Question

3. a. (8 pts) A synthesis of aspirin is shown below. Write a step-by-step, arrow-pushing mechanism for this reaction using only the reagents provided. OH OH +\text{O=C-Cl} pyridine Cl salicylic acid acetyl chloride OH + pyridine-H+ Cl- acetylsalicylic acid (aspirin) c. (5 pts) Explain whether or not the reaction in question 3a is reversible. (If you mixed aspirin, Cl-, and an H+ source, would acetyl chloride and salicylic acid be formed?)

          3.
a. (8 pts) A synthesis of aspirin is shown below. Write a step-by-step, arrow-pushing mechanism
for this reaction using only the reagents provided.
OH
OH
+\text{O=C-Cl}

pyridine

Cl
salicylic acid
acetyl
chloride
OH
+ pyridine-H+ Cl-
acetylsalicylic acid
(aspirin)
c. (5 pts) Explain whether or not the reaction in question 3a is reversible. (If you mixed aspirin,
Cl-, and an H+ source, would acetyl chloride and salicylic acid be formed?)

3.
a. (8 pts) A synthesis of aspirin is shown below. Write a step-by-step, arrow-pushing mechanism
for this reaction using only the reagents provided.
OH
OH
+O=C-Cl

pyridine

Cl
salicylic acid
acetyl
chloride
OH
+ pyridine-H+ Cl-
acetylsalicylic acid
(aspirin)
c. (5 pts) Explain whether or not the reaction in question 3a is reversible. (If you mixed aspirin,
Cl-, and an H+ source, would acetyl chloride and salicylic acid be formed?)

Added by John S.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

Instant Answer

Solved by Expert Chareen Guzman

Step 1

- This leads to the formation of a tetrahedral intermediate, which then collapses, releasing a chloride ion and forming an acylium ion (a positively charged carbon with a double bond to oxygen). Show more…

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A synthesis of aspirin is shown below. Write a step-by-step, arrow-pushing mechanism for this reaction using only the reagents provided. OH OH pyridine OH salicylic acid acetyl chloride acetylsalicylic acid (aspirin) (5 pts) Explain whether or not the reaction in question 3a is reversible. (If you mixed aspirin, CH3COCl, and an H+ source, would acetyl chloride and salicylic acid be formed?) pyridine-H: