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Dolbier HW Solutions 436 - 530 CARBOXYLIC ACIDS The...

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The critical signal in maleic acid is that of the vinyl protons, which normally is found in the range 5 7 ppm. Maleic acid is compound B. Compound A is malonic acid. Here we have a methylene group bearing two carbonyl substituents. These methylene protons are more shielded than the aldehyde proton of formic acid or the vinyl pro- tons of maleic acid. 19.33 Compounds A and B both exhibit 1 H NMR absorptions in the region 11 12 ppm characteristic of carboxylic acids. The formula C 4 H 8 O 3 suggests an index of hydrogen de fi ciency of 1, accounted for by the carbonyl of the carboxyl group. Compound A has the triplet quartet splitting indicative of an ethyl group, and compound B has two triplets, suggesting CH 2 CH 2 . 19.34 ( a ) The formula of compound A (C 3 H 5 ClO 2 ) has an index of hydrogen de fi ciency of 1 the carboxyl group. Only two structures are possible: Compound A is determined to be 3-chloropropanoic acid on the basis of its 1 H NMR spec-
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