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From the two compounds below identify which would produce the more acidic conjugate acid along with ...

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From the two compounds below identify which would produce the more acidic conjugate acid along with ...

From the two compounds below identify which would produce the more acidic conjugate acid along with the best explanation.

▸ The conjugate acid of I is more acidic due to protonation of the localized electrons on the nitrogen atom.

▸ The conjugate acid of I is more acidic as compound II has resonance in the aromatic ring.

▸ The conjugate acid of II is more acidic as it would have three hydrogen atoms attached.

▸ Once both compounds are protonated they can no longer hydrogen bond and thus are of equal acidity.

▸ The conjugate acid of II is more acidic as the compound would no longer have delocalized electrons.

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Organic Chemistry

Edition: 4^th

Author: Klein

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