Final ans 2005 - Answers to Chemistry 302X-302A Final...

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Unformatted text preview: Answers to Chemistry 302X-302A Final Examination, 2005 1. O H H 3 C OH C O + O CH 2 CH 3 O In the plane of the ring, does not overlap with the carbonyl pi bond- hence, no resonance stabilization, and no acidity of this hydrogen H 3 C O C O + HOCH 2 CH 3 (a) (b) O H H H (c) p K a = 4.76 p K a = 16 2. O CH 3 OH O O H H HOH 2 C H 3 C H H O O O CH 2 OH H 3 C O O O H H H H OH CH 3 O O O O O O H H CH 2 OH H 3 C H H note endo arrangement for Diels-Alder = = addition- elimination 3. H 3 C O OH RO ROH H 3 C O O H 3 C O O H 3 C O O H 3 C O O H 3 C O O reverse "aldol" () () note res. stabilization protonate deprotonate Michael protonate and you are done 4. O O O O NaOCH 3 /HOCH 3 O O O O O O O O O O aldol- eliminate just a Robinson annelation.... protonate- deprotonate Michael 5. (a) First convert PhCH 2 CH 2 OH into the corresponding acid (KMnO 4 ), then make the acid chloride with SOCl 2....
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Final ans 2005 - Answers to Chemistry 302X-302A Final...

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