The ease of nitration and the distribution of ortho, meta, and para isomers is d

Question

The ease of nitration and the distribution of ortho, meta, and para isomers is determined by the nature of the substituent(s) on the aromatic ring. In general, substituents are divided into three broad categories: 1) activating and o-lp- directing; 2) deactivating and o-p- directing; and 3) deactivating and m- directing. Table 19.1, page 932 of Bruice lists the most common substituents and their effects on the reactivity of electrophilic aromatic substitution. Using this table, predict the effect the substituent-COOCH3 will have in your reaction and write your prediction below. What effect will this substituent have on the reactivity and orientation of nitration? CH3

Explanation / Answer

If an aromatic ring has -COOCH3 as a substituent and the ring is subjected to Nitration, the result will be a meta-substituting product. This is because -COOCH3 is electron withdrawing (relative to Hydrogen)and does not donate electrons by a resonance effect, thus decreasing the reactivity of the aromatic ring specially at ortho and para positions.

Thus -COOCH3 is a deactivating and m-directing group

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