In the synthesis of salicylic acid from wintergreen

In the synthesis of salicylic acid from wintergreen oil, what is the source of the nucleophile (What attacks the ester group in wintergreen
oil)?
Sulfuric acid B. Sodium hydroxide C. Methyl salicylate D. Salicylic acid E. Disodium salicylate
2. Choose all statements which are true regarding the safety issues for 6.0M Sodium Hydroxide solution?
A. Repeated eye exposure may cause corneal erosion or loss of vision.
B. Strongly corrosive to body tissue and moderately toxic by ingestion.
C. In case of exposure flush exposed area with excess water for 15 minutes
3. Your percent yield in the synthesis of salicylic acid was lower than expected. Which of the following is NOT a good reason for the low yield?
A. NaOH was added in excess to methyl salicylate.
B. High temperature evaporated the product .
C. After adding acid during workup the pH was 5.
D. The product had not dissolved before starting recrystallization.
E. You did not use enough methyl salicylate.
4. What is true regarding the safety issues for 3.0 M Sulfuric acid solution?
A. May severely irritate mucous membranes and respiratory tract.
B. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
C. Causes severe burns and eye damage upon direct contact.
5. Complete the following statements. (3 point)- You can write the letter corresponding to the correct choice from the table of reagents below
1. In Lab 4 this week, _____ B ___ attacks Methyl salicylate.
2. _____ E _____ is acidified to yield the final product.
3. ______ A ____ causes severe burns and eye damage upon direct contact.
A. 3 M Sulfuric acid B. 6 M Sodium hydroxide C. Methyl salicylate D. Salicylic acid E. Disodium salicylate
F. Oil of wintergreen G. Sodium sulfate
6. In Synthesis of salicylic acid from wintergreen oil, if you started with 0.025 Moles of methyl salicylate (mw=152.1) and recovered 2.87 g of
product, calculate the percent yield of salicylic acid (mw=138.1)? SHOW YOUR WORK
0.025 Moles of methyl salicylate = 25 mmoles = 25 x 138.1 = 3.45 g
theoretical yield of Salicylic acid. = 3.45 g
% yield = 2.87/3.45 x 100 = 83.2 %
1 M NaOH solution
excess
3 M H
2
SO
4
solution
OH
O O
ONa
NaO O
OH
HO O

Lab 7: Preparation of 2-chloro-2-methylbutane–An S
N
1 Reaction
Structures : 2-methyl-2-butanol; t-amyl alcohol; t-pentyl alcohol? 2-chloro-2-methyl butane ; t-amyl chloride; t-pentyl chloride ?
Definations: an oxonium ion; carbocation; S
N
1 reaction; S
N
2 reaction; bimolecular transition state
Reaction and Mechanism:
a. Mechanism of reaction of tertiary alcohol with HCl /HBr ?
b. Mechanism of reaction of Primary alcohol with HCl /HBr ?
c. Chemical reactions of primary or tertiary Alkyl Halide with silver nitrate?
d. Chemical reactions of primary or tertiary Alkyl Halide with sodium iodide?
Think about
a. Why did we use sodium bicarbonate can you use NaOH ?
b. Why did we use silver nitrate test can you use sodium iodide test ? Will it work for tertiary halides , why not ?
c. What are possible side products in this reaction, what could be the mechanism?