These Compounds Have Very Different Acidities

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The Answer is Each of the compounds contains an allylic proton. The allylic protons in compound A are double allylic since it is next to two double bonds. The resulting carbanion can be delocalized to give a stable carbanion.

Each of the compounds contains an allylic proton. The allylic protons in compound A are double allylic since it is next to two double bonds. The resulting carbanion can be delocalized to give a stable carbanion. Compound B contains two equivalent allylic protons. There are only two resonance structures possible. Compound C also contains a doubly allylic proton. In addition, the resulting carbanion results in an aromatic ring, which is very stable. The charge can be delocalized to each carbon in the ring. The most acidic compounds will have the most stable conjugate base. Thus, compound C is the most acidic, followed by compound A, then compound B.

Compound B contains two equivalent allylic protons. There are only two resonance structures possible.

Compound C also contains a doubly allylic proton. In addition, the resulting carbanion results in an aromatic ring, which is very stable. The charge can be delocalized to each carbon in the ring.

The most acidic compounds will have the most stable conjugate base. Thus, compound C is the most acidic, followed by compound A, then compound B.

These Compounds Have Very Different Acidities

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These Compounds Have Very Different Acidities

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