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1. (6.5 points) The preparation of aspirin is achieved through acetylation of salicylic acid. Provide the full curved-arrow mechanism for this transformation. All starting materials, reagents, and products should be accounted for. ཚེཚེས༔-༩ལིན་ཐིག OH OH salicylic acid H3C + H3C H3PO4 (conc.) CH3 CH3 50 °C to 0 °C H3C OH OH acetic anhydride :O-P-OH : OH HO. acetylsalicylic acid (aspirin) 눈요 CH3 O-P-OH : OH H3C CH3 H3C H. H H3C- acetic acid :: CHEM 238 H3C H3C .0: CH3 HO H но. CH3 H-00 HO Ή OH : OH CH3 HO CH3 CH3 но HO-P―O: I HO: H-O Н H3C- H3C : OH 1

1. (6.5 points) The preparation of aspirin is achieved through acetylation of salicylic acid. Provide the full curved-arrow mechanism for this transformation. All starting materials, reagents, and products should be accounted for. ཚེཚེས༔-༩ལིན་ཐིག OH OH salicylic acid H3C + H3C H3PO4 (conc.) CH3 CH3 50 °C to 0 °C H3C OH OH acetic anhydride :O-P-OH : OH HO. acetylsalicylic acid (aspirin) 눈요 CH3 O-P-OH : OH H3C CH3 H3C H. H H3C- acetic acid :: CHEM 238 H3C H3C .0: CH3 HO H но. CH3 H-00 HO Ή OH : OH CH3 HO CH3 CH3 но HO-P―O: I HO: H-O Н H3C- H3C : OH 1

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.51P
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1. (6.5 points) The preparation of aspirin is achieved through acetylation of salicylic acid. Provide the full curved-arrow mechanism for this transformation. All starting materials, reagents, and products should be accounted for. ཚེཚེས༔-༩ལིན་ཐིག OH OH salicylic acid H3C + H3C H3PO4 (conc.) CH3 CH3 50 °C to 0 °C H3C OH OH acetic anhydride :O-P-OH : OH HO. acetylsalicylic acid (aspirin) 눈요 CH3 O-P-OH : OH H3C CH3 H3C H. H H3C- acetic acid :: CHEM 238 H3C H3C .0: CH3 HO H но. CH3 H-00 HO Ή OH : OH CH3 HO CH3 CH3 но HO-P―O: I HO: H-O Н H3C- H3C : OH 1
Transcribed Image Text:1. (6.5 points) The preparation of aspirin is achieved through acetylation of salicylic acid. Provide the full curved-arrow mechanism for this transformation. All starting materials, reagents, and products should be accounted for. ཚེཚེས༔-༩ལིན་ཐིག OH OH salicylic acid H3C + H3C H3PO4 (conc.) CH3 CH3 50 °C to 0 °C H3C OH OH acetic anhydride :O-P-OH : OH HO. acetylsalicylic acid (aspirin) 눈요 CH3 O-P-OH : OH H3C CH3 H3C H. H H3C- acetic acid :: CHEM 238 H3C H3C .0: CH3 HO H но. CH3 H-00 HO Ή OH : OH CH3 HO CH3 CH3 но HO-P―O: I HO: H-O Н H3C- H3C : OH 1
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