1. Bobby Drake is setting up his reaction and seals the top of his reflux condenser, creating a sealed system, and begins to heat the reaction. Explain the safety issues with Bobbyâs reaction. (10 pts)
2. Methanol is a byproduct of the reaction in this lab. According to Sigma Aldrichâs SDS sheet, what type of gloves should be worn when handling methanol? (10 pts)
3. Scott Summers has obtained an IR spectrum for his product however he must leave to Genosha. Assign the following stretches in the table below for the product. (10 pts)
Figure1: Chemical structure of acetanilide
IR Stretching Frequency (cm-1)
Functional Group/Bond
3057
1662
4. After 10 minutes of drying Warren Worthington notices a severe melting point depression for his benzoic acid sample (80-100 °C) though he should have distilled off all the methanol. He calculates a 115% yield. Offer a reasonable explanation for the observed melting point depression, and unreasonable percent yield. What would you advise Warren to do in order to obtain reasonable data? (20 pts).
5. The hydrolysis of methyl benzoate is performed using a strong base (NaOH) as a catalyst, to form the corresponding carboxylic acid. During Step 11 of this procedure concentrated hydrochloric acid (HCl) is added to obtain the product as a white precipitate. Explain why HCl is added to form the solid. (10 pts)
6. Jean Grey is performing the hydrolysis of methyl benzoate, however after Step 11 she chooses to extract the product out using diethyl ether via liquid/liquid extraction. She realizes that residual methanol will be present in her sample now. What equipment in the lab can she use to remove the methanol, as well as the diethyl ether? What should she add to her flask to ensure she removes the water?(20 pts)
7. In principle it is possible to synthesize methyl benzoate again from the benzoic acid obtained in lab at 100% yield. To do this reaction NaOH and methanol can be used once again, however in order to obtain 100% yield water cannot be present during the reaction. Explain this using the equilibrium expression below. (Hint: It will be helpful to review Le Chatlierâs principle, and use this in your explanation) (25 pts)
Scheme1: Equilbrium of the fisher esterification of benzoic acid to form methyl benzoate.
8. Alex Summers accidentally breaks the container of hydrochloric acid in his fume hood. What are the proper safety protocols that he should follow? (10 pts)
1. Bobby Drake is setting up his reaction and seals the top of his reflux condenser, creating a sealed system, and begins to heat the reaction. Explain the safety issues with Bobbyâs reaction. (10 pts)
2. Methanol is a byproduct of the reaction in this lab. According to Sigma Aldrichâs SDS sheet, what type of gloves should be worn when handling methanol? (10 pts)
3. Scott Summers has obtained an IR spectrum for his product however he must leave to Genosha. Assign the following stretches in the table below for the product. (10 pts)
Figure1: Chemical structure of acetanilide
| IR Stretching Frequency (cm-1) | Functional Group/Bond |
| 3057 | |
| 1662 |
4. After 10 minutes of drying Warren Worthington notices a severe melting point depression for his benzoic acid sample (80-100 °C) though he should have distilled off all the methanol. He calculates a 115% yield. Offer a reasonable explanation for the observed melting point depression, and unreasonable percent yield. What would you advise Warren to do in order to obtain reasonable data? (20 pts).
5. The hydrolysis of methyl benzoate is performed using a strong base (NaOH) as a catalyst, to form the corresponding carboxylic acid. During Step 11 of this procedure concentrated hydrochloric acid (HCl) is added to obtain the product as a white precipitate. Explain why HCl is added to form the solid. (10 pts)
6. Jean Grey is performing the hydrolysis of methyl benzoate, however after Step 11 she chooses to extract the product out using diethyl ether via liquid/liquid extraction. She realizes that residual methanol will be present in her sample now. What equipment in the lab can she use to remove the methanol, as well as the diethyl ether? What should she add to her flask to ensure she removes the water?(20 pts)
7. In principle it is possible to synthesize methyl benzoate again from the benzoic acid obtained in lab at 100% yield. To do this reaction NaOH and methanol can be used once again, however in order to obtain 100% yield water cannot be present during the reaction. Explain this using the equilibrium expression below. (Hint: It will be helpful to review Le Chatlierâs principle, and use this in your explanation) (25 pts)
Scheme1: Equilbrium of the fisher esterification of benzoic acid to form methyl benzoate.
8. Alex Summers accidentally breaks the container of hydrochloric acid in his fume hood. What are the proper safety protocols that he should follow? (10 pts)
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