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Chapter 13: Problem 276

Draw a reaction coordinate diagram for the solvolysis of \(2,2,2\) -triphenylethyl chloride in acetic acid. Pay special attention to the phenonium-ion intermediate. What would be the difference in this diagram if the phenonium ion were a transition state instead of an intermediate?

Short Answer

Expert verified
In the reaction coordinate diagram for the solvolysis of 2,2,2-triphenylethyl chloride in acetic acid, the phenonium ion intermediate is represented by an energy level above the reactants. The diagram has two energy barriers connecting the reactants, the phenonium ion intermediate, and the products. If the phenonium ion were a transition state instead of an intermediate, there would be no separate energy level for it, and there would be only one energy barrier between reactants and products. The transition state energy level would be at the highest energy point of the energy barrier.

Step by step solution

01

Understand the mechanism for the solvolysis of 2,2,2-triphenylethyl chloride in acetic acid

First, we need to understand the mechanism for the solvolysis of 2,2,2-triphenylethyl chloride. In this process, the chloride anion leaves, generating a phenonium ion intermediate. The solvent (acetic acid) then attacks the phenonium ion and is deprotonated, leading to the formation of a product.
02

Draw the reactants, intermediates, and products of the reaction

Draw the structure for 2,2,2-triphenylethyl chloride, the phenonium ion intermediate, and the final product resulting from the solvolysis in acetic acid. #for the Phenonium ion intermediate, \[ C_{c_1} = charged carbon (c_1) \] #for the Product, \[ C_{c_1}OH = product \]
03

Draw the reaction coordinate diagram

To draw the reaction coordinate diagram, we will plot the energy levels of the reactants, intermediates, and products along the reaction coordinate. Label the axes as "Energy" on the vertical axis, and "Reaction Coordinate" on the horizontal axis. 1. Plot the energy level of the reactants (2,2,2-triphenylethyl chloride) on the left side of the diagram. 2. Plot the energy level of the phenonium ion intermediate above the reactants. 3. Indicate an energy barrier (activation energy) for the conversion from reactants to the phenonium ion intermediate. 4. Plot the energy level of the products after the solvent has attacked and deprotonated the phenonium ion. 5. Indicate an energy barrier (activation energy) for the conversion from the intermediate to the products.
04

Compare the diagram with and without a transition state

Now, we will discuss the difference in the diagram if the phenonium ion were a transition state instead of an intermediate. In this case, we would not have an energy level for an intermediate between the reactants and the products. There would be a single energy barrier between the reactants and the products, representing the activation energy for the reaction. The transition state energy level would be at the highest energy point of the energy barrier.

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