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Question
Arrange the given compounds in decreasing order of their basicity.
Arrange the given compounds in decreasing order of their basicity.
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Solution
The correct option is A (i) > (ii) > (iii)
Comparing the three structures, we can see that there is no bulky group at ortho position of compound (i). This make the conjugate acid of (i) more stable and hence has the highest basic strength.
Group at ortho position of (iii) is more bulkier than (ii). Thus on formation of conjugate acid, (iii) will feel more steric hindrance and this effect will destabilise the conjugate acid making it less basic than (ii). This effect is called steric inhibition of protonation.
So the order of basic strength is
(i) > (ii) > (iii)
Comparing the three structures, we can see that there is no bulky group at ortho position of compound (i). This make the conjugate acid of (i) more stable and hence has the highest basic strength.
Group at ortho position of (iii) is more bulkier than (ii). Thus on formation of conjugate acid, (iii) will feel more steric hindrance and this effect will destabilise the conjugate acid making it less basic than (ii). This effect is called steric inhibition of protonation.
So the order of basic strength is
(i) > (ii) > (iii)
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