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

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

This note was uploaded on 03/16/2010 for the course CH 53705 taught by Professor Colapret during the Fall '09 term at University of Texas at Austin.

Page1 / 2

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

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online