Question

11. The TLC shown below was taken in step 4 of the procedure for reaction 3: 00 3 SM=0,m,p-methylaniline Co= Co-Spot RM= Reaction Mixture 00 SM CO RM a) Which spot is likely the para isomer of methylaniline? How could you tell? (2 points) b) Which spot is likely the acetylated para product (p-methylacetanilide)? How can you tell? (2 points) c) Keeping in mind we are only trying to acetylate the para isomer of methylaniline, is the reaction complete? (1 point)

Procedure for Virtual Lab 3: Dehydration of an alcohol and GC analysisDehydration of 2-methylcyclohexanol

1. Observe the equipment and chemicals that will be used for the reaction.2. The aluminum block is placed on thehot plate and 2-3 boiling chips are added to a conical vial. 3. The vial is placed into one of the openings on the aluminum block. 4. 1mL of 2-methylcyclohexanol is added to the conical vial. 5. 2mL of 85% phosphoric acid is added to the conical vial. 6. A Hickman still head is attached to the conical vial and the screw cap that serves as the junction is lightly tightened. 7. The still head is securedwith a clamp.8. A thermometer is suspended with aclamp so that the tip is about 1cm above the liquid level to measure the temperature of the vapor rather than the liquid.9. The reaction is heated to boilingand the temperature of the still head is monitored as distillate is collected. The heat is adjusted to keep the temperature of the vapor below 95°C and the distillation pot is not allowed to run dry.10. Observe as the Hickman condenserfills up. The distillation is continued until around 0.5mL of distillate is collected, at which point the heat is turned off. 11. The apparatus is lifted from the aluminum block to let it cool.12. A long-stem Pasteur pipette is used to transfer the distillate from the still head to a clean test tube. 13. The product is dried for about 5 minutes over anhydrous sodium sulfate, using just enough to make a thin layer at the bottom of the test tube. 14. A clean Pasteur pipette is used to transfer the dried liquid to a clean test tube for GC analysis.15. The sample is corked and taken into the instrument room in order to run the GC.

GC Collection16. The sample is prepared for injection by using a microsyringe to collect between 1 and 5 microliters of the sample in the syringe, then 3-4 microliters of air. 17. “Run Acquisition”is clicked on the computer screen. 18.MOVE THE VIEW TOWARD THE RIGHT TO SEE THE INJECTION.19. The needle is inserted all the way into the GC portand in one smooth motion, the sample is injected into the GC. 20. Observe the chromatogram on the computer screen to the right as it’s being collected. 21. Click“Stop Acquisition/Print Gas Chromatogram”, then analyze the gas chromatogram.