Help with prediction products of a reaction!
4-phenylbutanoyl chloride + AlCl3 --> ?
the molecular formula of the product is C10H10O, and I need to determine the product. I was thinking an acylium ion would form, and then the carbonyl carbon would form a bond with the ring to make a bicyclic compound. Is this correct? I am also not sure where it would bond on the ring (ortho/meta/para).
Thanks!
I'm not sure, but I do not think that a reaction would occur. ALCl3 usually acts as a catalyst, and would just form an ionic bond with the oxygen on the carbonyl of the compound; there isn't another reactant to form some other compound.
To predict the products of a reaction, it is essential to analyze the reactants and their characteristics. In this case, we have the reactant 4-phenylbutanoyl chloride (C10H11ClO) reacting with AlCl3. The molecular formula you provided for the product, C10H10O, indicates a loss of one chlorine atom and a rearrangement of the atoms to give a compound with fewer degrees of unsaturation.
Based on your understanding, the reaction can proceed by the acylium ion formation. The AlCl3 acts as a Lewis acid, which will accept the chloride ion from the 4-phenylbutanoyl chloride, creating an acylium ion intermediate. However, instead of a bicyclic compound forming by bonding with the ring, it is more likely that a rearrangement will take place.
To determine the position of the acylium group on the phenyl ring (ortho/meta/para), we need to consider the directing effect of the substituents present on the phenyl ring. Since the acylium group is electron-withdrawing, it will have a meta-directing effect.
Therefore, the predicted product can be a rearranged compound where the acylium group is attached to the meta position (position 3) of the phenyl ring. The final product would be 4-phenyl-3-butanone (C10H10O).
Remember that the prediction of reaction products is not always straightforward, and it is based on a variety of factors, including reactant reactivity, reaction conditions, and the stability of the resulting compounds. It's always a good idea to consult reliable sources or experimental data to confirm your predictions.