HT2-05ans - Answers to Hour Examination#2 Chemistry...

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Answers to Hour Examination #2, Chemistry 302X-302A, 2005 1. (a) Aldol followed by reductions: 1. H 3 O + /H 2 O (aldol) 2. H 2 /Pd/C (reduce) 3. NH 2 NH 2 /HOCH 2 CH 2 OH/heat (Wolff- Kischner - you could also use the Clemmenson) or 1. LiAlH 4 2. H 2 O 3. HBr 4. Li (makes cyclohexyllithium) 5. react with cyclohexanone 6. H 2 O/H 3 O + (protonate and eliminate). 7. H 2 /Pd/C (b) Aldol followed by Michael: 1. H 3 O + /H 2 O 2. KCN, H 2 O (c) Knoevenagel: 1. (CH 3 OOC) 2 CH 2 /CH 3 O Na + 2. neutralize 2. (a) 1. LDA 2. CH 3 I (an enamine process is also fine) (b) 1. CH 3 Li 2. H 2 O 3. H 3 O + /H 2 O (E1) 4. BH 3 5. HOOH/HO 6. KMnO 4
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O N H H 3 O + 1 (C 14 H 17 N) Br 1. 2. H 2 O 2 (C 13 H 14 O) (Ph) 3 P=CH 2 3 (C 14 H 16 ) heat N O CH 2 (Wittig) (enamine formation) Cope 4. It is clear where the new bond joining the two pieces must be formed. H O + CH 3 O OH O CH 2 CH 3 But it is equally clear, we hope, that there is no acidic hydrogen available for removal. CH
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This note was uploaded on 03/07/2010 for the course ORGO 1 AND V.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT2-05ans - Answers to Hour Examination#2 Chemistry...

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