Can you help answering these questions based on the provided data? Please explai

Question

Can you help answering these questions based on the provided data? Please explain the reasons

Questions Based on your calculated reaction barrier energies, which carbon environment would you expect to be most reactive with respect to the following? a. SN1 reactions b. SN2 reactions 1. 2. Based on your calculated reaction barrier energies, which carbon environment would you expect to be least reactive with respect to the following? a. SN1 reactions b. SN2 reactions 3. With regard to Questions 1 and 2, what kinds of chemical effects (e.g. steric effects, carbocation stability, etc.) influence the following? a. SN1 reactivity b. SN2 reactivity 4. How do your calculated energy barriers compare to those done by your classmates? Which leaving group (X) had, on average, the lowest energy values? Which leaving group (X) had, on average, the highest energy values? What does this imply about the reactivity of your leaving group (X)? a. b. C.

Explanation / Answer

1. For this lowest energies are considered.

SN1 - Tertiary and Iodine substituted compounds follows SN1.

SN2-Ptimary and Iodine substituted compounds follows SN2. more easily

2.

For leat reactive substrate, highest energy is considered

SN1-Primary and Iodine substituted compound, SN1 barrier is the maximum.

SN2- Tertiary and Chlorine substituted compound, SN2 barrier is the maximum.

3.

SN1 reactivity- The stability of the carbocation and the nature of the leaving group determines the energy barrier.

Tertiary carbocations are stable than secondary and primary due to +I effect of alkyl groups. Thus, SN1 is followed by the tertiary compounds. Iodine is the best leaving group and thus Iodo substituents are having lower energy.

SN2 reactivity. In this case, steric hindrance matters. Tertiary compounds are sterically hindered whereas primary compounds are less hindered. Thus Primary compounds follows this mechanism. In this case also, leaving group matters. Iodine is the best leaving group and thus Iodo substituents are having lower energy

4.

a. Iodine

b. Cl

c. The leaving group should be able to stabilize the negative charge after the bond breaking. Iodine is a big atom and it can hold the negative charge more than the Cl and Br. (kindly note that HI is the strongest acid due to the same reason)

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