Consider a fluorine radical generating a radical from butane.Predict whether the transition state is reactant-like or product-like and justify your answer. Use the the following bond-dissociation enthalpies.

Which of the given electrophilic addition reactions would you expect to be more selective toward the carbocation formation? Explain your answer.

The more stable 3° carbocation forms faster than the 2° carbocation as shown below. Draw a reaction coordinate diagram illustrating that the most stable intermediate forms first.

Determine the most likely transition state for the given conversion. Explain your response.

Deuterium (D) is the hydrogen isotope of mass number 2. Deuterium shows almost identical chemistry to that of hydrogen, except that C−D bond is slightly stronger than the C−H bond by 5.0 kJ/mol, so that when a C−D bond is broken in a rate-limiting step, the reaction rate tends to be slower (as opposed to a C−H bond), an effect called a kinetic isotope effect.

When the chlorination of methane was compared to that of propane, experimental results showed that methane has a much larger isotope effect than propane. Consider the thermodynamics of the chlorination of methane and the chlorination of propane and explain this phenomenon using the Hammond postulate.

The isotope of hydrogen with mass number 2 is called Deuterium (D). The C―D bond is slightly stronger than the C―H bond and because of this, reaction rates tend to be slower when a C―D bond is broken in a rate-limiting step compared to a C―H. This effect, called a kinetic isotope effect, is observed in the comparison of the bromination of methane and tetradeuteriomethane. Provide the transition state for the rate-limiting step of each of these reactions.