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Although Ethyl chloride has more alpha hydrogens, cation formed by Benzyl chloride would show resonance and therefore show higher stability and faster rate, shouldn't that be more reactive?
The reactivity of benzyl chloride is primarily influenced by the presence of the benzyl group, which stabilizes the carbocation formed during reactions. Electron-donating groups on the benzene ring can increase reactivity, while electron-withdrawing groups can decrease it. Solvent and temperature also play significant roles in determining the reactivity of benzyl chloride.
Benzyl chloride reacts slowly with water to form benzyl alcohol and hydrochloric acid. This reaction is a hydrolysis, where water breaks the carbon-chlorine bond in benzyl chloride. The rate of this reaction can be affected by factors such as temperature and the pH of the water.
Benzyl chloride is considered less stable because it readily undergoes various reactions due to the presence of the benzyl group adjacent to the chloro atom. This group stabilizes the formation of a carbocation, making it more susceptible to nucleophilic attack compared to other alkyl halides where such stabilization is absent.
In nucleophilic substitution reactions, benzyl chloride typically undergoes an SN1 mechanism. This involves the formation of a benzyl carbocation intermediate when the chlorine atom leaves, followed by the attack of the nucleophile. The stability of the benzyl carbocation is crucial in facilitating this type of reaction mechanism.
Benzyl chloride generally reacts faster than vinyl chloride due to the stability of the carbocation intermediate formed in its reactions. However, it reacts slower than some alkyl chlorides, particularly tertiary alkyl chlorides, where steric hindrance and the stability of the carbocation can significantly accelerate the reaction rate. The specific conditions and the nature of the nucleophile also affect these rates.