Which of the following compounds will yield ortho substitute

Which of the following compounds will yield ortho substituted compound as the major product for nitation reaction? Select one: a. toluene Ob. ethylbenzene c. cumene O d. t-butylbenzene e. none of these Next page

Solution

(A). Toluene. This is because unlike t-butyl there is less steric hindrance. Also methyl is very small functional group, thus it requires less stabilisation than ethyl group in para position. Also there are two ortho groups which are equally probable. But only one para group. Thus though it is both ortho and para director, major product is ortho