Question

3. Based on your answer in 2. select the most likely reaction pathway. Explain how the substitution mechanism forms the product structure(s) shown. 2points А, H Br off and add NH toi O position because it Would Rick Ph Ph Ph- B H NH2 Ph Ph + NH 4. Identify the reaction components and solvents as more soluble in the aqueous (A) or organic (O) layer during separation of substitution and protonation steps. 3 pts Br HN НN CIO NH3 Bro A о

Answer 1

The alpha-halo substituted S_N2 reaction

In the given reactant have both pi-star orbital (carbonyl group) and sigma-star orbital (carbon- bromine bond). These two empty orbitals will overlap and give one lower energy orbital and one higher energy orbital. The newly formed lower energy orbital is lower energy LUMO than corresponding Pi-star LUMO or sigma-star- LUMO. So the incoming nucleophile HOMO can easily reach the lower energy LUMO. So the S_N2 reaction proceeds very faster rate than normal S_N2 reaction. For this reason, the given compound undergo S_N2 reaction faster Mannar.

This pi have corresponding pi-* orbital CH3 Ph + H HON H₂N Br This sigma bond corresponding sigma-* orbital

Mechanism:

H H BY ph backside attack ph NU NV 11 IZA phát + NP, Rhe # Br SNA Backside attack

Solubility:

Bro Y I

The First compound is quarternary ammonium salt which is ionic so this compound is more soluble in an aqueous layer in separation

The second compound is an organic amide which is less polar so which is more soluble in an organic layer in separation.

The third compound is an organic alpha-amino ketone which is more soluble in the organic layer in separation.

The forth compound is a quaternary ammonium salt which is ionic so this compound is more soluble in an aqueous layer in separation.

The fifth compound is an organic alpha-Bromo ketone which is more soluble in the organic layer in separation.

The last compound is well-known organic (DCM) solvent so this is soluble in the organic layer.