Answer to Question #301920 in Organic Chemistry for Karly

Question

2.3 Assuming that the nitrogen in enamine is sp2 hybridized, explain why the double bond of

an enamine is more nucleophilic than a typical alkene double bond.

3.2 The reaction of methylpropene with HBr, under radical conditions, gives two

intermediates. Propose a mechanism for the formation of the two products.

3.4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures

to account for its stability

Answer 1

2.3) This is because the double bond of an amine is electron rich and the carbon atom and nitrogen atom are all sp-2 hybridized so the p orbital will form π3 4 conjugated system, the electrons are delocalized and will surely lower system's energy and make it more nucleophilic.

3.4) Antioxidants compounds are hydrogen atom transfer (HAT), single electron transfer (SET) and the ability to chelate transition metals.

Vitamin E molecule structure is comprised of a chromanol ring with a side chain located at the C2 position.