How many sigma/pi bonds are in the aspirin structure?

1 Answer
Truong-Son N.
May 1, 2016

Aspirin is the brand name for acetylsalicylic acid, which is the common name for 2-(acetyloxy)benzoic acid. This compound looks like this:

![https://upload.wikimedia.org/](useruploads.socratic.org)

In a single bond, you have a single sigma bond.

In a double bond, there is one pi bond in addition to the single sigma bond that constituted the single bond.

Thus, if we treat each double bond as a single bond on this structure, we count up the sigma bonds as:

  • 5 "C"-"O" sigma bonds (2 from the carboxylic acid group, and 3 from the acetate group)
  • 2 non-aromatic "C"-"C" sigma bonds (1 from the carboxylic acid group, and 1 on the acetate group)
  • 6 aromatic "C"-"C" sigma bonds (on the benzene ring)

Then, in accounting for the particular bonds that are double bonds, the remaining pi bonds are from:

  • 2 "C"-"O" pi bonds (1 from the carboxylic acid group, and 1 from the acetate group)
  • 3 aromatic "C"-"C" pi bonds (on the benzene ring)

Thus, we have 5 + 2 + 6 = 13 \mathbf(sigma) bonds and 2 + 3 = 5 \mathbf(pi) bonds.

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