F.07.210.E3F - Name Page 1 F.07.210e3p1 I(28 points(a A...

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Name _______________________ Page 1 F.07.210e3p1 I. (28 points) (a) A clever Chem 211 student decided to try and carry out the following transformation in order to impress Dr. Nolta! C C H 1) LiH 2) Br C C Unfortunately, the reaction failed completely! In a few words, tell the student what the major error was in this plan. (b) Compound K Compound N What is the IUPAC name for Compound N ? (c) Compound N can actually be prepared from the corresponding alkene, in a two step sequence. Draw the result of the bromination reaction (if racemic, draw one enantiomer and write "plus enantiomer," if meso, draw it and write "meso," if diastereomers, draw one and write "plus diastereomer(s)," and if there is only one compound with no stereoisomers, then just draw it). Complete the reaction scheme as required. C C C H H Br 2 CCl 4 (d) Complete the following. In the second step, a reagent that is the direct analogy of OsO 4 is used; predict and draw out its Lewis structure as your answer. C C C C H H C C H H HO NH 2 racemic 4 6 6 4 4 4 The bromobenzene (PhBr) cannot participate in simple substitution reactions because the Br atom leaving group is on an sp 2 carbon 4 pts for the reason that S N cannot occur at the sp 2 C -2 for extraneous incorrect information 1,2-diphenylethyne -2 per type of error punctuation, numbering, root name, suffix C C H H Br Br meso connectivity = 2 stereochem = 3 'meso' = 1 excess or 2 equivs of some base w/ conj acid pKa > 15 2 CH 3 CH 2 OLi no partial; stoich not required H 2 Pd, Pd-BaSO 4 or Pd-CaCO 3 plus PbO or quinoline H 2 = 2 poison cat. = 2 Os O O O NH no partial
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Name _______________________ Page 2 F.07.210e3p2 II. (29 points) A. (a) The following electrophilic addition reaction is highly regioselective. Draw the expected product(s) (if racemic, draw one enantiomer and write "plus enantiomer," if meso, draw it and
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This note was uploaded on 04/02/2008 for the course CHEM 210 taught by Professor Capolla during the Fall '07 term at University of Michigan.

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F.07.210.E3F - Name Page 1 F.07.210e3p1 I(28 points(a A...

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