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Passage the Drug Paracetamol, Also Known as Acetaminophen, Is Used to to Relieve

Question 89

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Passage
The drug paracetamol, also known as acetaminophen, is used to relieve pain and fever, and is a metabolite of the antipyretic drug phenacetin (Figure 1) .  These two drugs have similar medicinal properties, but phenacetin has been shown to be carcinogenic and cause kidney damage.  Acetaminophen is a safer alternative to phenacetin when taken in therapeutic doses.
Passage The drug paracetamol, also known as acetaminophen, is used to relieve pain and fever, and is a metabolite of the antipyretic drug phenacetin (Figure 1) .  These two drugs have similar medicinal properties, but phenacetin has been shown to be carcinogenic and cause kidney damage.  Acetaminophen is a safer alternative to phenacetin when taken in therapeutic doses. <strong>Figure 1</strong>  Structure of phenacetinA student synthesizes acetaminophen in a laboratory from phenol according to the reactions shown.  The synthesis begins with the nitration of phenol by sodium nitrate (NaNO<sub>3</sub>) to produce the mixture of the isomers 2-nitrophenol and 4-nitrophenol (Reaction 1) .  These isomers can be easily separated by steam distillation to isolate the desired product, 4-nitrophenol.  Reduction of the nitro group with sodium borohydride (NaBH<sub>4</sub>) (Reaction 2) is followed by acetylation of the amine with acetic anhydride (Reaction 3) to afford the final product, acetaminophen. <strong>Reaction 1</strong> <strong>Reaction 2</strong> <strong>Reaction 3</strong> -Based on the structure of acetaminophen shown in the passage, in which region of the infrared spectrum will it most likely show a strong absorption? A) 1690-1650 cm<sup>−1</sup> B) 2150-2100 cm<sup>−1</sup> C) 2260-2240 cm<sup>−1</sup> D) 2850-2750 cm<sup>−1</sup> Figure 1  Structure of phenacetinA student synthesizes acetaminophen in a laboratory from phenol according to the reactions shown.  The synthesis begins with the nitration of phenol by sodium nitrate (NaNO3) to produce the mixture of the isomers 2-nitrophenol and 4-nitrophenol (Reaction 1) .  These isomers can be easily separated by steam distillation to isolate the desired product, 4-nitrophenol.  Reduction of the nitro group with sodium borohydride (NaBH4) (Reaction 2) is followed by acetylation of the amine with acetic anhydride (Reaction 3) to afford the final product, acetaminophen.
Passage The drug paracetamol, also known as acetaminophen, is used to relieve pain and fever, and is a metabolite of the antipyretic drug phenacetin (Figure 1) .  These two drugs have similar medicinal properties, but phenacetin has been shown to be carcinogenic and cause kidney damage.  Acetaminophen is a safer alternative to phenacetin when taken in therapeutic doses. <strong>Figure 1</strong>  Structure of phenacetinA student synthesizes acetaminophen in a laboratory from phenol according to the reactions shown.  The synthesis begins with the nitration of phenol by sodium nitrate (NaNO<sub>3</sub>) to produce the mixture of the isomers 2-nitrophenol and 4-nitrophenol (Reaction 1) .  These isomers can be easily separated by steam distillation to isolate the desired product, 4-nitrophenol.  Reduction of the nitro group with sodium borohydride (NaBH<sub>4</sub>) (Reaction 2) is followed by acetylation of the amine with acetic anhydride (Reaction 3) to afford the final product, acetaminophen. <strong>Reaction 1</strong> <strong>Reaction 2</strong> <strong>Reaction 3</strong> -Based on the structure of acetaminophen shown in the passage, in which region of the infrared spectrum will it most likely show a strong absorption? A) 1690-1650 cm<sup>−1</sup> B) 2150-2100 cm<sup>−1</sup> C) 2260-2240 cm<sup>−1</sup> D) 2850-2750 cm<sup>−1</sup> Reaction 1
Passage The drug paracetamol, also known as acetaminophen, is used to relieve pain and fever, and is a metabolite of the antipyretic drug phenacetin (Figure 1) .  These two drugs have similar medicinal properties, but phenacetin has been shown to be carcinogenic and cause kidney damage.  Acetaminophen is a safer alternative to phenacetin when taken in therapeutic doses. <strong>Figure 1</strong>  Structure of phenacetinA student synthesizes acetaminophen in a laboratory from phenol according to the reactions shown.  The synthesis begins with the nitration of phenol by sodium nitrate (NaNO<sub>3</sub>) to produce the mixture of the isomers 2-nitrophenol and 4-nitrophenol (Reaction 1) .  These isomers can be easily separated by steam distillation to isolate the desired product, 4-nitrophenol.  Reduction of the nitro group with sodium borohydride (NaBH<sub>4</sub>) (Reaction 2) is followed by acetylation of the amine with acetic anhydride (Reaction 3) to afford the final product, acetaminophen. <strong>Reaction 1</strong> <strong>Reaction 2</strong> <strong>Reaction 3</strong> -Based on the structure of acetaminophen shown in the passage, in which region of the infrared spectrum will it most likely show a strong absorption? A) 1690-1650 cm<sup>−1</sup> B) 2150-2100 cm<sup>−1</sup> C) 2260-2240 cm<sup>−1</sup> D) 2850-2750 cm<sup>−1</sup> Reaction 2
Passage The drug paracetamol, also known as acetaminophen, is used to relieve pain and fever, and is a metabolite of the antipyretic drug phenacetin (Figure 1) .  These two drugs have similar medicinal properties, but phenacetin has been shown to be carcinogenic and cause kidney damage.  Acetaminophen is a safer alternative to phenacetin when taken in therapeutic doses. <strong>Figure 1</strong>  Structure of phenacetinA student synthesizes acetaminophen in a laboratory from phenol according to the reactions shown.  The synthesis begins with the nitration of phenol by sodium nitrate (NaNO<sub>3</sub>) to produce the mixture of the isomers 2-nitrophenol and 4-nitrophenol (Reaction 1) .  These isomers can be easily separated by steam distillation to isolate the desired product, 4-nitrophenol.  Reduction of the nitro group with sodium borohydride (NaBH<sub>4</sub>) (Reaction 2) is followed by acetylation of the amine with acetic anhydride (Reaction 3) to afford the final product, acetaminophen. <strong>Reaction 1</strong> <strong>Reaction 2</strong> <strong>Reaction 3</strong> -Based on the structure of acetaminophen shown in the passage, in which region of the infrared spectrum will it most likely show a strong absorption? A) 1690-1650 cm<sup>−1</sup> B) 2150-2100 cm<sup>−1</sup> C) 2260-2240 cm<sup>−1</sup> D) 2850-2750 cm<sup>−1</sup> Reaction 3
-Based on the structure of acetaminophen shown in the passage, in which region of the infrared spectrum will it most likely show a strong absorption?


A) 1690-1650 cm−1
B) 2150-2100 cm−1
C) 2260-2240 cm−1
D) 2850-2750 cm−1

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