Dolbier HW Solutions 430

Dolbier HW Solutions 430 - the ring. The orientation of the...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Hydrogenation of the double bond of the Diels Alder adduct gives the required product. ( h ) The target molecule is related to the starting material by the retrosynthesis The necessary bromine substituent can be introduced by electrophilic substitution in the acti- vated aromatic ring of m -xylene. The aryl bromide cannot be converted to a carboxylic acid by way of the corresponding nitrile, because aryl bromides are not reactive toward nucleophilic substitution. The Grignard route is necessary. ( i ) The relationship of the target molecule to the starting material requires that there be two synthetic operations: oxidation of the methyl group and nitration of
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: the ring. The orientation of the nitro group requires that nitration must follow oxidation of the p-Chlorotoluene CH 3 Cl 4-Chloro-3-nitrobenzoic acid CO 2 H NO 2 Cl 2,4-Dimethylbenzoic acid 1. Mg, diethyl ether 2. CO 2 3. H 3 O 1 CO 2 H CH 3 CH 3 1-Bromo-2,4-dimethylbenzene Br CH 3 CH 3 m-Xylene Br CH 3 CH 3 1-Bromo-2,4-dimethylbenzene CH 3 CH 3 Br 2 acetic acid (or Br 2 , FeBr 3 ) 2,4-Dimethylbenzoic acid CO 2 H CH 3 CH 3 Br CH 3 CH 3 m-Xylene CH 3 CH 3 H 2 Pt CO 2 H Cl trans-2-Chloro-4-cyclohexenecarboxylic acid CO 2 H Cl trans-2-Chlorocyclo-hexanecarboxylic acid 524 CARBOXYLIC ACIDS __ __ __...
View Full Document

This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

Ask a homework question - tutors are online