Problem: A graduate student was attempting to functionalize an alkane for a research project to make her advisor happy. While characterizing the products of her radical bromination reaction, she isolated the byproduct 2,3,3,4,4,5-hexamethylhexane (below). Please answer the following questions concerning the radical reaction. a. Provide the overall reaction scheme for the desired radical bromination. You will need to determine what the starting materials were, reaction conditions, as well as the major products. b. Provide a detailed mechanism including all three parts of radical bromination to show how the isolated side product 2,3,3,4,4,5-hexamethylhexane was formed. c. Other than resonance, what explains the stabilization of alkyl radicals? Provide the name of this stabilization and using both pictures and words, explain this term.

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A graduate student was attempting to functionalize an alkane for a research project to make her advisor happy. While characterizing the products of her radical bromination reaction, she isolated the byproduct 2,3,3,4,4,5-hexamethylhexane (below). Please answer the following questions concerning the radical reaction.

a. Provide the overall reaction scheme for the desired radical bromination. You will need to determine what the starting materials were, reaction conditions, as well as the major products.

b. Provide a detailed mechanism including all three parts of radical bromination to show how the isolated side product 2,3,3,4,4,5-hexamethylhexane was formed.

c. Other than resonance, what explains the stabilization of alkyl radicals? Provide the name of this stabilization and using both pictures and words, explain this term.

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