Solution

SURE SHOT 2M, HALO ALKANES AND ARENES

Class 12 - Chemistry

1.

C H3 C H3 C H3

| KOH(alc),Δ | HBr,P eroxide |

2. i. C H 3 − C − C H3 −−−−−−−−−−−−−→ C H3 − C = C H2 −−−−−−−−−−−−→ C H3 − C H − C H2 Br
| Dehydroha log enation Isobutyl bromide
Anti Mark. Addition
Br

tert−Butylbromide

ii.

P eroxide

3. C H 3 C H2 C H = C H2 + HBr−−−−−−−−−−−−−−−−→C H3 C H3 C H2 C H2 − Br
But−1−ene { Anti - Markownikoff's rule} 1−Bromobutane

1 2 3

4. i. C H 2 = C H C H2 Br
3−bromoprop−1−ene

ii. (CCI3)3CCl The structure can be drawn as

a
bh
Su

tris-( trichloromethyl) chloromethane

G

5.

6. Phenol (C6H5OH) contains the phenyl ring bonded to the hydroxyl group -OH. Due to the resonance stabilization of the Phenol
ring, the hydroxyl group attached to phenol it gains a partial double bond character, which makes it difficult for the cleavage of
this bond in the order to be subject to chlorination.

Resonance structure of phenol.

Conc. H2 S O4 ,443 K HBr

7. C 2 H5 OH −−−−−−−−−−−→ C H2 = C H2 −−→
′ ′
A

KOH(aq)

C H3 C H2 Br −−−−−→ C H3 C H2 OH
′ ′ ′ ′
B C

I2 /N aOH

−−−−−−→ C H3 I
′ ′
D

yellow ppt
′
W illiamso n s

8. C6 H5 ON a + C2 H5 C l −−−−−−−→ C6 H5 − O − C2 H5 + N aC l
Sodium phenoxide synthesis P henetole

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 9. A mixture of NaBr and H2SO4 gives Br2 gas as a product. Molecule (b) will not react with Br2 gas because of the stable molecule
that is formed due to resonance stabilization.
10. By treating benzene with Br2 in dark in presence of Fe, it gets converted to bromobenzene which on treatment with Na in dry
ether gets converted to biphenyl.

11. Step 1: Treat methyl bromide with aq. KCN to give methane nitrile (increasing the number of C by 1)
Step 2: Carry out hydrolysis of methane nitrile to give acetic acid (ethanoic acid)
KCN H2 O

C H3 Br −−−→ C H3 C N −−→ C H3 C OOH

methyl bromide Acetic acid

12. There are two compounds that can yield 1-chloro-1-methylcyclohexane are methylenecyclohexane and 1-methylcyclohex-1-ene.
The reaction involves as follows:

a
bh
Su

13. In an aqueous solution, KOH almost completely ionizes to give OH - ions. OH - ion is a strong nucleophile, which leads the alkyl
chloride to undergo a substitution reaction to form alcohol.
R − C l + K OH(aq) → R − OH + K C l
Alcohol
G

Alkyl

chloride

On the other hand, an alcoholic solution of KOH contains alkoxide (RO )ion, which is a strong base. Thus, it can abstract a
−

hydrogen from the β carbon of the alkyl chloride and form an alkene by eliminating a molecule of HCl.
R − C H2 − C H2 − C l + K OH(alc) → R − C H = C H2 + K C l + H2 O
β α
Alkene

Alkyl chloride

OH
−
ion is a much weaker base than RO ion. Also, OH −
ion is highly solvated in an aqueous solution and as a result, the
−

basic character of OH ion decreases. Therefore, it cannot abstract a hydrogen from the β -carbon.
−

14. The other resonance structures are as follows:

The functional group present in the above molecules is ortho-para directing instead of meta-directing as electron density is more at
ortho and para positions.
CH3

′ |
Markowniko v s addition

15. C H 3 CH = C (C H3 )
2
+ HBr−−−−−−−−−−−−−−→ C H3 − C H2 − C − C H3
|
2−Methylbut−2−ene

Br

2 - Bromo - 2 - methylbutane

16. i. Wurtz reaction : It is used to convert an alkyl halide into alkane by reacting the alkyl halide with sodium in presence of dry
ether.

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 Dry ether

C H3 C l + 2N a + C H3 C l −−−−−→ 2N aC l + C H3 − C H3

ii. Wurtz-Fittig reaction: It is used to convert an aryl halide into corresponding hydrocarbon with the help of sodium in
presence of dry ether.

17. All eight structure isomers of C5H11Br are as follows:

a
bh
Su

18. Secondary alkyl halides prefer to undergo SN1 reaction than primary alkyl halides because of formation of more stable 2°
G

carbocation.
Hence, out of the given pair C H 3
− C H − C H3 would undergo SN1 reaction faster.
|

Br

19. H3-CH2-CH=CH2 +HBr → CH3-CH2-CH(Br)-CH3

This reaction happens according to Markonikoffs rule
Now reacting this with alcoholic KOH gives alkenes
CH3-CH2-CH(Br)-CH3 + KOH (alc) → CH3CH=CHCH3 + KBr + H2O

20. Monobromobenzene (C6H5Br) can be prepared from aniline, C6H5NH2 by Sandmeyer’s reaction. When aniline suspended in cold

mineral acid is treated with sodium nitrite (NaNO2), a diazonium salt(N2+Cl-) is formed. Mixing the diazonium salt with cuprous
bromide(CuBr/HCl) results in the replacement of the diazonium ion by –Br, forming monobromobenzene.

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21. The electrophilic substitution of arenes with iodine is reversible in nature and require the presence of an oxidising agent (HNO3,
HIO4) to oxidise the HI formed during iodination.

22. i. a.

b.

SN1 reaction proceeds via the formation of carbocation. The alkyl halide (a) is 3o while (b) is 2o Therefore, (a) forms 3o

carbocation while (b) forms 2o carbocation. Greater the stability of the carbocation, faster is the rate of SN1 reaction. Since

3o carbocation is more stable than 2o carbocation. (a), i.e. 2-chloro-2-methylpropane, undergoes faster SN1 reaction than
(b) i.e., 3-chloropentane.

ii. a.

a
bh
b.

The alkyl halide (a) is 2o while (b) is 1o.2o carbocation is more stable than 1o carbocation. Therefore, (a), 2-chloroheptane,
Su

undergoes faster SN1 reaction than (b), 1-chlorohexane.

23. Step 1 Treat but-1-ene with HBr, in presence of peroxide to bring about anti-markownikov addition
Step 2 Treat the resulting 1-bromobutane with aq KOH to bring about substitution to give an alcohol
Step 3 Treat the resulting butan-1-ol with SOCl2 in presence of pyridine to give 1-chlorobutane
G

peroxide

C H3 − C H2 − C H = C H2 + HBr −−−−−→ C H3 − C H2 − C H2 − C H2 Br
aq.KOH SOC l2 ,pyridine

−−−−−→ C H3 − C H2 − C H2 − C H2 OH −−−−−−−−−→ C H3 C H2 C H2 C H2 C l
peroxide

24. H3C − C = C H − C H2 − C H3 + HBr −−−−−→ H3 C − C H − C HBr − C H2 − C H3

| |

CH3 CH3

25. Allyl Chloride, CH2=CH—CH2Cl, is more readily hydrolyzed than n-propyl chloride, CH3—CH2—CH2Cl, because of the

presence of the σ bond which gives the property of resonance stabilization to the CH3=CH2—CH2+ carbocation to be very stable.
Due to the formation of the carbocation, the molecule undergoes hydrolysis more readily while no such stabilisation of
carbocation is found in n- propyl chloride.

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