tributyltin-hydride-bu3snh-can-be-used-to-synthetically-reduce-alkyl-halides-in-

Question

Tributyltin hydride (Bu₃SnH) can be used to synthetically reduce alkyl halides. In this process, a halogen atom is replaced by a hydrogen atom. Suggest a mechanism for the initiation and propagation steps for the reaction below.

Using the following bond-dissociation enthalpies, calculate the values of ΔH for the proposed steps and determine whether each step is energetically favorable.

Accepted Answer

Initiation step:

(1) ΔH = +190 kJ/mol

(2) ΔH = –56 kJ/mol

Propagation step:

(1) ΔH = –243 kJ/mol

(2) ΔH –103 kJ/mol

The overall enthalpy of the reaction is highly exothermic, making this mechanism energetically favorable.

Answer

Initiation step: ΔH = +190 kJ/mol

Propagation step:

(1) ΔH = –119 kJ/mol

(2) ΔH = –103 kJ/mol

The overall enthalpy of the reaction is highly exothermic, making this mechanism energetically favorable.

Answer

Initiation step: ΔH = +190 kJ/mol

Propagation step:

(1) ΔH = +119 kJ/mol

(2) ΔH = +103 kJ/mol

The overall enthalpy of the reaction is highly endothermic, making this mechanism energetically favorable.

Answer

Initiation step:

(1) ΔH = –190 kJ/mol

(2) ΔH = +56 kJ/mol

Propagation step:

(1) ΔH = +243 kJ/mol

(2) ΔH +103 kJ/mol

The overall enthalpy of the reaction is highly endothermic, making this mechanism energetically favorable.

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