1. Write the chemical equation for synthesis of salicylic acid from methyl salicylate. (Please draw structures for all organic compounds in this equation. Do not write formula for organic compounds) There are two parts to this equation. The first part is reaction of methyl salicylate with NaOH to form disodium salicylate and the second part is reaction of disodium salicylate with HCl to for salicylic acid ( 2 points)
2. SDS or safety data sheet is a document that provides details about each chemical such as health hazards associated with its use, safety precautions to be taken while handling the chemical and other physical properties of the chemical. Please look up the SDS for methylsalicylate, 6M NaOH and 6M HCl on the internet and list the health hazards associated with the use of these chemicals (3 points)
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3. Convert volume of methyl salicylate used in this synthesis to mass of methyl salicylate (1 point)
4. Complete the following table (3 points)
| Name of chemical |
Mol wt |
No. of gms or ml |
No. of millimoles |
| Methyl salicylate |
? |
? |
? |
| 6M NaOH solution |
? |
? |
? |
| Water |
|
? |
NA |
| 6M HCl |
? |
Add enough to adjust the pH to 2 |
NA |
5. Draw the structures of methyl salicylate and salicylic acid. Circle and identify the functional groups present in both these compounds. Identify the acidic protons in methyl salicylate and salicylic acid (2+2+2 points)
6. In this synthesis, a white precipitate forms immediately upon addition of 6M NaOH to methylsalicylate. What chemical is formed at this step? (Hint: The first reaction to take place is an acid-base reaction)Write a chemical equation for formation of this chemical (2 points)
7. At the end of 30 min of reflux, the white precipitate is no longer present, but has been converted into a product that is fully water soluble. What product is this and write a chemical equation for its formation? (Hint: Ester hydrolysis happens at this stage) (2 points)
8. Calculate the volume of 6M NaOH required to react completely with the amount of methyl salicylate you used. How much of the 6M NaOH that you used was in excess if the theoretical amount? What volume of 6MHCl is needed to neutralize all of the disodium salicylate and the excess NaOH present after the initial reaction? ( 3 points)
9. Calculate the theoretical yield of salicylic acid for this synthesis (2 points)
10. What solvent system was used for recrystallization of salicylic acid? (1 point)
