55.2k views
1 vote
Free radical bromination is a slower reaction than chlorination but it is a synthetic route often used to make alkyl bromides. Alkyl fluorides are not made by free radical halogenation. Explain why free radical fluorination is not a viable route for the synthesis for these compounds.

1 Answer

5 votes

Final answer:

Free radical fluorination is highly reactive and unselective, making it an unsuitable method for producing alkyl fluorides, compared to the more controlled free radical bromination and chlorination. Alkyl halides are better synthesized by other less vigorous and more selective methods.

Step-by-step explanation:

Free radical fluorination is not a viable synthetic route for producing alkyl fluorides because of the high reactivity of fluorine. The bond dissociation energy of fluorine is lower than that of chlorine or bromine, making fluorine radicals extremely reactive. This leads to uncontrollable reactions and a lack of selectivity when fluorine reacts with alkanes. In contrast, free radical bromination is more selective due to the relatively slower and more controlled reaction with alkanes.

Alkyl halides are important intermediates in the synthesis of various organic compounds. While chlorination and bromination reactions of alkanes can be controlled by temperature and light to yield desired haloalkanes, fluorination is too vigorous and can lead to complex mixtures of products, which makes it unsuitable for obtaining pure alkyl fluoride compounds.

Instead of free radical reactions, alkyl fluorides are typically prepared through other methods such as the nucleophilic substitution reactions where the leaving group is a better leaving group than fluoride, ensuring the desired alkyl fluoride is the main product.

User Markfickett
by
8.0k points