Wi00_final_v2 - NU, Winter2000, Final Exam 2 1. (40pts)...

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NU, Winter2000, Final Exam 2 1. (40pts) Complete the following series of reactions, be careful to give all the reaction conditions, starting materials, and all the major carbon-containing products. In electrophilic aromatic substitution reactions, shows only the mono-substitution product(s). Clearly indicate the stereochemistry when relevant. a) NC CN + b) Cl c) O MeC(O)Cl AlCl 3 d) OO H 3 O + in H 2 O e) OH O D D
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NU, Winter2000, Final Exam 3 f) I g) OH O h) 1) Br 2 , FeBr 3 2) HCl, CO, CuCl, AlCl 3 3) CrO 3 , 2 Py This is a partially trick question i) OsO 4 , H 2 O 2 C 10 H 18 O 2 H 2 SO 4 C 10 H 16 O IR spectrum shows an intense band at 1730 cm -1 j) 1) NaOMe, MeOH 2) H 3 O + Hint: The carbon carbon triple bond of alkyne can be both nucleophilic and electrophilic.
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NU, Winter2000, Final Exam 6 3. (20 pts) Draw the mechanisms for each of the following known reaction sequences using the electron-pushing curved-arrow formalism where possible. Indicate all the important proton transfer steps and show all the resonance-stabilized intermediates. Clearly indicate the stereochemistry when relevant.
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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Wi00_final_v2 - NU, Winter2000, Final Exam 2 1. (40pts)...

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