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Practice_Aromatic Chemistry_Answer

Practice_Aromatic Chemistry_Answer - Cl Cl Cl 1 AlCl 3 2...

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1. Aromaticity 2. Predict the trend in acidity for the following substituted phenols. Rank by increasing acidity and explain. Trend: B A D C A B C D 3. Draw the relative energies for the molecular orbitals of the cyclooctatetraenyl dianion. Predict the stability of this species: OH OH OMe OH NO 2 OH NO 2 π 1 π∗ 6 π 4 π 2 π 3 π 5 π∗ 7 π∗ 8 Compound π electrons aromaticity 2 Aromatic 6 Non-aromatic 8 Anti-aromatic 4 Anti-aromatic 6 Aromatic B N N H
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4. Predict the products: 1. HCOCl, AlCl 3 2. Ph 3 P=CH 2 1. H 3 PO 4 , CO 2 H H 2 N CO 2 H H 2 N O O CO 2 H 1. FeCl 3 , Cl 2 2. NaOH, H 2 O, high pressure, heat 3. H 3 O + 4. NaOH, H 2 O; CO 2 5. HCl, H 2 O 6. Ac 2 O O O O 1. Benzene, AlCl 3 2. Zn(Hg), HCl, Heat 3. SOCl 2 4. AlCl 3 5. HNO 3 , H 2 SO 4 O O 2 N NH 2 1. NaNO 2 , H 2 SO 4 2. H 2 O, Heat 3. NaOH, H 2 O 4. 5. H 3 O + O O OH NO 2 F KOCH 3 , 70 o EtOH F F F F OCH 3 NO 2
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5. Provide reagents for the transformations: Cl Cl NH 2 1. Cl 2 , FeCl 3 2. HNO 3 , H 2 SO 4 3. Cl 2 , FeCl 3 4. Fe, HCl Cl H N O 1. HNO 3 , H 2 SO 4 2. Cl 2 , FeCl 3 3. H 2 , Pd-C 4. CH 3 CH 2 COCl 1. HNO 3 , H 2 SO 4 2. Cl 2 , FeCl 3 (xs) 3. Fe, HCl 4. NaNO 2 , H 2 SO 4 5. CuCl Cl Cl
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Unformatted text preview: Cl Cl Cl 1. AlCl 3 2. FeCl 3 , Cl 2 3. N 2 H 4 , KOH, Heat Cl O 1. AlCl 3 2. Zn(Hg), HCl, heat Cl O 1. HNO 3 , H 2 SO 4 2. KOH 3. Br 2 , FeBr 3 Cl OH Cl Cl Br NO 2 6. Remembering that AlCl 3 is a Lewis Acid, and the byproduct is hydrochloric acid, propose a reasonable mechanism for the following transformation: AlCl 3 , heat Cl O H O H O Cl O H O AlCl 3 Cl O H O AlCl 3 O H O O H O O H O H ClAlCl 3 Cl AlCl 3 O H O HCl AlCl 3 O H OH O H OH H H O OH H H O OH 2 H 2 O H 3 O + H 2 O H HCl HCl 7. Provide Conditions for the following: 8. Mechanisms + A + B + C + D Cl Cl OH AlCl 3 AlCl 3 H 3 PO 4 H 2 SO 4 Cl N NH 2 NO 2 NH 3 NH 3 Cl N O O O O H 3 N NH 3 Cl N O O H 2 N + NH 4 + CH 3 KNH 2 liquid NH 3 Cl NH 2 CH 3 CH 3 + NH 2 H NH 2 CH 3 NH 3 Cl-NH 2 A B B A CH 3 CH 3 NH 2 NH 2 NH 3 NH 3 NH 2...
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