Midterm_1_practice

Midterm_1_practice - Chemistry 140C(Finn Spring 2008...

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Chemistry 140C (Finn) Spring 2008 – Practice Problems for Exam 1 Here are some problems that didn’t make it onto the test. I will post the answers this weekend. 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) Mechanism:
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Name: ________________________ 04/23/08 Page 2 of 5 2. Write the structure of A in the box and circle the proper final structure. Then write a detailed, arrow-pushing mechanism for the formation of A . O Ph MeO + N H CH 3 CO 2 H (cat.) toluene, -H 2 O 1) PhCHO t-BuOH 2) HCl (cat.) H 2 O A O O MeO Ph Ph N Ph MeO OH Ph O O MeO Ph Ph O Ph MeO OH Ph Mechanism:
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Name: ________________________ 04/23/08 Page 3 of 5 3. Circle the more acidic molecule in each pair. O H 3 C CH 3 O F 3 C H O H 3 C CH 3 O Cl 3 C CH 3 O H 3 C OH S O HO OH O R NH 3 R OH 4. Circle the most likely product of the indicated reaction. (In some cases, you haven’t seen the exact reaction before, but see if you can make an analogy to something you
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