CH310N_Spring09_HW05_1 - products Denote a chiral center...

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Sessler CH310N Homework Problem Set 5 Due Thursday, March 5th 1 K E Y Please write the first three letters of your last name in the above boxes Name:_______________________________ UT EID:_____________________________ Signature:____________________________ Score:___________/76 __ 1. Fill in the empty boxes with appropriate chemicals/conditions (8 points). O OH N H 2 , Ni O NH 3 CH 2 - - P + Ph 3
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Sessler CH310N Homework Problem Set 5 Due Thursday, March 5th 2 2. Draw the detailed mechanism (arrow pushing) for the acid catalyzed formation of acetone diethyl acetal from acetone and ethanol. (10 points) 3. Propose a synthetic scheme that allows for the preparation of 5-hydroxy-5phenylpentanal from benzaldehyde and 4-bromobutanal (Hint: Read chapter 16 in the book carefully). (10 points)
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Sessler CH310N Homework Problem Set 5 Due Thursday, March 5th 3 4. Complete the following reactions by filling in the boxes with the missing reactants, conditions or
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Unformatted text preview: products. Denote a chiral center with an asterisk in the product structures if relevant. (15 points) O O 1. LiAlH 4 2. H 2 O H 2 , Rh O OH O O Zn(Hg), HCl N 2 H 4 , KOH, 200 o C NaBH 4 Sessler CH310N Homework Problem Set 5 Due Thursday, March 5th 4 5. Give a detailed mechanism (arrow pushing) for the Wolff-Kishner reaction to reduce ketones. (10 points) 6. Propose one or two step routes to the following deuterated alcohols starting from diethyl ketone and any kind of deuterium-containing inorganic materials. (8 points) OH HO O D D D D D Sessler CH310N Homework Problem Set 5 Due Thursday, March 5th 5 7. Complete the following transformations by filling in the empty boxes. (15 points) O O O O H H Br Br Br Br AgNO 3 , NH 3 , H 2 O OH O O O HN H 2 N H + H +...
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