Answer the following questions about the structures shown below. a) What is the

Question

Answer the following questions about the structures shown below. a) What is the hybridization of each indicated atom? b) How many pi electrons are in the above molecule? c) Is the fused bicyclic ring system aromatic (A), non-aromatic (NA) or anti-aromatic (AA)? d) Is the mono cyclic ring A, NA or AA? e) Which atom(s) is (are) conjugated with the fused bicyclic ring? f) Which atom(s) is (are) conjugated with the carbonyl group? g) Which nitrogen(s) is (are) strong bases (pKa conjugate acid > 10)? h) Which nitrogen (s) is (are) weak bases (pKa conjugate acid almostequalto 5)? i) Which nitrogen(s) is (are) non basic (pKa conjugate acid

Explanation / Answer

1)

a) atom - hybridisation : 1-sp3 , 4 -sp2 , 10- sp3 , 11- sp2 , 12 -sp , 13- sp2 , 14 - sp3 , 19 - sp2

b) 14 pairs of pi electrons( 8 double bonds + 6 lone pairs from 4 N and one oxygen] = 28 pi electrons

c) aromatic

d) non- aromatic (due to the presence of one sp3 C, no pielectrn ring]

e) 11(extended conjugation after that )

f) 16(extended)

g) 10 [ it is sp3 N , tertiary amine and no resonance]

h) 4 [ sp2 N , lone pair not in resonance]

i) 1 , lone pair on N is in aromatic sextet, 14 due to resonance

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