2006spring-midterm02bsolns

2006spring-midterm02bsolns - Chemistry 140C (Tor) Spring...

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Chemistry 140C (Tor) Spring 2006 – 2nd Midterm Exam (V.2) This exam accounts for 30% of the final grade. Time 6:30 – 7:50 PM. Mark your final answer clearly and completely erase irrelevant information! Remember: Exams written in pencil will not be regraded! Additional pages are at the end for your convenience. Please indicate if your final answer should be found at the end of the exam. Good Luck! Your Name (Please Print): _________ KEY ______________ Your ID # : _____________________________ Question # 1:. .................................................................... /24 Question # 2:. .................................................................... /20 Question # 3:. .................................................................... /45 Question # 4:. .................................................................... /24 Question # 5:. .................................................................... /24 Question # 6:. .................................................................... /06 Question # 7:. .................................................................... /16 Question # 8:. .................................................................... /16 Question # 9:. .................................................................... /05 Total ................................................................................... /180
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Name: ________________________ ID# _________________ 05-23-06 2 1. Treatment of the ketoester 1 with sodium methoxide in methanol, followed by a reaction with methyl acrylate (compound 2 ) gives product 3 : OMe O O 1 3 O O OMe O OMe O 1. MeO ± Na + 2. 2 MeOH MeOH Write a detailed stepwise mechanism that accounts for the formation of 3 . O 1 3 O OMe O OMe O O H H OMe O O O O MeO O O O O H MeO MeO O OH O MeO O Me O H O O MeO O Intramolecular mixed Claisen Conjugate (Michael) addition MeO
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Name: ________________________ ID# _________________ 05-23-06 3 2. When the dicarboxylate salt 4 is heated up in acid as shown below, cyclohexanone 5 is formed: O O O ± Na + 4 H 3 O + H 2 O, ² + Na ± O O O 5 Write a detailed and stepwise mechanism that accounts for the conversion of 4 to 5 . O O O ± Na + 4 + Na ± O O O O H H H O H H H O O O O O H H Protonation OH O O H O H H H O O O H H Tautomerization O O O H O H H OH Tautomerization 5 Decarboxylation Decarboxylation O H H H O H O H H
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2006spring-midterm02bsolns - Chemistry 140C (Tor) Spring...

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