The major product of the reaction is
← JEE Advanced 2015 · Paper 1
ChemistryMultiple correct+4 / -2Question 33 of 60
JEE Advanced 2015 · Paper 1, Chemistry question 33
Answer and worked solution
Official answer: C
Diazotisation. NaNO₂/HCl diazotises the α-amino group.
Neighbouring-group participation. The carboxylate displaces N₂ with inversion, forming an α-lactone. Water then opens it with a second inversion.
Result. Two inversions mean overall retention: 2-hydroxy-4-methylpentanoic acid with the OH in the same position as the original NH₂ (wedge).
(C)