Assignment_4_2008 - CHM 1321 Assignment 4 In this...

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CHM 1321 Assignment 4 In this assignment: - Acid/base reactions - Resonance 1) Draw the important resonance forms and show the resonance hybrid structures for the following: H 3 C C CH 3 O (a) H 3 C C CH 2 O (b) (c) (d) H 3 C C NH 2 O (e) H 3 C C C H 2 OH CH 3 (f) HC HC C H CH C H C CH 2 (g) H 2 CCH 2 CH S H 2 C (h) N CH 3 H 2 CC H 3 (i) CH 3 NO 2 (j) CH 3 COOH HC HC C H CH C H C CH 2 2) For the following, label the major and minor resonance forms, and show which ones are of equal energy. Briefly justify your choices. H 3 C H CCN H 3 C H (a) (b) H 3 C C C H O H C CH 3 H 3 C C C H O H C CH 3 H 3 C C C H O H C CH 3 (c) H 3 C C C H C H 2 CH 3 OO H 3 C C C H C C H 2 CH 3 H 3 C C C H C C H 2 CH 3 (d) H 3 C H 2 C C NH 2 NH 2 H 3 C H 2 C C NH 2 NH 2 H 3 C H 2 C C NH 2 NH 2
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Assignment 4 2 3) For each pair of ions, determine which is more stable. Justify your answer in each case. H 3 C H C CH 3 or H 3 C H C OCH 3 (a) (b) H 2 C H C H C CH 3 or H 2 C H C H 2 C CH 2 (c) CH 2 CH 3 or CH 2 CN (d) H 2 C H 2 C C H 2 CH C H 2 C CH 2 or H 2 C H 2 C C H CH CH H 2 C CH 2 (e) N C H 3 CC H 3 H 3 H 3 or CH C H 3 H 3 H 3 H 3 (f) or CH 3 CH 2 O CH 3 CO 2 (e) HC HC C H CH C H C CH 2 or H 2 C H 2 C C H CH CH H 2 C CH 2
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Assignment 4 3 4) For the following pairs of compounds, predict which one will be the strongest acid
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Assignment_4_2008 - CHM 1321 Assignment 4 In this...

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