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Question 45

What is the major product "P" of the following reaction?

In the general aliphatic reaction, when a primary aliphatic amine ($$R-NH_2$$) is treated with nitrous acid ($$HNO_2$$)—which is generated in situ by mixing sodium nitrite ($$NaNO_2$$) and hydrochloric acid ($$HCl$$)—it rapidly undergoes diazotization to form an aliphatic diazonium salt intermediate ($$[R-N_2^+Cl^-]$$). Unlike aromatic diazonium salts, these aliphatic diazonium salts are highly unstable even at very low temperatures. Nitrogen gas is an excellent leaving group and immediately departs, allowing the resulting carbocation to be instantly attacked by water ($$H_2O$$) from the aqueous solvent. This transformation is represented by the general equation:

$$R-NH_2 \xrightarrow{NaNO_2 + HCl} [R-N_2^+Cl^-] \xrightarrow{H_2O} R-OH + N_2 \uparrow + HCl$$

Consequently, as shown in the final step of the reaction sequence, the major compound formed is an aliphatic alcohol ($$R-OH$$), accompanied by the brisk effervescence of nitrogen gas ($$N_2$$). Therefore, this corresponds to Option D.

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