Organic Chemistry

SOLUTION E4.3

Although structure 1 has a Huckel number of p-electrons is it not planar. The hydrogens attached to the middle carbons bump into each other, pushing the molecule out of a plane making the molecule non-aromatic. Structure 2 is kept planar owing to the carbon bridge that replaces the hydrogens. As a result it is planar and it is aromatic.
 

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