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Linda%20worksheet%20week%2011 - N H O O O A B 4 Draw a...

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1. Give the mechanism and predict the products of the following reactions. a) O 1. Na C CH 2. HCl/H 2 O b) O HCN H 3 C O N H H 3 C O O 2. Rank the following molecules in order of increasing acidity of the alpha hydrogens. (1=most acidic, 2=less acidic, 3=least acidic) Hint: Draw the second best resonance contributors for each molecule in its deprotonated form after one of the alpha hydrogens has been removed. H 3 C O H H H Chemistry 232 SI Week 11 Linda Johnson: [email protected] AIM Screen Name: Chem232Linda Key Concepts pages 133-154 - Carbonyl Chemistry - Acidity of alpha hydrogens Most Imp. Homework Problems: Ch. 16 #4, 5, 14, 19, 20, 31, 33 Ch. 17 #5, 10, 13, 17, 23, 31, 42, 44, 47 (5 th Edition)
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3. Which carbonyl is the stronger base? *Hint: Consider resonance structures of the protonated forms.
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Unformatted text preview: N H O O O A B 4. Draw a reaction coordinate diagram using your answers from #6. H H 5. Propose a mechanism to the following reaction. O O O CH 3 MgBr O O OH CH 3 MgBr Product A Product B Product A Product B H 6. Propose a mechanism for the following reaction. O O (C 6 H 5 ) 3 P CH 2 CH 2 O (C 6 H 5 ) 3 P O First consider the resonance structures of the phosphonium ylide. (C 6 H 5 ) 3 P CH 2 Resonance Contributor A Resonance Contributor A Product Product Check out this website for some extra help with organic chemistry: http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm...
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