3–Amino–2,3–dimethyl butan–2–ol when treated with NaN O 2 / HCl gives product (X). (X) on treatment with LiAl H 4 forms (Y). (Y) on heating with conc. H 2 S O 4 forms (Z). If α-H of Z is (P) t

Question

3–Amino–2,3–dimethyl butan–2–ol when treated with NaN O 2 ​ / HCl gives product (X). (X) on treatment with LiAl H 4 ​ forms (Y). (Y) on heating with conc. H 2 ​ S O 4 ​ forms (Z). If α-H of Z is (P) than find (P–3).

TestHub · Accepted Answer

Nitrous deamination plus methyl migration gives pinacolone by semipinacol rearrangement. LiAlH₄ gives 3,3-dimethylbutan-2-ol. Acid dehydration/rearrangement gives 2,3-dimethylbut-2-ene. Its four methyl groups contain twelve allylic α-H, so P-3=12-3=9.

Source solution:

Chemistry - AMINES Question with Solution | TestHub

Doubts & Discussion