Aromatic compounds which contain non-carbon atoms (e.g., O, N, S) as part of the cyclic conjugated a system are called heteroaromatics. the ring OR a lone pair in a p-orbital. Only one p The heteroatom can be a part of the conjugation as either part of a r bond orbital from the atom can align to contribute to the aromaticity. For example, let's look at furan (shown to the right). How many lone pairs are on the oxygen in this structure? O 3 lone pairs O I lone pair 2 lone pairs O O lone pairs How many electrons are in the r bonds? O 0 electrons O 4 electrons O 2 electrons O 1 electron O 5 electrons O 3 electrons O 6 electrons To determine, the total number of x electrons to use for the Huckel calculation, you need to determine how many of the non-bonding electrons on the oxygen are aligned with the x bonds. Is the red orbital on oxygen aligned with r bonds? O yes O no Is the blue orbital on oxygen aligned with x bonds? O no O yes What is the total number of electrons in the blue orbitals? Based on Huckel calculations, would furan be aromatic? O yes O no

Aromatic compounds which contain non-carbon atoms (e.g., O, N, S) as part of the cyclic conjugated a system are called heteroaromatics. the ring OR a lone pair in a p-orbital. Only one p The heteroatom can be a part of the conjugation as either part of a r bond orbital from the atom can align to contribute to the aromaticity. For example, let's look at furan (shown to the right). How many lone pairs are on the oxygen in this structure? O 3 lone pairs O I lone pair 2 lone pairs O O lone pairs How many electrons are in the r bonds? O 0 electrons O 4 electrons O 2 electrons O 1 electron O 5 electrons O 3 electrons O 6 electrons To determine, the total number of x electrons to use for the Huckel calculation, you need to determine how many of the non-bonding electrons on the oxygen are aligned with the x bonds. Is the red orbital on oxygen aligned with r bonds? O yes O no Is the blue orbital on oxygen aligned with x bonds? O no O yes What is the total number of electrons in the blue orbitals? Based on Huckel calculations, would furan be aromatic? O yes O no

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter18: Aromaticity

Section: Chapter Questions

Problem 7CTQ

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