How can we determine that which alkyl halide is supposed to undergo elimination-1 reaction and which one will undergo E-2 reaction?

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    $\begingroup$ An E1 elimination takes place in 2 stages with passage through a carbocation: any alkyl structure which promotes the stability of a carbocation will rather go through an E1 elimination. The general rule is that a tertiary alkyl will rather go through an E1 while a primary an E2. The basic principle is to write down the carbocation that would form: if it is stabilized (inducing effect, mesomer) then it is indeed an E1 elimination otherwise it is an E2 $\endgroup$ – Nicolas Feb 15 at 10:14

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