2006spring-midterm02solns

2006spring-midterm02solns - ! Chemistry 140C (Tor) Spring...

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Chemistry 140C (Tor) Spring 2006 – 2nd Midterm Exam (V.1) 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 ethoxide in ethanol, followed by a reaction with ethyl acrylate (compound 2 ) gives product 3 : OEt O O 1 3 O O OEt O OEt O 1. EtO ! Na + 2. 2 EtOH EtOH Write a detailed stepwise mechanism that accounts for the formation of 3 . O 1 3 O OEt O OEt O O H H OEt O O O O EtO O O O O H EtO EtO O OH O EtO O Et O H O O EtO O Intramolecular mixed Claisen Conjugate (Michael) addition EtO
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Name: ________________________ ID# _________________ 05-23-06 3 2. When the dicarboxylate salt 4 is heated up in acid as shown below, cyclopentanone 5 is formed: O O O !
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2006spring-midterm02solns - ! Chemistry 140C (Tor) Spring...

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