Which of the following is correct with respect to -I effect of the substituents? (R = alkyl)
- -NH2 < -OR < -F
- -NR2 < -OR < -F
- -NH2 > -OR > -F
- -NR2 > -OR > -F
Answer
(1) -NH2 < -OR < -F, (2) -NR2 < -OR < -F
Solution
The −I (electron-withdrawing inductive) effect increases with the electronegativity of the atom bonded to carbon.
Electronegativity: N < O < F
⇒ −I effect: -NH2 < -OR < -F and also -NR2 < -OR < -F (the attached atom is N in both -NH2 and -NR2).
∴ Both (1) and (2) are correct.
Answer: (1), (2)