Organic Chemistry I Lab Acetylation of Aniline and Purification of Acetanilide

1. Organic Chemistry I LabAcetylation of AnilineandPurification of Acetanilide Follow the procedure given in the lab manual for this experiment. Check also various techniques utilized.

2. You will be given two vials for the experiment:** The vial with the dark liquid contains 2 mL of aniline** The vial with the transparent liquid contains 2.5 mL of acetic anhydride

3. Upon mixing the contents of the vials in a 125 mL erlenmeyer flask with 15 mL of water, the product will form after a little bit of swirling.

4. After the product is formed, add more water and heat until the product dissolves

5. When the water solution ceases boiling, ***pour about 1 mL of the solution into a clean beaker and keep it***add charcoal to the solution (carefully –frothing may occur)***bring the solution to boiling again and keep it boiling for a few minuteskeep the charcoal solution hot throughout the filtering process

6. Preparation of the collecting flask • It is necessary that the collecting flask and the filter paper is kept hot to prevent the product from recrystallizing on the filter paper.

7. Preparation of the collecting flask • Add 10 mL of “hot” distilled water through the fluted filter paper into the collecting flask • Discard the water from the flask (once the filter paper, the funnel and the flask are warmed)

8. Filtering Add the hot charcoal solution through the fluted filter paper into the flask (a little at a time)

9. Notebook Write-up Give the title of the experiment Give the chemical reaction Give the names of the materials (under the reaction) Give the quantities of each of the starting materials used in the reaction (both in mL and in mmol) Remember this experiment is a synthesis, but it also utilizes a “physical method” (charcoal treatment and recrystallization) to purify the product. You should decide yourselves what the most significant purpose of the experiment is.

10. Notebook Write-up You should have the following sections in your notebook for this experiment: Objectives: Materials: Hazards: Procedure: Results: Discussion and Questions:

11. Notebook Write-upMaterials There is no need for a separate entry, if you use the chemical reaction for this purpose

12. Notebook Write-upHazards You should look up all the possible hazards of the materials you are using and also comment how you intend to protect yourself against any of these (for example, if any of the materials you are using are skin irritants, you can overcome this hazard considerably by wearing gloves) List and discuss only the relevant hazards for you in the lab

13. Notebook Write-upProcedure Do not copy the procedure from the lab manual. Write a brief outline of the procedure. However, make sure to indicate clearly if you deviate from what is written in the lab manual

14. Notebook Write-upData All the data in this experiment can be written in the “Results” section.

15. Notebook Write-upResults This is the most important section (as always). You have two types of results for this experiment: 1. Melting points of the (i) unpurified and (ii) charcoal purified product 2. Experimental yield (mass of your product). However, you will not be able to measure either of these physical properties until next week when your product is totally dry.

16. Notebook Write-upDiscussion and Questions Calculate the theoretical yield and the percentage yield for the synthesis. Comment on the purity of your product based on the comparison of the melting points you measured with literature melting points. Answer the questions assigned.

17. HAVE FUN