1.

(a). Which of the following two compounds would react faster by S_(N^(2)) pathway, 1-bromobutane or2-bromobutane and why? (b). Allyl chloride is more reactive than n-propyl chloride towards nucleophilic substitution reaction. Explain why?

Answer»

Solution :(a) In `S_(N^(2))` pathway, steric hindrance is involved. The order of reativity of the alkyl halides is `:1^(@) lt 2^(@) lt 3^(@)`

1-Bromobutane being a primary alkyl halide will offer less steric hindrance to the attacking nucleophile and will react faster than 2-bromobutane in `S_(N^(2))` reaction.
(b). ALLYL chloride is more reactive than n-propyl chloride TOWARDS nucleophilic substitution reaction, (`S_(N^(1))` reaction). it readily ionises to GIVE a carbocation which is resonance stabilised.

The other COMPOUND n-propyl chloride `(n-C_(3)H_(7)Cl)` is very little ionides since the n-propyl carbocation is not resonance stabilised. therefore, ionisation leading to `S_(N^(1))` reaction is quicker in allyl chloride than in n-propyl chloride.


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