1
Question
Out of CH3−CH−CH2−Cl|CH3 and CH3−CH2−CH−Cl|CH3, which is more reactive towards SN1 reaction and why?
which is more reactive towards SN1 reaction and why?
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Solution
Since the first step of the SN1 reaction is loss of a leaving group to give a carbocation, the reactivity will be proportional to the stability of the carbocation. Carbocation stability increases with increasing substitution of the carbon (tertiary > secondary > primary).
CH3−CH(CH3)−CH2Cl (1-chloro-2-methyl propane) forms carbocation CH3−CH(CH3)−CH+2
CH3−CH2−CH(CH3)−Cl (2-chlorobutane ) forms carbocation CH3−CH2−(CH3)CH+
which is more stable and thus the compound 2−chlorobutane is more reactive than 1−chloro−2−methylpropane isomer.
CH3−CH(CH3)−CH2Cl (1-chloro-2-methyl propane) forms carbocation CH3−CH(CH3)−CH+2
CH3−CH2−CH(CH3)−Cl (2-chlorobutane ) forms carbocation CH3−CH2−(CH3)CH+
which is more stable and thus the compound 2−chlorobutane is more reactive than 1−chloro−2−methylpropane isomer.
which is more stable and thus the compound 2−chlorobutane is more reactive than 1−chloro−2−methylpropane isomer.
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