Major product of the following reaction is [figure]
- [figure]
- [figure]
- [figure]
- [figure]
Answer
(2) [figure]
Solution
Excess CH3MgBr attacks both groups.
Nitrile: one CH3MgBr adds to C≡N giving an imine salt, which H3O+ hydrolyses to a methyl ketone:
Ar-C N CH3MgBr Ar- NMgBr \|C-CH3 H3O+ Ar- O \|C-CH3
Ester: the ketone first formed reacts with a second CH3MgBr, so the ester ends up as a 3° alcohol:
Ar-CO2CH3 2 CH3MgBr Ar-C(CH3)2-OMgBr
H3O+ Ar-C(CH3)2-OH
[figure]
Hence the product carries –COCH3 and –C(CH3)2OH in para positions.
Answer: (2)