A) (1 point) Build anthracene, optimize its geometry and examine its structure. Describe its shape. b) (1 point) Measure the C-C bond lengths in anthracene. How do the bond lengths compare to typical C−C or C=C bond distances? c) (1 point) Build N-maleimide, optimize the geometry and examine the structure. Is the molecule flat?

a) The structure of anthracene is planar with all the pi electrons delocalized in the structure to maintain aromaticity.

b) The C-C bond length in anthracene is about 140 pm with all the bond lengths being similar to each other.

The standard C-C bond length is 154 pm while standard C=C bond is about 134 pm. Therefore the bond length in anthracene is smaller than standard C-C bond length and longer than standard C=C bond length. This can be explained from the fact that the C-C bonds in anthracene has be mixed characteristics of single and double bond because of the delocalization of pi electrons over the whole structure. As a result, they are neither fully single nor fully double bond in nature. Hence the observed bond lengths.

c) This molecule is not flat. The N-atom is sp3 hybridized here and the H-atom attached to N will remain out of plane.

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