C c n h o h h h h 5 8 points draw the two most

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C C N H O H H H H 5. (8 points) Draw the two most important resonance contributing structures of the amide shown below. Be sure to show all lone pairs and formal charges. You do not have to draw arrows on this one. OH OH C) (5 points) In the space provided, draw the structure of the molecule as it would exist in water at pH = 1.0.
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Pg 3 _____________(21) Signature_________________________ 6. (6 pts) List two attributes of amide bonds that lead to stabilization of the folded structures of proteins. 7. (15 points) Aspartame is the sweetner used in diet coke. Its structure is shown below. Because of carbonation and added phosphoric acid, the pH of diet coke is relatively acidic, near 2.0. H 3 N H N O O O O O H CH 3 Aspartame B) (10 pts) Diet coke loses its sweetness over time, especially if heated. Can you suggest a likely reason for this based on the chemistry you have learned? We are only looking for two sentences or less here. A) (5 pts) For each bond indicated by the arrows on the above drawing, write "YES" or "NO" in the spaces provided to say whether the given bond can rotate (YES) or not (NO) at room temperature.
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Signature_________________________ 8. (23 points) In many of the mechanisms we have seen, there are charged intermediates encountered that are stabilized by resonance delocalization. For the following steps that come from different mechanisms, place arrows on the structures on the left to show the flow of electrons that lead to a charged intermediate. Next draw all the intermediates created as well as the indicated number of major contributing structures. Be sure so show all charges and lone pairs. Note, you only have to place arrows on the structures on the left side, not any of the contributing structures. F i n a l l y m a k e s u r e y o u s h o w a l l i n t e r m e d i a t e s m a d e i n t h e s t e p s i n d i c a t e d . Pg 4 _____________(23) N H O O H H H 3 major contributing structures C H 3 C N O H H H 2 major contributing structures A. B. C C C O H H H H H H C. O H 2 major contributing structures
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Signature_________________________ Pg 5 _____________(18) 10. (5 pts.) Rank the following in terms of anion stability, with a 1 under the anion that is the most stable and a 5 under the anion that is least stable. 12. (4 pts.) Rank the following in terms of anion stability, with a 1 under the anion that is the most stable and a 4 under the anion that is least stable. O O O Cl NH Please reread the directions to make sure you did not rank backwards! 11. (4 pts.) Rank the following in terms of reaction with a strong nucleophile such as HO-, with a 1 under the molecule that is most reactive , and a 4 under the molecule that is least reactive .
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