Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product formed in the following reaction:
Correct answer
0
Step-by-step solution
The given reactant is 3,3-dimethyl-2-oxobutanal, which contains both a ketone and an aldehyde group but no -hydrogen atoms. When treated with concentrated NaOH, it undergoes an intramolecular Cannizzaro reaction. The mechanism proceeds as follows: 1. The hydroxide ion ( OH^- ) acts as a nucleophile and attacks the more electrophilic and less sterically hindered carbonyl carbon, which is the aldehyde carbon, forming a tetrahedral intermediate: (CH₃)₃C-CO-CH(OH)(O^-) . 2. A hydride ion ( H^- ) shifts from this interm