2-Amino-1,1-diphenylethan-1-ol, (C6H5)2C(OH)-CH2NH2, is treated with NaNO2/HCl at 273 K. The main organic product is

1,2-diphenylethan-1-one (deoxybenzoin)

JEE Advanced levelSingle correct optionDifficulty 3 of 3ap086

2-Amino-1,1-diphenylethan-1-ol, $(C X_{6} H X_{5}) X_{2} C (OH) - CH X_{2} NH X_{2}$ , is treated with $NaNO X_{2}$ / $HCl$ at 273 K. The main organic product is

The amine is converted into the diazonium ion

Ph X_{2} C (OH) - CH X_{2} N X_{2} X^{+}

, which loses

N X_{2}

in a semipinacol rearrangement. A phenyl group migrates from the carbinol carbon to the electron-deficient

CH X_{2}

, leaving

PhCH X_{2} - C X^{+} (OH) Ph

, which loses

H X^{+}

to give

PhCH X_{2} - CO - Ph