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Explain how the following two compounds can have the same

Chapter 18, Problem 18.52

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QUESTION:

Explain how the following two compounds can have the same conjugate base. Is this conjugate base aromatic?

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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.

 

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