Draw in all lone pairs. Circle all the nucleophilic atoms in the following structure. Explain your answer with resonance contributors. The number of lone pairs on the enolate oxygen (O⁻) is :

Question

Draw in all lone pairs. Circle all the nucleophilic atoms in the following structure. Explain your answer with resonance contributors. The number of lone pairs on the enolate oxygen (O − ) is :

TestHub · Accepted Answer

Both oxygen atoms carry lone pairs. The negatively charged oxygen (O^-) has three lone pairs, while the carbonyl oxygen has two. The nucleophilic atoms are the enolate oxygen, the two C=C carbons of the enolate, and the carbonyl oxygen. The resonance contributor shifts the negative charge from one oxygen to the other through the conjugated π system.

Answer: (D).

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