Explain why 2-bromopropane reacts with sodium iodide in acetone over 104 times faster than bromocyclopropane. hint: examine the transition state for each of the reactions.

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The reaction of 2-bromopropane reacts with sodium iodide in acetone is an example of Sn2 reaction.

The I - attacks from backside to give the transition state for both.

If we compare the transition state for cyclobromopropane 2-bromopropane then we see in case of cyclobromopropane transition state, one of the H is very close to the incoming I -.

This results in steric strain and less stability of the transition state. Hence 2-bromopropane reacts with sodium iodide in acetone over 104 times faster than bromocyclopropane.

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