Draw the Sn1 intermediate and Sn2 transitions state for both ethyl-2-chloroacetate and benzyl bromide (α-bromotoluene). Use...

Draw the Sn1 intermediate and Sn2 transitions state for both ethyl-2-chloroacetate and benzyl bromide (α-bromotoluene). Use these structures to explain the differences in reactivity between these two compounds.

Solutions

Expert Solution

Under SN1 condition, benzyl bromide form benzyl cation which is resonance stabilised. Under SN2 codition the transition state is stabilised due to conjugation of breaking and forming bonds with pi-system of phenyl ring. Thus, benzyl bromide has good reactivity under both the SN1 and SN2 conditions.

Under SN1 condition, ethylbromo acetate is has poor reactivity becasue the carbocation intermediate primary and moreover attached to an electron withdrawing group that make it very unstable. It is very reactive under SN2 condition because Br is attached to a primary carbon and presence of an electron withdrawing group that makes it more electrophilic that favours mucleophilic attack.

queen_honey_blossom answered 10 months ago

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