The following compound, 2-hydroxycycloheptatrienone, does not give all the usual carbonyl group reactions. (i) Explain this apparent anomaly. Furthermore, explain the significant difference between the relative stability of this compound and its 3- and 4-hydroxy isomers. (ii) What would you expect to be the influence of adding (a) a nitro group as a substituent on the 7-membered ring or (b) an alkyl group, on the degree of aromaticity of the above compound. (iii) Based on your understanding of the hydrogen bonding concept, which isomer would you expect to have a higher m.p, (assuming they are both solids) between 2- and 4- hydroxycycloheptatrienone? Explain your choice.

The following compound, 2-hydroxycycloheptatrienone, does not give all the usual carbonyl group reactions. (i) Explain this apparent anomaly. Furthermore, explain the significant difference between the relative stability of this compound and its 3- and 4-hydroxy isomers. (ii) What would you expect to be the influence of adding (a) a nitro group as a substituent on the 7-membered ring or (b) an alkyl group, on the degree of aromaticity of the above compound. (iii) Based on your understanding of the hydrogen bonding concept, which isomer would you expect to have a higher m.p, (assuming they are both solids) between 2- and 4- hydroxycycloheptatrienone? Explain your choice.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.55P

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