N-acetyl-p-benzoquinone imine (NAPQI) is a toxic metabolite of acetaminophen that can lead to liver damage. The damage results from the addition to liver proteins, which react as a nucleophile with one of the ring carbons. Propose a reasonable mechanism for the following steps that result in the aromatic ring product. HN' Liver Protein H$ Liver Protein OH
N-acetyl-p-benzoquinone imine (NAPQI) is a toxic metabolite of acetaminophen that can lead to liver damage. The damage results from the addition to liver proteins, which react as a nucleophile with one of the ring carbons. Propose a reasonable mechanism for the following steps that result in the aromatic ring product. HN' Liver Protein H$ Liver Protein OH
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 45MP
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![9.35 N-acetyl-p-benzoquinone imine (NAPQI) is a toxic metabolite of acetaminophen that can lead to liver damage. The
damage results from the addition to liver proteins, which react as a nucleophile with one of the ring carbons. Propose
a reasonable mechanism for the following steps that result in the aromatic ring product.
N'
HN
Liver Protein
H$
Liver Protein
ОН](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F29702385-953d-4f81-a91e-17e99ae97064%2F91b4c041-2cdf-424b-bb7c-c9c290b8bee3%2Frkjfhxm_processed.jpeg&w=3840&q=75)
Transcribed Image Text:9.35 N-acetyl-p-benzoquinone imine (NAPQI) is a toxic metabolite of acetaminophen that can lead to liver damage. The
damage results from the addition to liver proteins, which react as a nucleophile with one of the ring carbons. Propose
a reasonable mechanism for the following steps that result in the aromatic ring product.
N'
HN
Liver Protein
H$
Liver Protein
ОН
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