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Haloalkanes and Haloarenes

1. Write SN2 mechanism for the conversion of methyl chloride to methyl

alcohol.

The nucleophile attacks from the rare side forming an unstable intermediate which
stabilizes by releasing the leaving agent.

In SN2 mechanism always 100% inverted product is formed.

-][CH3Cl]

∴ Order = 1 + 1 = 2

2. Explain the mechanism of SN1 reaction taking 2-bromo-2-methyl propane

(t-butyl bromide) as an example.
The mechanism involves the following two steps.
Step-1: Formation of carbocation.
t-butyl bromide undergoes ionization to form a t-butyl carbocation.

Step-2: Attack of nucleophile on the carbocation.

The nucleophile OH-can attack the carbocation either from side or back side
to form t-butyl alcohol. This step is fast.

∴ [t-butyl bromide]1 [OH-]0

∴ Order = 1
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3. Aryl halides are extremely less reactive towards nucleophilic substitution

reactions. Give any two reasons.
(i) C-X bond acquires double bond character due to resonance.
(ii) Difference of hybridisation of carbon atom in C-X bond: In Haloarene the C-
atom attached to halogen is sp2 hybridised i.e. greater s character is more
electronegative and can hold the electron pair of C-X more tightly.
(iii)Instability of phenyl cation.
(iv) Because of possible repulsion due to electron rich arene.
(v) Energy of activation for displacement of halogen atom is more. (Any two)

4. Explain Zaitsave rule with an example.

In dehydrohalogenation reaction the major product is that alkene which has the
greater number of alkyl groups attached to the doubly bonded carbon atom.

For example 2-bromopentane gives pent-2-ene as major product.

5. Explain Fittig reaction with general equation.

Two molecules of aryl halides are coupled in presence of sodium metal in dry ether
to give biphenyl. This reaction is called Fittig reaction.

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6. Explain Swarts reaction with an example.

Fluoro alkanes are prepared by heating alkyl chlorides or bromides with salts such
as AgF, Hg2F2 or SbF3 . This reaction is called Swart’s reaction.
CH3Br + AgF CH3F + AgBr.

7. Explain Finkelstein reaction with an example.

Alkyl iodides are often prepared by the reaction of alkyl chlorides/bromides with
NaI in dry acetone. This reaction is known as Finkelstein reaction.

8. Complete the reaction. CH3CH2Br + alc.AgCN …………………

CH3CH2Br + alc.AgCN CH3CH2NC + AgBr

9. Explain Wurtz-Fittig reaction

The coupling of an aryl halide with an alkyl halide in the presence of sodium metal
in dry ether gives alkylarene. This reaction is called Wurtz-Fittig reaction.

10. What is a Racemic mixture?

A mixture containing two enantiomers in equal proportions will have zero optical
rotation, as the rotation due to one isomer will be cancelled by the rotation due to
the other isomer. Such a mixture is known as racemic mixture.

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11. What are enantiomers?

The optically active isomers that are non-superimposable mirror images are called
enantiomers.

12. What is chirality?

The property of a molecule to have nonsuperimposable mirror images.

13. What is asymmetric carbon?

Carbon atom which is bonded to four different atoms or groups.

14. Explain Sandmeyer’s reaction.

Sandmeyer’s reaction is a chemical reaction which is used to synthesize aryl
halides from aryl diazonium salts.

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15. Complete the reaction

16. What is the name of the following reaction?

Wurtz Fittig reaction.

17. What are Grignard reagents? Write its general formula.

Grignard reagents are alkyl magnesium halides, an important class of
organometallic compounds.
General formula: RMgX

18.Explain Wurtz reaction.

Alkyl halide undergo a coupling reaction in the presence of dry ether to form
higher alkanes.

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19.How do you convert chlorobenzene to phenol?

Chloro benzene reacts with sodium hydroxide at 623K temperature and 300
atmosphere pressure to form phenoxide ion which undergoes acid hydrolysis to
form phenol.

20. What is the reagent used to convert alkyl halide into alkene?
Alcoholic KOH

21.How do you get fluoro methane from chloro or bromo methane and name the
reaction?
Chloro or bromo methane when treated with Silver fluoride undergo a halogen
exchange reaction to yield fluoro alkanes.
CH3Br + AgF CH3F + AgBr.
This reaction is called Swartz reaction.

22.Explain Friedel-Crafts acylation with equation by taking chlorobenzene as

example.
When chlorobenzene is treated with acetyl chloride in presence of anhydrous aluminium
chloride, 4-chloroacetophenone is formed as the major product and 2-chloroacetophenone
as the minor product.

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