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

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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
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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 __ __ __...
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