Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product of the following reaction sequence:
Options
- AProduct (b)
- BProduct (c)
- CProduct (a)
- DProduct (d)
Correct answer
A. Product (b)
Step-by-step solution
The first step involves a 1,4-conjugate addition of the cyanide ion from NaCN to the , -unsaturated aldehyde, forming a -cyano aldehyde. Ph - CH = CH - CHO NaCN Ph - CH ( CN )- CH ₂- CHO In the second step, the aldehyde reacts with ammonia under mildly acidic conditions to form an imine. Ph - CH ( CN )- CH ₂- CHO NH ₃ / / H ^+ Ph - CH ( CN )- CH ₂- CH = NH The imine then undergoes nucleophilic addition of HCN to form an -amino nitrile. Ph - CH ( CN )- CH ₂- CH = NH HCN Ph - CH ( CN )- CH ₂- CH ( NH ₂)- CN Finally,