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Shown below is the reaction mechanism of the acetylation of salicylic acid with acetic anhydride in the presence of phosphoric acid to produce aspirin. st i H COOH O H COOH 9/ H-A COOH он COOH COOH COOH

Shown below is the reaction mechanism of the acetylation of salicylic acid with acetic anhydride in the presence of phosphoric acid to produce aspirin. st i H COOH O H COOH 9/ H-A COOH он COOH COOH COOH

Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.44P
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Shown below is the reaction mechanism of the acetylation of salicylic acid with acetic anhydride in the presence of phosphoric acid to produce aspirin. COOH OH COOH & C H-A LA Which statement below best describes step 5 of the reaction mechanism? 3 COOH Hoto. AH O COOH ROH 5. HO COOH Jak to Co HO COOH O An oxygen on one of the carbonyl groups takes a proton from phosphoric acid activating the carbonyl group toward nucleophilic substitution giving rise to resonance forms. O The nucleophilic alcohol oxygen attacks the now electrophilic carbon on the carbonyl, breaking the double bond and forming a tetrahedral intermediate. ● Deprotonation of the positively charged oxygen atom to the conjugate base of phosphoric acid. O To become a better leaving group the oxygen atom takes a proton from phosphoric acid. O The double bond re-forms with the neutral oxygen in the OH group. Because carbon does not want to have five bonds, electron transfer to the positively charged oxygen results in the group leaving as acetic acid. O Now that the double bond has re-formed the positively charged oxygen is deprotonated by the conjugate base of phosphoric acid. Clear my choice
Transcribed Image Text:Shown below is the reaction mechanism of the acetylation of salicylic acid with acetic anhydride in the presence of phosphoric acid to produce aspirin. COOH OH COOH & C H-A LA Which statement below best describes step 5 of the reaction mechanism? 3 COOH Hoto. AH O COOH ROH 5. HO COOH Jak to Co HO COOH O An oxygen on one of the carbonyl groups takes a proton from phosphoric acid activating the carbonyl group toward nucleophilic substitution giving rise to resonance forms. O The nucleophilic alcohol oxygen attacks the now electrophilic carbon on the carbonyl, breaking the double bond and forming a tetrahedral intermediate. ● Deprotonation of the positively charged oxygen atom to the conjugate base of phosphoric acid. O To become a better leaving group the oxygen atom takes a proton from phosphoric acid. O The double bond re-forms with the neutral oxygen in the OH group. Because carbon does not want to have five bonds, electron transfer to the positively charged oxygen results in the group leaving as acetic acid. O Now that the double bond has re-formed the positively charged oxygen is deprotonated by the conjugate base of phosphoric acid. Clear my choice
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