Conversion of tertiary haloalkane

can someone teach me how do you convert this reactant to get the product?
I consider this as free radical substituition reaction and in the presence of UV , then the H atom in the 2 CH3 will also be substituted.... i want ony the H atom on the carbon bonded to C to be substituted only.

Reply 1

username913907

10

Original post by wilson dang

can someone teach me how do you convert this reactant to get the product?
I consider this as free radical substituition reaction and in the presence of UV , then the H atom in the 2 CH3 will also be substituted.... i want ony the H atom on the carbon bonded to C to be substituted only.

I'll give you a clue to start with, (pretty sure I have an effective synthesis in mind)

The tertiary proton is fairly acidic as the conjugate base is heavily stabilised by the phenyl ring.... start by forming the anion (with a suitable base.... this is important) and then it's one reagent from the product.

Reply 2

wilson dang

OP

7

Original post by JMaydom

I'll give you a clue to start with, (pretty sure I have an effective synthesis in mind)

The tertiary proton is fairly acidic as the conjugate base is heavily stabilised by the phenyl ring.... start by forming the anion (with a suitable base.... this is important) and then it's one reagent from the product.