Emily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared. 1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed? aniline aqueous ethanol water acetic acid 2. According to PubChem, acetanilide melts at 114°C. Emily measured a melting point of 96 - 104°C for the solid they collected. What can be said about this solid? - Melting point does not indicate whether a sample is pure or not - The experimental range is narrow and close to the literature value, suggesting it is not completely pure - The experimental range is narrow and close to the literature value, suggesting it is completely pure - The experimental range is wide and lower than the literature value, suggesting it is not completely pure 3. What is the total pressure of this system at 179°C? Temperature Pressure of 1,2-propanediol  Pressure of sulfolane 179°C 0.757 atm 0.0578 atm 4. Normal atmospheric pressure is 1.0 atm. Is this mixture boiling at 179C at normal pressure? - yes -no  - not enough info

EBK A SMALL SCALE APPROACH TO ORGANIC L
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Chapter20: Nucleophilic Substitution Reactions: Competing Nucleophiles
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Emily synthesized acetanilide by stirring aniline and acetic anhydride together in water at 100C. Acetanilide is a solid at room temperature, while everything else is a liquid. Emily noted that while the reaction was running, everything was dissolved and the liquid was a pale orange. Emily allowed the reaction to cool to room temperature and then cooled it in an ice bath. After the slow cooling, a solid appeared.

1. Based only on Emily's observations from this procedure, what solvent does she know will work to recrystallize the acetanilide if needed?

aniline

aqueous ethanol

water

acetic acid

2. According to PubChem, acetanilide melts at 114°C. Emily measured a melting point of 96 - 104°C for the solid they collected. What can be said about this solid?

- Melting point does not indicate whether a sample is pure or not

- The experimental range is narrow and close to the literature value, suggesting it is not completely pure

- The experimental range is narrow and close to the literature value, suggesting it is completely pure

- The experimental range is wide and lower than the literature value, suggesting it is not completely pure

3. What is the total pressure of this system at 179°C?

Temperature Pressure of 1,2-propanediol  Pressure of sulfolane
179°C 0.757 atm 0.0578 atm

4. Normal atmospheric pressure is 1.0 atm. Is this mixture boiling at 179C at normal pressure?

- yes
-no 
- not enough info
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