2006spring-midterm01-KEY

2006spring-midterm01-KEY - Name: _ ID# _ 04-25-06 1....

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Name: ________________________ ID# _________________ 04-25-06 2 1. Treatment of the ! , " -unsaturated ketone 1 with aqueous base facilitates an isomerization reaction to give product 2 : 1 !" ! # ! % " " " 2 Write a detailed stepwise mechanism that explains this transformation. ! ! ! ! " "! ! ! #$%&%’ )*&+,-%./0 /&*$%./ )%& 1/ 2’*.*&%./0 3’*4 1*.5 06’/).6*&7 " ! " " ! "
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Name: ________________________ ID# _________________ 04-25-06 3 2. For each one of the following reactions, circle the product that is preferentially formed. H O H O H O H OH (b) (c) (a) (d) H 3 O + , H 2 O O O HO O NaOH, H 2 O 5 0 C O H H O HO D 3 O + , D 2 O O D D O D D D D D D D O D D D D D 1. CH 3 CH 2 O ! Na + , CH 3 CH 2 OH, ! 5 o C 2. NaOH, H 2 O, " O O O O O O
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Name: ________________________ ID# _________________ 04-25-06 4 (e) (g) (h) 1. [(CH 3 ) 2 CH] 2 N ! Li + , ! 78 o C 2. CH 3 I O O O OH (f) O O O O OH O O OH O O O O OH O CH 3 CH 2 OH (large excess), H + O O O CH 3 OH, " OCH 3 O O HO OCH 3 O O H 3 CO OH O O HO CN O EtO HCl, H 2 O, " NH 2 O HO O EtO OH O
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Name: ________________________ ID# _________________ 04-25-06 5 (j) (i) O O H + HO O OH NaOH, H 2 O, " O O O O O ( ! H 2 O) O O O O O
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Name: ________________________ ID# _________________ 04-25-06 6 3. For each of the following pairs of compounds, decide which one is more acidic, and indicate it by using the symbol " > " (e.g., A > B for “ A is more acidic than B ”).
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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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2006spring-midterm01-KEY - Name: _ ID# _ 04-25-06 1....

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