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Chapter 3: Problem 61

A commonly used free-radical initiator is AIBN (azobisiso-butyronitrile). What are the products of its decomposition in an inert solvent?

Short Answer

Expert verified
The products of AIBN decomposition in an inert solvent are dinitrogen (N2) gas and two isobutyronitrile free radicals, which can be represented as: AIBN -> N2 + 2 (·CH2C(CH3)2CN). The inert solvent does not react with the free radicals generated.

Step by step solution

01

Identify the structure of AIBN

AIBN, or azobisisobutyronitrile, has the chemical formula: C8H12N4. Its structure consists of two isobutyronitrile groups connected by an azo group (-N=N-). Each isobutyronitrile group contains a -C(CH3)2-CN segment. The azo group is responsible for its properties as a free-radical initiator.
02

Decomposition of AIBN

When AIBN is heated or exposed to UV light, the azo group (-N=N-) undergoes cleavage or bond dissociation, generating two nitrogen atoms (N2) and two isobutyronitrile free radicals. The process can be represented as the following equation: AIBN -> N2 + 2 (·CH2C(CH3)2CN) In this reaction, the two nitrogen atoms combine to form dinitrogen gas (N2), which is a major byproduct. Meanwhile, the remaining two isobutyronitrile groups become free radicals. Free radicals are highly reactive, as they possess unpaired electrons.
03

Products formed in an inert solvent

Since the decomposition of AIBN takes place in an inert solvent, this means that the solvent will not react with the free radicals generated. Thus, the products of AIBN decomposition in an inert solvent will be dinitrogen (N2) gas and two isobutyronitrile free radicals. These free radicals may further react with other compounds in the reaction system if they are present, like in polymerization reactions. To summarize, the products of AIBN decomposition in an inert solvent are: 1. Dinitrogen (N2) gas 2. Two isobutyronitrile free radicals

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