5.In the addition of HCI to cyclohexene in acetic acid, the ratio of cyclohexylacetate to cyclohexyl chloride drops significantly when tetramethylammoniumchloride is added in increasing concentrations. These effects are not observedwhen the same reaction conditions are used with styrene. Explain why thisdifference in product distribution is observed (using structures and words).HCICIacetic acidcyclohexenestyrenecyclohexyl acetateHCIacetic acid+cycloehexyl chlorideCH3H3C-N-CH3CH3Tetramethylammoniumchloride

The phase transfer catalysts are the compounds that facilitate the transfer of the reactants and the reagents from one phase to another during a multi-phase reaction. These catalysts increase the rate of the reaction by facilitating the movement of the reactants to the required phase to carry out the reaction, thereby decreasing the chances of formation of any by-products. In the absence of phase transfer catalyst TMACl (tetra methyl ammonium chloride), the cyclohexene reacts with HCl in the presence of acetic acid as,The reaction proceeds via electrophilic addition mechanism. Here, acetic acid acts as both a solvent and a nucleophile leading to the formation of equivalent amounts of chlorocyclohexane and cyclohexyl acetate. In presence of TMACl as a catalyst the reaction proceeds as,TMACl acts as a phase transfer catalyst which causes the transfer of chloride ions from aqueous phase to organic phase, and the reaction takes place there. This causes a decrease in the concentration of acetyl ions, decreasing the formation of cyclohexyl acetate. The presence of TMACl causes the chloride ion to exclusively attack on the cyclohexyl cation, making chlorocyclohexane as the major product. The reaction of styrene with HCl follows a different mechanism. The reaction follows electrophilic aromatic substitution, where the benzyl cation formed is stabilized by resonance due to the aromatic ring. The carbocation is then attacked by chloride ion, which forms the desired product. The reaction is not sensitive to the concentration of nucleophile in the organic phase, hence the presence of TMACl does not have any effect on the concentration and the type of product formed. The differences in the products on the addition of TMACl to cyclohexene and styrene have been shown above.