Midterm_1_practice_KEY

Midterm_1_practice_KEY - Chemistry 140C(Finn Spring 2008...

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Chemistry 140C (Finn) Spring 2008 – Practice Problems for Exam 1 – Answers (with extra explanations in most cases) 1. Treatment of ketone 1 with base in ethanol- d 1 gives a single deuterated product. Draw the structure of that product, and write a detailed, arrow-pushing mechanism for its formation. If steps are repeated, just write “repeat,” rather than write them out again. O H 3 C NaOEt (catalyst) deuterated product H 3 C CH 3 1 CH 3 CH 2 OD (solvent) O D 3 C H 3 C CH 3 D D O C H 3 C CH 3 H H H EtO O C H 3 C CH 3 H H D EtO NaOEt EtOD O C H 3 C CH 3 H H D repeat previous two steps O C H 3 C CH 3 D D D H H NaOEt EtO O C H 3 C CH 3 D D D H D EtO EtOD O C H 3 C CH 3 D D D H D O C H 3 C CH 3 D D D D D I've re-drawn the first enolate here D OEt O C H 3 C CH 3 H H EtOD O C H 3 C CH 3 H H H D NaOEt OEt O C H 3 C CH 3 H H D reacts as above Note that you can't deprotonate this proton directly, but if you get to the enolate by deprotonating at the ! position, the exchange occurs as shown here. I'm sorry - I failed to point out this kind of exchange in the answer to Quiz 1. .. O H 3 C H 3 C CH 3 H
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Page 2 of 6 2. Write the structure of A in the box and circle the proper final structure. Then write a
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This note was uploaded on 06/07/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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Midterm_1_practice_KEY - Chemistry 140C(Finn Spring 2008...

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