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

1 Answer
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 sigmaσ bond.

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

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

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

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

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

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