Date : 18-12-2024 STD 12 Science Chemistry Total Marks : 46

SECTION A () Answer The Following Questions In One Sentence.[1 Marks Each] [8]

1. Give the IUPAC names of the following compound:

CHF2CBrClF

Ans. : CHF2 CBrClF

F Cl

| |

2 1
F− CH − C −F

Br

1-bromo-1-chloro-1, 2, 2-trifluoro ethane.

2. How the following conversion can be carried out?

tert-Butyl bromide to isobutyl bromide.
Ans. : Br

KOH(alc)/Δ HBr/Peroxide

CH3 − C − CH3 −−−−−−−−−−−−−→ CH3 − C = CH2 −−−−−−−−−−−−−−−−→ CH3 − CH − CH2 − Br

(Dehydrohalogenation) (Anti-Markovnikov addition)

| | |

B CH CH
3. Discuss the nature of C–X bond in the haloarenes.

Ans. : In haloarenes, C—X bond acquires a partial double bond character due to
resonance. As a result, the bond cleavage in haloarene is difficult than haloalkane and
therefore, they are less reactive towards nucleophilic substitution reaction.

In haloalkane, the carbon atom attached to halogen is sp3 hybridised while in case of

haloarene, the carbon atom attached to halogen is sp2 -hybridised.

The sp2 hybridised carbon with a greater s-character is more electronegative and can hold

the electron pair of C—X bond more tightly than sp3 hybridised carbon in haloalkane with
less s-character. Thus, C—Cl bond-length in haloalkane is 177 pm while in haloarene is 169
Pm.

4. Name the following halides according to IUPAC system and classify them as
alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
m-ClCH2C6H4CH2C(CH3)3

Ans. : m-ClCH2 C6 H4 CH2 C(CH3 )3

Page 1
1-chloromethyl-3-(2,2-dimethylpropyl) benzene (aryl halide).

5. What do you understand by the term optical activity of compounds?

Ans. : The property of certain compounds to rotate the plane of polarised light in a
characteristic way when it is passed through their solutions is called optical activity of
compounds.

6. Write the structures of the following organic halogen compound.

1,4-Dibromobut-2-ene.

Ans. : 1,4-Dibromobut-2-ene.
Br − CH2 − CH = CH − CH2 − Br

1 2 3 4

7. Give the IUPAC names of the following compound:

ClCH2C≡CCH2Br

Ans. : ClCH2 C≡CCH2 Br

4 3 2 1
Cl − CH2 − C ≡ C − CH2 − Br

1-bromo-4-chloro but-2-yne.

8. Write the IUPAC name of the following compound:

CH3

CH2 = CH − C − OH

CH3

Ans. : 2-Methylbut-3-en-2-ol

SECTION B () Given Section consists of questions of 2 marks each. [38]

9. Match the items of Column I and Column II

Column I Column II
(i) SN1 reaction (a vic-dibromides
)
(ii) Chemicals in fire (b gem-dihalides
extinguisher )
(iii Bromination of alkenes (c Racemisation
) )
Page 2
(iv Alkylidene halides (d Saytzeff rule
) )
(v) Elimination of HX from (e Chlorobromocarb
alkylhalide ) ons

Ans. :
Column I Column II
(i) SN1 reaction (c) Racemisation

(ii) Chemicals in fire extinguisher (e) Chlorobromocarbons

(iii) Bromination of alkenes (a) vic-dibromides

(iv) Alkylidene halides (b) gem-dihalides
(v) Elimination of HX from alkylhalide (d) Saytzeff rule

Explanation:
i. A mixture containing two enantiomers in equal proportions will have
zero optical rotation, such a mixture is known as racemic mixture. The
process of conversion of enantiomer into a racemic mixture is known as
racemisation. If an alkyl halide follows SN1 mechanism then racemisation

takes place while if it follows SN2mechanism than inversion takes places.

ii. Chlorobromocarbons are used in fire extinguishers.
iii. In vicinal dihalides, halogen atoms are present on the adjacent carbon
atom. Bromination of alkanes will give vicinal dihalides.
iv. Alkylidene halides are named gem-dihalides. In gem-dihalides halogen
atoms are present on same carbon atom.
v. Elimination of HX from alkylhalide follows Saytzeff rule. This rule states
that “in dehydrohalogenation reactions, the preferred product is that
alkene which has the greater number of alkyl groups attached to the
doubly bonded carbon atoms”.
10. Write the mechanism of the following reaction:
HBr

CH3 CH2 OH −−→ CH3 CH2 Br + H2 O

Ans. :

Page 3
11. Which of the following compounds (a) and (b) will not react with a mixture of
NaBr and H2SO4. Explain why?
a. CH3 CH2 CH2 OH

b.

Ans. :
b. As mixture of NaBr and H2SO4 gives Br2 gas. ¯
¯¯¯¯¯¯

2NaBr + 3H2 SO4 −→ 2NaHSO4 + SO2 + Br 2 + 2H2 O

Phenol (b) rects with Br2 to form 2, 4, 6-tribromophenol.

But CH 3 CH 2 CH 2 OH (a) does not react with Br2 water.

12. Which compound in each of the following pairs will react faster in SN2
reaction with -OH? Why?
i. CH3Br or CH3I.
ii. (CH3)3CCI or CH3CI.

Ans. :
i. CH3I, Because iodine is a better leaving group due to its larger size. Page 4
ii. CH3Cl, the presence of bulky group on the carbon atom in (CH3)2CCl
has an inhibiting effect.
13. Write structures of main compounds A and B in each of the following
reactions:
+
CH3 MgBr/H O LiAlH 4

i.
3

CH3 CH2 CH −−−−−−−−−−−−→A−−−−−→B

ii.

Ans. :
i. A = CH3CH2CO-CH3, B = CH3CH2-CH(CH3)-OH
ii. A = C6H5CHO, B = C6H5-CH=N-NH2

14. Write the mechanism of the following reaction:

EtOH− H2 O

nBuBr + KCN −−−−−−−→ nBuCN

Ans. : The given reaction is an SN2 reaction. In this reaction, CN - acts as the nucleophile
and attacks the carbon atom to which Br is attached. CN -ion is an ambident nucleophile
and can attack through both C and N. In this case, it attacks through the C-atom.

15. Which one in the following pairs undergoes SN1 substitution reaction faster
and why?

Ans. :
SN1 reaction takes place through the formation of carbocation; greater is the stability of

carbocation faster is the rate of SN1 reaction, stability of carbocation follows the order 3°

> 2° > 1°, thus:-

Page 5
16. Aryl halides are extremely less reactive towards nucleophilic substitution.
Predict and explain the order of reactivity of the following compounds
towards nucleophilic substitution:

Ans. :
After the attachment of the nucleophile at the carbon carrying -Cl, the intermediate
compound is stabilised due to resonance. Due to electron withdrawing nature of-NO2 , the

nucleophile is easily attached to the benzene ring. Greater the number of -NO2 groups in

the molecule, greater will be the ease with which the nucleophile will be attached. Hence,
the order of reactivity is III > II > I.

17. Match the structures of compounds given in Column I with the classes of
compounds given in Column II.
Column I Column II
(i) CH3 − CH − CH3 (a) Aryl halide
|

(ii) CH2 == CH − CH2 − X (b) Alkyl halide

(iii) (c) Vinyl halide

(iv) CH2 == CH − X (d) Allyl halide

Ans. :
Column I Column II

(i) CH3 − CH − CH3 (b) Alkyl halide

|

X
Page 6
(ii) CH2 == CH − CH2 − X (d) Allyl halide
(iii) (a) Aryl halide

(iv) CH2 == CH − X (c) Vinyl halide

Explanation: The conditions for different classes of haloalkanes or haloarenes are

satisfied as mentioned below,
a. Alkyl halides: In alkyl halides, the halogen atom is bonded to an alkyl
group (R)
b. Allyl halides: These are compounds in which halogen atom iis bonded
to an sp3 - hybrdised carbon atom next to carbo-carbon double bond.
(C=C) i.e. to an allylic carbon.
c. Vinyl halides: These are compounds in which the halogen atom is
bonded to an sp2-hybridised carbon atom of carbon-carbon double bond
(C=C).
d. Aryl halides: These are the compounds in which the halogen atom is
bonded to the sp2 hybridised carbon atom of an aromatic ring.

18. Answer the following questions:

Amongst the isomeric dihalobenzenes which isomer has the highest melting
point and why?
Ans. : Amongst the isomeric dihalobenzenes para-isomer has the highest melting point.
This is due to greater symmetry of para-isomer that fits in crystal lattice better as
compared to ortho and meta isomers.

19. How are the following conversions carried out?

i. Benzyl chloride to benzyl alcohol,
ii. Methyl magnesium bromide to 2-methylpropan-2-ol.
Ans. :

Page 7
20. Write one chemical reaction each to illustrate the following:
i. Hofmann’s bromamide reaction.
ii. Gabriel phthalimide synthesis.
Ans. :
i. Hoffmann Bromamide Reaction.
R-CONH 2 +Br2 + 4NaOH → R-NH 2 + Na 2 CO3 + 2NaBr + 2H 2 O.

ii. Gabriel pthalimide synthesis.

21. Identify whether the following pairs of compounds are structural or

geometrical isomers:
i.

ii.

Ans. :
i. Geometrical.
ii. Structural.
22. What are the IUPAC names of the insecticide DDT and benzenehexachloride?
Why is their use banned in India and other countries?
Ans. :
IUPAC name of DDT is 2, 2-bis (4-chlorophenyl)-l, 1, 1-trichloroethane.

IUPAC name of benzenehexachoride is 1, 2, 3, 4, 5, 6-hexachlorocyclohexane.

Their use is banned in India andother countries because they are highly toxic and are not
biodegradable. Instead they are stored in the fatty tissues and their concentration keeps
increasing in the food chain.

23. Write structures of compounds A and B in each of the following reactions:

i.

ii.

Ans. :
i.
ii.

24. How will you bring about the following conversion?

Ethane to bromoethene.

Ans. : Ethane to bromoethene.

Br2 /UV light

HC3 − HC3 −−−−−−−→ CH3 − CH2 Br + HBr

or heat

Ethane Bromoethane

⏐
⏐
− HBr⏐KOH(alc),Δ
⏐
↓
Br2 / CCl 4

BrCH2 − CH2 Br ←−−−−− CH2 ≡ CH2

vic-Dibromide Ethene
⏐
⏐
Δ⏐KOH(alc)
⏐
↓

CH2 = CHBr

Bromoethane

25. Some alkylhalides undergo substitution whereas some undergo elimination

reaction on treatment with bases. Discuss the structural features of alkyl
halides with the help of examples which are responsible for this difference.

Ans. : An alkyl halide with alpha- hydrogen atoms when reacted with a base or a
nucleophile, has two competing routes: substitution (via SN1 or SN2 mechanism) and
elimination. Which route will be taken up depends upon the nature of alkyl halide,
strength, size of base / nucleophile and reaction conditions. Thus, a bulkier nucleophile will
prefer to act as a base and abstracts a proton rather than approach a tetravalent carbon
atom due to steric hinderence and vice-versa.
Commonly a primary alkyl halide will prefer a SN2 reaction, and in case of a secondary
halide-either SN2 or elimination process would occur depending upon the strength of base

/ nucleophile. A tertiary halide with bulkier alkyl group would undergo either 'SN1 or
elimination' based upon the stability of carbocation or the more substituted alkene.
Examples:
Elimination reaction-
KOH(alc)/△

1. CH3 − CH2 − CH2 − Br −−−−−−−−−−−−−→ CH3 − CH = CH2

(Dehydrohalogenation)

1 − Bromopropane Propene

2. If the same reaction is carried out in presence of aq KOH, 1-propanol will

be the product.
aqueous KOH

CH3 − CH2 − CH2 − Br −−−−−−−−→ CH3 − CH2 − CH2 OH

26. Match the reactions given in Column I with the names given in Column II.
Colu
Column I
mn II
Nucle
ophili
c
(
(i arom
a
) atic
)
subst
itutio
n
Electr
ophili
c
(
(i CH − CH == CH2 + HBr −→ CH3 − CH arom
b
3

i) − CH 3
| Br atic
)
subst
itutio
n

Saytz
(i ( eff
ii c elimi
) ) natio
n
Electr
(i ( ophili
v dc
) ) additi
on

Nucle
ophili
( alc.KOH
( c
v CH3 CH2 CHCH3 −−−−−→ CH3 CH
e subst
) itutio
== CHCH3 | Br
)
n
(SN1)

Ans. :
Column I Column II
( Electrophilic
(i) b aromatic
) substitution
CH3 − CH == CH2 + HBr −→ CH3 − CH − CH3 (
(ii Electrophilic
| d
) addition
Br )
(
(ii Saytzeff
e
i) elimination
)

( Nucleophilic
(i
a substitution
v)
) (SN1)

alc.KOH
(
(v CH3 CH2 CHCH3 −−−−−→ CH3 CH == CHCH3
Saytzeff
c
elimination
|
)
Br )
Explanation:
i. In this reaction, an electrophile CF attacks on to the benzene ring and
substitution takes place.
ii. In this reaction, addition of HBr takes place on to the doubly bonded
carbons of propene in accordance with Markownikoff’s rule and
electrophilic addition takes place.
iii. In this reaction, the reactant is secondary halide. Here, halogen atom is
substituted by hydroxyl ion. As it is secondary halide so it follows
SN1 mechanism.
iv. In this reaction, halogen atom is directly bonded to aromatic ring. So, it is
nucleophilic aromatic substitution as OH– group has substituted halogen of
given compound.
v. It is an elimination reaction. It follows Saytzeff elimination rule.

27. Draw the structure of major monohalo product in each of the following
reactions:

Ans. :

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