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Final - Fall 200605 - structures drawn below a b c d e...

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5 10 - 11. The following reagent list applies to questions 10-11 . a) NaNH 2 /NH 3 f) BH 3 ; H 2 O 2 / HO b) H 2 /Pd/C g) POCl 3 /pyr c) NBS/H 2 O/DMSO h) H 2 /Lindlar’s catalyst d) CH 3 OH/heat i) Li/NH 3 (liquid) e) Hg(OAc) 2 /H 2 O; NaBH 4 j) H 2 SO 4 /SO 3 What are the correct reagents necessary to carry out each transformation? 10 . (4 pts) Br Answer: a 11 . (4 pts) OH Br Answer: c Comments: These questions test for knowledge of reactions/reagents. There are examples of this type of questions in the practice set: TS4: 36, 71, 72, 73, PE4A: 30, PE4C: 8, 15-18). Question 10 is a simple elimination that requires strong base. Question 11 is a formation of bromohydrin. 12. (4 pts) Which symbol should be used to correctly represent the relationship between the two
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Unformatted text preview: structures drawn below? ? a) b) c) d) e) Comments: This question was about understanding resonance, and not confusing it with carbocation rearrangements. The structures differ only in position of π electrons (which by definition is resonance). None of the atoms change position (which would be required in a carbocation rearrangement). There was no direct precedent for this question, but it tests a very basic concept. All questions on 1,2- vs. 1,4- electrophilic addition require understanding of that concept....
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