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Algebra Difficulty 5.3 AIME, harder Find the answer

The skeletal structure of coronene, a hydrocarbon with the chemical formula C24H12\mathrm{C}_{24} \mathrm{H}_{12}, is shown below. Each line segment between two atoms is at least a single bond. However, since each carbon (C) requires exactly four bonds connected to it and each hydrogen (H)(\mathrm{H}) requires exactly one bond, some of the line segments are actually double bonds. How many arrangements of single/double bonds are there such that the above requirements are satisfied?

A number or a short expression. Spacing and $ signs are ignored.

Solution

Note that each carbon needs exactly one double bond. Label the six carbons in the center 1,2,3,4,5,61,2,3,4,5,6 clockwise. We consider how these six carbons are double-bonded. If a carbon in the center is not double-bonded to another carbon in the center, it must double-bond to the corresponding carbon on the outer ring. This will result in the outer ring broken up into (some number of) strings instead of a loop, which means that there will be at most one way to pair off the outer carbons through double-bonds. (In fact, as we will demonstrate later, there will be exactly one way.) Now we consider how many double bonds are on the center ring. - 3 bonds. There are 2 ways to pair of the six carbons, and 2 ways to pair of the outer ring as well, for 4 ways in total. - 2 bonds. Then either two adjacent carbons (6 ways) or two diametrically opposite carbons (3 ways) are not double-bonded, and in the former case the outer ring will be broken up into two "strands" with 2 and 14 carbons each, while in the latter case it will be broken up into two strands both with 8 carbons each, and each produce one valid way of double-bonding, for 9 ways in total. - 1 bond. There are 6 ways to choose the two double-bonded center carbon, and the outer ring will be broken up into four strands with 2,2,2,82,2,2,8 carbons each, which gives one valid way of double-bonding, for 6 ways in total. - 0 bonds. Then the outer ring is broken up into six strands of 2 carbons each, giving 1 way. Therefore, the number of possible arrangements is 4+9+6+1=204+9+6+1=20. Note: each arrangement of single/double bonds is also called a resonance structure of coronene.

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