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Explain how the following two compounds can have the same
Chapter 18, Problem 18.52(choose chapter or problem)
Explain how the following two compounds can have the same conjugate base. Is this conjugate base aromatic?
Questions & Answers
QUESTION:
Explain how the following two compounds can have the same conjugate base. Is this conjugate base aromatic?
ANSWER:Step 1 of 2
Consider the following two compounds, which can have the same conjugate base.
Note that the most acidic proton in each case is located on the \(s p^{3}\) hybridized ring carbon; vinylic protons are only weakly acidic. Abstraction of a proton from the \(s p^{3}\) ring carbon in either compound leads to an anion that is planar and cyclic. The anion conjugate base has overlapping \(p\) orbitals and a total of \(4 n+2\) ( 6 , in this case) \(\pi\) electrons. This meets the criteria for aromaticity, meaning that the conjugate base in each case is aromatic.