Pair Red Blue
organic chemistry help!!! URGENT?
Below is a molecule that possesses 2 aromatic rings fused together.
http://www.webassign.net/userimages/kasandbe@ncsu/CH221_ssii_02/aromatic.gif
a) Select the nitrogen(s) that possess a "true" lone pair.
( red , blue, orange, yellow or purple ?)
b) Select the nitrogen that has the most basic lone pair.
c) Select the nitrogen that has the least basic "lone pair".
thanks for your help!!!
a) Assuming the definition of 'true' lone pair means one that does not contribute to aromaticity (like the purple one does) and does not have a resonance with the aromatic system (like the red one does) then the answer is the orange, blue and yellow ones. These lone pairs are orthogonal to the pi-system and act as lone pairs.
If the definition of 'true' lone pair means one that is in an sp3 orbital, then the answer is the red one.
Basicity - pKa values of conjugate acids:
red: anilinic nitrogens are around 3-4
blue: pyridine nitrogens are around 5
yellow: pyridine nitrogens are around 5
orange: imidazole nitrogens are around 7
purple: delocalised lone pair nitrogens are around -4
Therefore:
b) most basic is orange
c) least basic is purple
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