Midterm 3 - Midterm 3 Chem 0320 9:00 AM9:50 AM April 2 2008...

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page 1 Midterm 3 Chem 0320 9:00 AM–9:50 AM April 2, 2008 Answer Keys 1. Circle the most reactive molecule in nucleophilic addition-eliminations. [3 points] O O O O CF 3 O N H O N H CF 3 2. (a) The reduction of A by LiAlH 4 followed by aqueous workup gives B . Circle hydrogen atom(s) derived from LiAlH 4 . [4 points] (b) What is the major product when A is treated with CH 3 Li followed by D 3 18 O + ? [5 points] CN LiAlH 4 then H 2 O N H H H H A B CH 3 Li; then D 3 18 O + 18 O 3. Circle the most basic amine. [4 points] N N N N DBU (middle) See textbook p994 4. Propose an efficient synthesis of D from C using a reducing agent. [8 points] OH N PCC O NH NaBH 3 CN OH N CrO 3 , H 2 SO 4 , H 2 O OH NH O heat N O LiAlH 4 SOCl 2 or PBr 3 X O NH
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page 2 5. Provide a reagent for the following conversion. [4 points] Cl O O Me 2 CuLi 6. Provide the structure of the major product. Assume that all the reactions involve aqueous workup with H 2 O. [4 points each] (a) (b) OEt O OH excess MeMgCl N OEt O LiAlD 4 N OH D D (c) at room temperature (d) O O O EtNH 2 O N H CO 2
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