Organic Chemistry I LabOrganic Chemistry I LabAcetylation of AnilineAcetylation of Aniline

andandPurification of AcetanilidePurification of Acetanilide

Follow the procedure given in the lab Follow the procedure given in the lab manual for this experiment. Check manual for this experiment. Check also various techniques utilized.also various techniques utilized.

You will be given two vials for the You will be given two vials for the experiment:experiment:** ** The vial with the dark liquid contains 2 mL of The vial with the dark liquid contains 2 mL of

anilineaniline ** ** The vial with the transparent liquid contains The vial with the transparent liquid contains 2.5 mL of acetic anhydride2.5 mL of acetic anhydride

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

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

When the water solution ceases boiling, When the water solution ceases boiling, ***pour about 1 mL of the solution ***pour about 1 mL of the solution into a clean beaker and keep itinto a clean beaker and keep it***add charcoal to the solution ***add charcoal to the solution ((carefully –frothing may occurcarefully –frothing may occur))***bring the solution to boiling again ***bring the solution to boiling again and keep it boiling for a few and keep it boiling for a few minutesminutes

keep the charcoal solution hot keep the charcoal solution hot throughout the filtering processthroughout the filtering process

Preparation of the collecting flaskPreparation of the collecting flask

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

Preparation of the collecting flaskPreparation of the collecting flask

Add 10 mL of “hot” distilled water through the Add 10 mL of “hot” distilled water through the fluted filter paper into the collecting flaskfluted filter paper into the collecting flask

Discard the water from the flask (once the Discard the water from the flask (once the filter paper, the funnel and the flask are filter paper, the funnel and the flask are warmed)warmed)

FilteringFiltering

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

Notebook Write-up Notebook Write-up

•Give the title of the experimentGive the title of the experiment•Give the chemical reactionGive the chemical reaction•Give the names of the materials (under the reaction)Give the names of the materials (under the reaction)•Give the quantities of each of the starting materials used in the Give the quantities of each of the starting materials used in the

reaction (both in mL and in mmol) reaction (both in mL and in mmol)

Remember this experiment is a synthesis, but it also utilizes a Remember this experiment is a synthesis, but it also utilizes a “physical method” (charcoal treatment and recrystallization) to “physical method” (charcoal treatment and recrystallization) to purify the product. purify the product. You should decide yourselves what the most significant purpose You should decide yourselves what the most significant purpose of the experiment is.of the experiment is.

Notebook Write-up Notebook Write-up

You should have the following sections in your You should have the following sections in your notebook for this experiment:notebook for this experiment:

Objectives:Objectives:

Materials:Materials:

Hazards:Hazards:

Procedure:Procedure:

Results:Results:

Discussion and Questions:Discussion and Questions:

Notebook Write-upNotebook Write-upMaterials Materials

There is no need for a separate entry, if you use There is no need for a separate entry, if you use the chemical reaction for this purposethe chemical reaction for this purpose

Notebook Write-upNotebook Write-upHazards Hazards

You should look up all the possible hazards of You should look up all the possible hazards of the materials you are using and also comment the materials you are using and also comment how you intend to protect yourself against any of how you intend to protect yourself against any of these (for example, if any of the materials you these (for example, if any of the materials you are using are skin irritants, you can overcome this are using are skin irritants, you can overcome this hazard considerably by wearing gloves)hazard considerably by wearing gloves)

List and discuss only the relevant hazards for you List and discuss only the relevant hazards for you in the lab in the lab

Notebook Write-upNotebook Write-upProcedure Procedure

Do not copy the procedure from the lab manual.Do not copy the procedure from the lab manual.

Write a brief outline of the procedure. However, Write a brief outline of the procedure. However, make sure to indicate clearly if you deviate from make sure to indicate clearly if you deviate from what is written in the lab manualwhat is written in the lab manual

Notebook Write-upNotebook Write-upData Data

All the data in this experiment can be written in All the data in this experiment can be written in the “Results” section.the “Results” section.

Notebook Write-upNotebook Write-upResults Results

This is the most important section (as always). This is the most important section (as always). You have two types of results for this experiment:You have two types of results for this experiment:

1. Melting points of the1. Melting points of the(i) unpurified and(i) unpurified and(ii) charcoal purified product(ii) charcoal purified product

2. Experimental yield (mass of your product).2. Experimental yield (mass of your product).

However, you will not be able to measure either of these However, you will not be able to measure either of these physical properties until next week when your product is physical properties until next week when your product is totally dry.totally dry.

Notebook Write-upNotebook Write-upDiscussion and Questions Discussion and Questions

Calculate the theoretical yield and the percentage yield Calculate the theoretical yield and the percentage yield for the synthesis.for the synthesis.

Comment on the purity of your product based on the Comment on the purity of your product based on the comparison of the melting points you measured with comparison of the melting points you measured with literature melting points.literature melting points.

Answer the questions assigned.Answer the questions assigned.

HAVE FUNHAVE FUN