Examination%20_1%20Spr%202008

Question115points

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Unformatted text preview: you wish to have graded. Otherwise, I will grade the fist answers I see. Question 1 (15 points) Provide systematic names for three of the following five compounds. O2N 1‐isobutyl‐2‐methyl‐4‐nitrobenzene 1‐(2‐methylpropyl)‐2‐methyl‐4‐nitrobenzene Br Cl CH3 2‐bromo‐1‐chloro‐4‐methylbenzene 3‐bromo‐4‐chlorotoluene Br p‐dibromobenzene 1,4‐dibromobenzene Br OH 2,4,6‐trimethylphenol NH2 Cl 2‐chloroaniline o‐chloroaniline Question 2 (12 points). Predict, with reference to the relevant reaction mechanism, the outcome of the following reaction (including stereo‐ and regiochemical outcomes). You must include the detailed reaction mechanism in your answer, and may include other structures or diagrams to explain your answer. NBS, hν NBS generates small amounts of Br2 in situ on reaction with HBr. CCl4 hν Br-Br CCl4 Br* is highly selective due to the endothermicity of the hydrogen abstraction step (the rate limiting step). Due to the symmetry of the molecule, abstraction at any of the secondary allylic sites will generate the same product distribution. HH Br The allylic radiacl is planar. Thus, bromine may attack from either face of the molecule in the second step, leading to pairs of enantiomers. 2 Br Hydrogen atom abstraction occurs at the secondary allylic site to generate a resonance stabilized allylic radical. The free electron is delocalized with partial spin density on secondary and tertiary sites. Reaction at both sites is possible. + H HBr + Br Br Br Br + Br Br Br Br + Br + B...
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This note was uploaded on 10/28/2010 for the course CHEM 235 taught by Professor Dr.poole during the Spring '10 term at Ball State.

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