Dolbier HW Solutions 269

Dolbier HW Solutions 269 - 263 ARENES AND AROMATICITY(d...

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( d ) There are only three tetra f uorobenzenes. The two hydrogens may be ortho, meta, or para to each other. ( e ) There are only two naphthalenecarboxylic acids. ( f ) There are three isomeric bromoanthracenes. All other positions are equivalent to one of these. 11.26 There are three isomeric trimethylbenzenes: Their relative stabilities are determined by steric effects. Mesitylene (the 1,3,5-trisubstituted iso- mer) is the most stable because none of its methyl groups are ortho to any other methyl group. Ortho substituents on a benzene ring, depending on their size, experience van der Waals strain in the same way that cis substituents on a carbon carbon double bond do. Because the carbon carbon bond length in benzene is somewhat longer than in an alkene, these effects are smaller in magni- tude, however. The 1,2,4-substitution pattern has one methyl
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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