Q. 1-1-32E - Organic Chemistry (Mcmurry)

Question

Oxaloacetic acid, an important intermediate in food metabolism, has the formula and contains three  bonds and two  bonds. Propose two possible structures.

Step-by-Step Solution

Answer

                           Two possible structures of oxaloacetic acid

Oxaloacetic acid

The molecular formula of oxaloacetic acid is .The structure of oxaloacetic aid is represented as follows:

Oxaloacetic acid

Oxaloacetic acid , has three bonds and two bonds

Possibilities

As given oxaloacetic acid should have three C=O bonds and two O-H bonds these can be drawn by keeping one OH group in the last carbon and one in the second carbon where there is no C=O bond.

Trial and error method

By using the trial and error method to determine how the atoms of can be arranged together. Two possible structures of with three  bonds and two bonds are shown:

                                  Two possible structures of oxaloacetic acid