acidic dehydration(iv) Convert propyne to
propanone.
(i) Nitration is an electrophilic substitution reaction involving the attack of NO2+ (nitronium ion), an
electrophile. Electron withdrawing group as —NO2 group decreases the electron density on benzene
ring and electron donating group as —CH3 group increases the electron density on benzene ring,
facilitating the attack of an electrophile in the ring. Hence toluene will undergo nitration most easily. It
will stabilize the intermediate carbocation formed.

Since s-orbitals are closer to the nucleus, hence due to more s-character in ethyne (sp hybridised),
the hybridised orbital is nearest to this carbon atom in comparison to sp3 or sp2 hybridised carbon.
This leads to the movement of C—H bond pair more towards sp hybridised carbon, leading to the
development of partial positive charge on the hydrogen attached to sp hybridised carbon. Thus, such
a hydrogen behaves as acidic hydrogen. Hence order of acidic nature is, Ethyne > Benzene >
n-Hexane.
(iii) (a) Wurtz Reaction: Alkyl halides on treatment with sodium metal in dry ether medium give higher
alkanes.This is called Wurtz reaction and is used for the preparation of alkanes with even number of

carbon atoms.
(b) Acidic Dehydration: Alcohols on heating with conc. H2SO4 form alkenes with elimination of one
water molecule. Since a water molecule is lost in the presence of acid, the reaction is called acidic
dehydration of alcohols.

(iv) Propyne on reaction with H2O in presence of dil H2SO4 and HgSO4 gives propanone.

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60.(i) Give a chemical test to distinguish between CH3—CH2—C≡≡CH and CH3—C≡≡C—CH3
(ii) An alkene C4H6 upon ozonolysis gives 2 moles of formaldehyde and 1 mole of glyoxal. What
is the name of alkene?
(iii) Explain:(a) Why does Benzene not undergo addition reaction? (b) Explain Wurtz’s reaction.

(iii) (a) It is due to delocalization of π-electrons

(b) Wurtz’s Reaction:When 2 moles of alkyl halide react with Na metal in presence of dry ether as
a solvent, higher alkane is formed.