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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Identify the major product of the following reaction sequence:

Options

  1. AProduct (b)
  2. BProduct (c)
  3. CProduct (a)
  4. 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,

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