Which type of solvents should be avoided when working with alkyl halides?

When working with alkyl halides, it is important to avoid protic solvents. Protic solvents are those that have an -OH group or can donate a hydrogen bond, such as water, alcohols, or carboxylic acids. The concern with protic solvents is that they can lead to unwanted side reactions. Alkyl halides can participate in nucleophilic substitution or elimination reactions, and in the presence of protic solvents, these reactions may favor competing mechanisms, such as hydrolysis or the formation of carbocations, which can negatively impact the desired reaction outcome.

For example, in the case of nucleophilic substitution reactions, a protic solvent can solvate nucleophiles and reduce their reactivity, thereby slowing down the reaction rate or favoring the formation of unwanted products. Additionally, in the case of sensitive alkyl halides, the presence of protic solvents may lead to the cleavage of C-X bonds (where X is a halide) or lead to the formation of more unstable intermediates.

In contrast, non-polar solvents are typically more compatible with alkyl halides and facilitate the nucleophilic reactions by not interfering with the interactions between the alkyl halide and the nucleophile. Aqueous solvents