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Organic Chemistry
Found in: Page 78

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Short Answer

Which anion (A or B) is the stronger base?

B is the stronger base.

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Step by Step Solution

Determination of strong organic bases

In organic chemistry, strong bases are determined based on the free lone pair of electrons.

If the adjacent lone pair of electrons does not undergo delocalization, the compound is a strong base.

Effect of lone pairs on basicity

In compound A, the oxide ion containing the lone pair of electrons shifts towards the electron-deficient carbonyl carbon (C=O). Due to this, the delocalization of lone pair of electrons on an oxygen atom occurs. Hence, A is not a strong base.

Conjugation of an oxide ion

In compound B, the oxide ion-containing lone pair of electrons are free to donate. Its electron-donating tendency is further enhanced by the cyclohexyl group. Hence, B is a strong base.

Therefore, B is a stronger base than A.

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