Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the most suitable reagents for the following transformation:
Options
- AH ₂ NEt and NaOH
- BH ₂ NEt and NaOCH ₃
- CH ₂ NEt and CH ₃ CO ₂ H
- DH ₂ NEt and HCl
Correct answer
C. H ₂ NEt and CH ₃ CO ₂ H
Step-by-step solution
The given transformation is the conversion of a ketone (cyclopentanone) into an imine ( N -ethylcyclopentanimine). This reaction involves the nucleophilic addition of a primary amine, ethylamine ( H₂NEt ), to the carbonyl group, followed by the elimination of a water molecule. The formation of an imine is an acid-catalyzed process. The acid serves two purposes: 1. It protonates the carbonyl oxygen, increasing the electrophilicity of the carbonyl carbon. 2. It protonates the hydroxyl group in the carbinolamine inter