Give the major product formed by the heating of the following ether with HI.
CH3 | CH3-CH2-CH-CH2-O-CH2-CH3
According to me, the product should be this due to delocalization of positive charge among the neighboring carbon atoms.
CH3 | CH3-CH2-CH-CH2-I + CH3-CH2-OH
I checked the answer in my book and it is completely different:
CH3 | CH3-CH2-CH-CH2-OH + CH3-CH2-I
Now, I think they may have considered steric hindrance to be the deciding factor of site of attack of OH but will not delocalization be dominant over steric effect?
Also, what will be the effect of hyperconjugation on the reaction?