Question

4-pyranone will readily undergo an acid-base reaction. Identify the reaction conditions that will result in the formation of an aromatic product. Then, draw the aromatic resonance product structure. Include all lone pairs in your structure. Ignore inorganic byproducts.

Answer 1

To form an aromatic product from 4-pyranone, strong base and aprotic solvent should be used. The conjugate base formed through deprotonation of 4-pyranone is resonance stabilized and aromatic.

Step-by-step explanation:

When 4-pyranone undergoes an acid-base reaction, the conditions that result in the formation of an aromatic product are the use of a strong base and aprotic solvent. A strong base, such as sodium hydroxide (NaOH), can deprotonate the 4-pyranone molecule to form its conjugate base, which is resonance stabilized and aromatic. An example of the aromatic resonance product structure is shown below: