CHMB41 Organic Chemistry Midterm 1 Testbank

1) Classify the following structures as aromatic (A), anti-aromatic (AA) or non-aromatic
(NA). (4 points)




2) Identify the hybridization of all heteroatoms (O, N) in the structure below using the legend
provided. (3 points)




3) Highlight/circle all atoms and bonds in the structure below which are part of a conjugated
system. Indicate the total number of electron pairs that can be classified as conjugated. (3
points)


Number of conjugated electron pairs: ____7_____




4) The following structures are not aromatic because they fail to meet one or more of the four
criteria required for aromaticity. Next to each structure, briefly state the reason(s) why it
cannot be classified as aromatic. (3 points)

Structure Explanation (why is it NOT aromatic)

Has 8 pi electrons (does not follow Huckel’s rule, 4n+2)


Not all atoms have a p orbital (N is sp3 hybridized)


Not cyclic


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, 5) Circle the most likely mechanism for the following reactions. (3 points)




6) Assign the appropriate reaction coordinate diagram/energy diagram to each of the
reactions below (circle the correct letter). (4 points)




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