Problem 2: Kinetic versus thermodynamic controls Chemistry is controlled by what is most stable product (thermodynamics)

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Problem 2 Kinetic Versus Thermodynamic Controls Chemistry Is Controlled By What Is Most Stable Product Thermodynamics 1 (52.39 KiB) Viewed 39 times

Problem 2: Kinetic versus thermodynamic controls Chemistry is controlled by what is most stable product (thermodynamics) and by how fast is a reaction (kinetics). Loss of bromine from 6-bromohexane leads initially to hex-5-enyl radical. Rearrangement of the later results in cyclohexyl and cylopentylmethyl radicals, as show below. Chemists easily recognize that cyclohexyl radical is more stable than cylopentylmethyl radical (why?). Examine structures and energies of both radicals. Which radical is more stable (lower energy)? Recall that an energy difference of 12 kJ/mol corresponds to a product ratio of >99:1. Do you conclude that ring closure is under thermodynamic control? Buy Sinh AIBN 17% Rearrangement Ed-g 81% The next objective is to establish which ring closure, to cyclohexyl radical or cylopentylmethyl radical is easier; that is, which product, cyclohexane or methycyclopentane, is the kinetic product? Bring up calculated structures and energies for the transition states for the two ring closures. Optimize hex-5-enyl radical and calculate AE*. Which radical, cyclohexyl or cylopentylmethyl, is more easily formed (has lower AE¹)? Do you conclude that ring closure is under kinetic control?