POW-310-12-Key - groups reinforce each other methoxy group...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for POW 310-12: Apr 20, 2009 3:00 PM Regiochemical Control: When using electrophilic aromatic substitution reactions, the regiochemical control of the final product can be achieved by the sequence of the steps. In the scheme below, provide the products and explain the regiochemical difference of the two final products. (Why is a different isomer formed in each sequence?) OCH 3 O OCH 3 NO 2 OCH 3 NO 2 HNO 3 H 2 SO 4 ClCOCH 2 CH 3 AlCl 3 OCH 3 ClCOCH 2 CH 3 AlCl 3 OCH 3 O OCH 3 O HNO 3 H 2 SO 4 NO 2 p is the major product- o position is sterically hindered by the methoxy group. methoxy group directs o, p, but the p site is blocked by the nitro group, which directs meta. The
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Unformatted text preview: groups reinforce each other. methoxy group directs o, p, but the p site is blocked by the acyl group, which directs meta. The groups reinforce each other. p is the major product-o position is sterically hindered by the methoxy group. Give the products of the sequence below. Where regioisomers are involved, use the major product or follow instructions below the box. CH 3 CH 3 NO 2 CH 3 NO 2 Cl COOH NO 2 Cl COCl NO 2 Cl CONH 2 NO 2 Cl HNO 3 H 2 SO 4 Cl 2 FeCl 3 H 2 CrO 4 SOCl 2 N(Et) 3 2 eq NH 3 Aklomide: used as a veternary antibacterial agent Use the para isomer...
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