Dolbier HW Solutions 431

Dolbier HW Solutions 431 - 525 CARBOXYLIC ACIDS methyl...

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methyl group of the starting material Nitration of p -chlorobenzoic acid gives the desired product, because the directing effects of the chlorine (ortho, para) and the carboxyl (meta) groups reinforce each other. ( j ) The desired synthetic route becomes apparent when it is recognized that the Z alkene stereoisomer may be obtained from an alkyne, which, in turn, is available by carboxylation of the anion derived from the starting material. The desired reaction sequence is Hydrogenation of the carbon carbon triple bond of 2-butynoic acid over the Lindlar catalyst converts this compound to the Z isomer of 2-butenoic acid. 19.24 ( a ) Only the cis stereoisomer of 4-hydroxycyclohexanecarboxylic acid is capable of forming a lactone, as can be seen in the following drawings or with a molecular model. The most stable
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