We have recently studied mechanisms for nuclephilic substitution at saturated ca

Question

We have recently studied mechanisms for nuclephilic substitution at saturated carbon atom sites. A similar reaction also occurs with some aromatic halides. The reaction shown below gives the product in 96% yield. With unsaturated carbon atoms, there are generally two likely mechanisms for substitution, an associative process similar to that seen in acyl substitution earlier this semester or a dissociative mechanism similar to the similar to the SN1 process we have discussed recently. Two such mechanisms are provided below: Design an experiment that could differentiate between the two mechanisms proposed above. Then create a set of reactions, similar to those provided lo you in the class group activities that supports one of the two proposed mechanisms and is inconsistent with the other Your set should include at least three reactions (including complete reactant and product structuresl that involve the above reaction type with changes in reactant structure and specific results such as differences in relative rates, stereochemistry or regkn chemistry These reactions are to be simulated data and need not reflect the accepted reaction mechanism for this reaction typc.however.as indicate above, your results should support the prediction of one mechanism and contradict that of the other. If you choose relative rates, you need only indicate the reactions in order of fastest to slowest rather than assigning specific rates. Associative Mechanism Dissociative Mechanism Explain how the results of your proposed reactions support one mechanism and contradict the other.

Explanation / Answer

If you observe the given two types of reactions, first one is SN2 and the second one is SN1. That means that, in the slowest step of SN2, both the reactants take part and in the slowest step of SN1, only one reactant takes part in the reaction. So, to know what type of mechanism the rection is undergoing, we can vary the amount of the reactants and observe the effect of the rate of ther reaction. Since, the rate of the reaction is determined the slowest step in the mechanism.

For example, if the reaction is SN1, no matter how much we vary the amount of the amine, the rte of the reaction should not change whereas for SN2, the rate changes as we vary the amounts of the reactants.

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