Whilst Et₃CCl is unreactive towards water even at elevated temperatures, Et₃SiCl is hydrolyzed rapidly. Explain the origin of these differences and provide a reaction scheme with mechanistic details for the hydrolysis of Et₃SiCl.

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Explanation:

In discussing the reason why Et₃SiCl is more easily hydrolysed than Et₃CCl, we must remember that the electronegativity difference between silicon and chlorine is much higher than the electronegativity difference between carbon and chlorine.

As a result of this, the Si-Cl bond in Et₃SiCl is more polar and hence susceptible to attack by water than the C-Cl bond in Et₃CCl.

Also, it is postulated that the presence of vacant d orbitals on silicon assists hydrolysis in Et₃SiCl. Such vacant orbitals are absent in carbon hence Et₃CCl does not undergo hydrolysis.

The reaction scheme is shown in the image attached to this answer.

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