(Solved): In both examples below the reactants shown are combined to bring about a nucleophilic substitution ...

In both examples below the reactants shown are combined to bring about a nucleophilic substitution $\left({\mathrm{S}}_{N}1,{\mathrm{S}}_{N}2\right)$ and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case? Draw both resonance structures for the radical produced by reaction of the compound with bromine atom. Assume reaction occurs only at the weakest $\mathrm{C}-\mathrm{H}$ bond. - You do not have to consider stereochemistry. - You do not have to explicitly draw H atoms. - Separate resonance structures using the symbol from the drop-down menu. - Include all valence radical electrons in your answer. Accepted names for branched alkyl groups are isopropyl, isobutyl, sec-butyl, and tert-butyl. 1. $\underset{\mathrm{DMSO}/{\mathrm{H}}_2\mathrm{O}}{⟶}$ 2. $\mathbf{a}=$ Proton transfer $\mathbf{d}=$ Electrophilic addition $\mathbf{g}={\mathrm{S}}_{\mathrm{N}}1$ Nucleophilic substitut $\mathbf{b}=$ Lewis acid/base $\mathbf{e}=$ E1 Elimination $\mathbf{h}={\mathrm{S}}_{\mathrm{N}}2$ Nucleophilic substitut $\mathbf{c}=$ Radical chain substitution $\mathbf{f}=$ E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters $\mathbf{a}$ - i for your answers. 1. 5.