What Is the Expected Product From Benzyl Fluoride and Et2AlCN Reaction?

[rmjmu507]

Homework Statement

What would be the expected product from the reaction of benzyl fluoride with Et2AlCN if the reaction is (a) 1st order w.r.t. aluminum (b) 2nd order w.r.t. aluminum?

2. The attempt at a solution

Would you form benzyl cyanide and diethyl aluminum fluoride? That's the only thing I can think of...I learned that this reagent is useful for adding CN across a a,b-unsaturated compound, but benzyl fluoride is not unsaturated (except for the phenyl ring, but I highly doubt reaction would occur there).

Does this seem logical? Could someone explain to me the effects that reaction order would have on the products formed?

 

[nate808]

I would first clarify the conditions of the reaction. Is it being run under specific conditions or in a specific solvent? This information can greatly affect the expected products.

Under first order conditions, the rate of the reaction would only depend on the concentration of aluminum, and the reaction would follow a pseudo-first order kinetics. In this case, the expected product would be benzyl cyanide and diethyl aluminum fluoride, as you have correctly suggested.

Under second order conditions, the rate of the reaction would depend on the concentration of both aluminum and benzyl fluoride. This would result in a different product distribution, potentially leading to the formation of other byproducts such as benzyl alcohol or benzyl chloride. The exact product distribution would also depend on the reaction conditions and the reactivity of each component.

In general, the reaction order can affect the selectivity and yield of the desired product, as well as the formation of any byproducts. It is important to consider the reaction conditions and the steric and electronic effects of each component to predict the expected products accurately. Further experimentation and analysis would also be necessary to fully understand the effects of reaction order on the products formed.