Which of the following is correct with respect to -I effect of the substituents ? (R = alkyl)
1. \(-\)NH\(_2\) < \(-\)OR < \(-\)F
2. \(-\)NH\(_2\) > \(-\)OR > \(-\)F
3. \(-\)NR\(_2\) < \(-\)OR < \(-\)F
4. \(-\)NR\(_2\) > \(-\)OR > \(-\)F
1. \(-\)NH\(_2\) < \(-\)OR < \(-\)F
2. \(-\)NH\(_2\) > \(-\)OR > \(-\)F
3. \(-\)NR\(_2\) < \(-\)OR < \(-\)F
4. \(-\)NR\(_2\) > \(-\)OR > \(-\)F
Best answer
Answer: 3. \(-\)NR\(_2\) < \(-\)OR < \(-\)F
The -I effect increases with the electronegativity of the atom attached to the carbon chain: N < O < F.
Since R = alkyl is specified in the question, the substituents are \(\mathrm{-NR_2,\,-OR,\,-F}\) and the order is \(\mathrm{-NR_2<-OR<-F}\) (option 3).
Note: option 1 (with \(\mathrm{-NH_2}\)) follows the same logic, so the question is slightly ambiguous; the published answer uses the \(\mathrm{-NR_2}\) form.
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