Cyclopentylamine is treated with HNO ₂ to form compound P. Compound P is oxidized with PCC to form Q. When Q is heated with dilute Ba(OH) ₂ , it forms an intermediate enone R. Finally, R is reacted with one equivalent of CH ₃ MgBr followed by mild acidic workup to yield the final product S. The IUPAC name of the major product S is:

Step-by-step solution

Cyclopentylamine reacts with nitrous acid ( HNO ₂ ) to undergo diazotization followed by hydrolysis, yielding cyclopentanol (P). Cyclopentanol is oxidized by PCC to cyclopentanone (Q). Cyclopentanone undergoes self-aldol condensation upon heating with dilute Ba(OH) ₂ . The initial -hydroxy ketone dehydrates to form the , -unsaturated ketone, 2-cyclopentylidenecyclopentan-1-one (R). Grignard reagents like CH ₃ MgBr typically undergo direct 1,2-addition to the carbonyl carbon of , -unsaturated ketones, rather than 1,