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Rank in relative order the reactivity of primary, secondary, tertiary, allylic, benzylic and aromatic halides in...

Rank in relative order the reactivity of primary, secondary, tertiary, allylic, benzylic and aromatic halides in silver nitrate/ethanol test. Explain the reason for this difference in reactivity.
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Answer #1

SOLUTION:

Alkyl halides react with AgNO3 to roduce precipitate of AgX as:

RX + AgNO3 --------> AgX + RONO2

The rate at which the precipitate of AgX will be formed depends upon the reactivity of alkyl halide. The above reaction proceeds by SN1 mechanism, hence the alkyl halide which produces more stable cabocation will react faster (or produce ppt faster). On this bases the reactivity order coincides with order of stability of carbocation. Therefore the reactivity of alkyl halides is given below.

Benzylic > allylic = tertiary > secondary > primary > aromatic.

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