Question
Organic Chemistry
1. Draw each one of the following molecules and label it as: alkyl halide, allyl halide or vinyl halide
a) 2-chloro-3-ethylpentane
b) 6-ethyl-3-lodocyclohexene

2. Give all resonance structures of the allylic radical intermediate that arise from reaction above. All allylic C-H on the molecule are equivalent so only show the two resonance structures arising from one C-H bond reacting.

3. Are the resonance structures above equivalent or non-equivalent?

4. Give all the products expected from the reaction above.
Chem 227 Worksheet 9: Allylic Bromination and Organohalides (9 points) Draw each one of the following molecules and label it
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Answer #1

Allyl halide 6ethyl-3-iodocyclohexene Alkyl halide 2-chloro-3-ethylpentane HCCHE - H3C Y N- Br + H Br Br— Br + - trace amount

In above allylic bromination reaction using NBS and UV light free radical reaction two intermediates are formed shown by A and B

3. These two free radical intermediates are non-equivalent as in compound A free radical carbon is primary whitle in compound B free radical carbon is secondary.

4. Reaction between free radical bromine and free radical intermediate A gave (E)-1-bromobut-2-ene product while with ree radical intermediate B gave 3-bromo-2-methylbut-1-ene product.

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