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chm 2120 answers 5 - Answers Assignment#5/CHM 2120 05 1 H3C...

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Answers, Assignment #5 /CHM 2120/ 05 T. Durst 1. CH 3 H 3 C CH 3 S N N N N CH 3 N N NH H no yes no yes yes yes yes no yes no 2. Cl AlCl 3 Complexation between AlCl, a strong Lewis acid and 1-chloropropane leads to .. Cl AlCl 3 δ + δ - This species can be attcked in the usual way be the pi elelcrons of the benzen ring to give propyl benzene. The polarized intermediate is almost a primary cation, it can rearrange to forma a more stable isopropyl cation which then reacts with benzene to give the isopropyl benzene H H 3 C H 3 C H (+) AlCl 4 (-) 3. Complexation between the AlCl 3 and the FeCl 3 or AlCl 3 leads to an incipient primary carbocation that rearranges to a secondary one. Same as above CH 3 H (+) CH 3 H H (+) loss of a beta H leads to re-aromatization and the product 4 a) O only the para isomer. The reagent is very bulky and thus no , or very little ortho isomer forms 5 OCH 3 OCH 3 H 3 C CO 2 H CH 3 OCH 3 Cl CO 2 H NO 2 +++ +++ and + --- and + +++ and - --- and --- fastest slowest
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6 CO 2 H OH OH OCH 3 NO 2 OH OH F most acidic is the carboxylic acid least acidic the aliphatic alcohol
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