Question

Hello,

5) (10 points) a) How would you convert the following molecule to an aromatic structure? Show any reagents and the aromatic product you would obtain, and explain why the product is aromatic сн. aromatic structure b) is the starting material aromatic, antiaromatic or nonaromatic? Why?

I know how to determine if a structure is aromatic or anti or no aromatic but I do not know how to convert another molecule into an aromatic structure. Please show how to convert this molecule into an aromatic structure? Show the reagents and steps used to do so and explain why it is an aromatic product.

Thank you So much!

Answer 1

Given comound is non aromatic because there is presence of one sp3 hybridized carbon and this is unconjugated system,

this compound will be aromatic if that sp3 hybridized carbon converted to carbanion whose negative charge delocalized over all double bonds and make this system aromatic 10 pi electron system by using NaOH, proton on SP3 hybridized carbon is abstraced and anion is formed
H Hн

I H H NaOH Non aromatic 8 pi electrons Aromatic electrons 10 pi