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Dolbier HW Solutions 432 - 526 CARBOXYLIC ACIDS(b As in...

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( b ) As in part ( a ), lactone formation is possible only when the hydroxyl and carboxyl groups are cis. Although the most stable conformation of cis -3-hydroxycyclohexanecarboxylic acid has both substituents equatorial and is unable to close to a lactone, the diaxial orientation is accessible and is capable of lactone formation. Neither conformation of trans -3-hydroxycyclohexanecarboxylic acid has the substituents close enough to each other to form an unstrained lactone. 19.25 ( a ) The most stable conformation of formic acid is the one that has both hydrogens anti. A plausible explanation is that the syn conformation is destabilized by lone-pair repulsions. ( b ) A dipole moment of zero can mean that the molecule has a center of symmetry. One structure
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