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. Write a mechanism for the cleavage of butyl isopropyl ether with HI at 100°C to form exclusively isopropyl alcohol and 1-iodobutane. Explain why butyl alcohol and isopropyl iodide are not formed in the reaction.

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ElennaF

Answer:

Explanation:

In this reaction, the ether is cleaved by SN2 , as I⁻ is a strong nucleophile

So we have the following steps

  • SN2
  1. Protonation of oxygen in ether, improving the ability of both sides to be a leaving group as alchohols
  2. I⁻ performs nucleophilic attack on 1st carbon of butyl side, releasing Isopropanol as leaving group and leaving Iodobutane behind

Now, even though butanol can become a leaving group in this reaction, this is unfavourable, as isopropyl group has large steric hindrance which prevents nucleophilic attack on isopropyl side of the ether.

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