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Exam1 3 an -09

Exam1 3 an -09 - Some Answers to exam 3 2009 1(a O(b OCH3 O...

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Some Answers to exam 3, 2009 1. O OCH 3 (a) (b) OCH 3 O 1. Full Eq. NaOCH 3 2. CH 3 CH 2 CH 2 CH 2 OTs 3. NaOCH 3 4. CH 3 I 5. H 3 O + /H 2 O From From (a) 1. LiAlH 4 2. pH = 7 3. TsCl 4. (CH 3 ) 3 CO 5. H 3 O + /H 2 O 6. NaOCH 3 or NaH 7. CH 3 I alkoxides come from the corresponding alcohols and NaH (or other good base) methyl iodide comes from methyl alcohol and HI Tosylate, ROTs from ROH + TsCl
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2. (a) (b) OH O OCH 3 O OCH 3 O OH O OH O OH O OCH 3 O Cl O Cl O NaOEt NaOH OCH 3 O 1. LiAlH 4 2. H 3 O + /H 2 O cat. NaOEt full eq. NaOCH 3 HOEt HOEt 1. full eq. NaOCH 3 2. H 3 O + /H 2 O to pH = 7 1. full eq. NaOCH 3 2. H 3 O + /H 2 O to pH = 1 NH 2 CH 3 1. CH 2 N 2 2. heat (c) (d) (e) (f) (g) (h) (i) (j) O O O O Na + Na + H 2 OR/HOR + OR O CH 3 CH 2 OH no product O O OCH 3 O O OCH 3 CH 3 O + CO 2 NHCH 3 O C O H 3 C
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3. 1. CH 3 CH 3 Cl AlCl 3 2. KMnO 4 C 7 H 6 O 2 1. SOCl 2. CH 2 N 2 C 8 H 6 N 2 O h ! C
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Exam1 3 an -09 - Some Answers to exam 3 2009 1(a O(b OCH3 O...

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