CHEM 3580- PPS#2 solutions.pdf

CHEM 3580- PPS#2 solutions.pdf - C3580 PPS#2 Solutions Page...

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C3580 PPS#2 Solutions Page 1 of 8 1) Label the following compounds (or ions) as aromatic ( A ), non-aromatic ( N ), or anti- aromatic ( AN ). + + - - + - A AN AN A A A A AN N N A A N A AN N N N N
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Page 2 of 8 2) For each compound, ion, or radical species below, label it as A (aromatic), N (non- aromatic), or AN (anti-aromatic). Write your answer on the line below each. : : N + H N + H N N H H N NH N HN + : N N N H N NH 2 NH N H O - O - + + : A A A A A A A A A N AN N
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Page 3 of 8 3) For each compound, ion, or radical species below, label it as A (aromatic), N (non-aromatic), or AN (anti-aromatic). Write your answer on the line below each. 4) C + H C - H N N N H N NH 2 NH N H O O C + H CH 3 I I H 3 C C + H A N AN A A A (OR N) A (OR N) A N A N N H 3 C O Cl Al Cl Cl Cl H 3 C O Cl + Al - Cl Cl Cl Br C + Br C H 3 C - O Cl + Al - Cl Cl Cl H H C + Br C H 3 C O H H Cl Al - Cl Cl Cl Br O H 3 C
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Page 4 of 8 5) 6) O Br Fe Br Br Br O Br + Fe Br Br Br - C + H H O Br Fe - Br Br Br O Fe Br Br Br Br Br Br Br + Fe - Br Br Br C + Br H H Br Fe - Br Br Br Br
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Page 5 of 8 7) H O N + O O - H O S O O O H H O + N + O O - H N + O O CH 3 C + N + O O - H H CH 3 - O S O O O H CH 3 NO 2 Repeat two more times at ortho positions! Each nitro group addition further deactivates the ring toward the addition of the next nitro group.
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Page 6 of 8 8) Al Cl Cl Cl
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