CHM 3120 Assignment 1b 2009

CHM 3120 Assignment 1b 2009 - a) O Ph H ? Ph O H b) O OEt O...

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CHM 3120 Assignment 1b Fall 2009 1. Predict the product(s) of the following reactions. a) b) c) d) EtO O O OEt 1) NaOEt, 2) NaOH, H 2 O 3) HCl, H 2 O 4) heat O Ph O OCH 3 2 eq. 1) NaOMe/MeOH 2) NaOH/H 2 O 3) H 3 O + /heat H 3 CO O O OCH 3 1) NaOMe MeOH 2) H 3 O + O H 1) BF 3 ·OEt 2 HS SH 2) BuLi 3) CH 3 I 2. What are the products that result from the following reaction? Draw the structures of the enolate(s) that are involved and denote the configuration of the enolates. O H 3 C H O + NaOH H 2 O
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3. Provide the missing reagents. (Hint: for (b) you will need another starting material).
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Unformatted text preview: a) O Ph H ? Ph O H b) O OEt O O OEt ? 4. Suggest a synthesis of the following molecules from the given starting material. Include all necessary reagents. a) O EtO O O OEt b) O O H 3 CO O O OCH 3 O + c) O EtO 2 C O CO 2 Et 5. How would you use a Robinson Annulation to make the following compounds? a) N CO 2 Et O O b) 6. Provide a multi-step retrosynthesis and forward synthesis for C starting from D and any starting material(s) you require. O O O OEt C D...
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This note was uploaded on 02/23/2010 for the course CHM Chm3120 taught by Professor Olgilvie during the Fall '09 term at University of Ottawa.

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CHM 3120 Assignment 1b 2009 - a) O Ph H ? Ph O H b) O OEt O...

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