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a) Most important chemical reactions of haloalkanes are their substitution reactions. 

 i) What is SN1 reaction? 

ii) Arrange the four isomeric bromo butanes in the increasing order of their reactivity towards SN1 reaction.

b) How will you prepare chlorobenzene from benzene diazonium chloride?

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a) i) SN1 reaction is a unimolecular nucleophilic substitution reaction. It involves the substitution of a weaker nucleophile by a stronger one and follows first-order kinetics, i.e., the rate of reaction depends upon the concentration of only one reactant. It occurs in two steps. In step I, the polarised C – X bond undergoes slow cleavage to produce a carbocation.
ii) SN1 reaction follows the order 10 alkyl halides < 2° alkyl halides < 3° alkyl halides.
CH3CH2CH2CH2Br < (CH3)2CHCH2Br < CH3CH2CH(Br)CH3 < (CH3)3CBr

b) By Sandmeyer reaction – When freshly prepared benzene diazonium chloride solution is mixed with cuprous chloride the diazonium group is replaced by -Cl to form chlorobenzene.

OR

By Gatterman reaction – When freshly prepared benzene diazonium chloride solution is treated with hydrochloric acid in presence of copper pow- der the diazonium group is replaced by -Cl to form chlorobenzene.

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