Organic Chemistry II - Test 2008 Section A

S e s carbon and nitrogen are in the same row of the

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s e s . - Carbon and Nitrogen are in the same row of the periodic table. - N i t r o g e n i s m o r e e l e c t r o n e g a t i v e t h a n c a r b o n and can s t a b i l i z e t h e n e g a t i v e c h a r g e b e t t e r - The equilibrium therefore lies toward the left (or: "favours reactants") 1 1 (must be stated or shown) 1 1 Note: a comparison of acids can be given, but pK a values must be cited. 4. a. Draw the mechanism and products for the following reaction. (5 points) b. Will the reaction favour starting materials or products? (1 point) c. Justify your choice in part b. (3 points) C H 2 C H pK a 25 pK a 38 The equilibrium lies to the r i g h t , toward the w e a k e r a c i d 1 1 1 1 (lone pair must be shown) 1 1 1 pK a must be within 5 units of correct value C H 2 C H H N N H
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