ASP Iodination of Salicylamide Report

write a Report about the experiment.

on the files attached the procedure and observation

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ASP Iodination of Salicylamide Report
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CHM 2012 Experiment 1: Iodination of Salicylamide1
1) Prepare an ice bath for use later in the experiment.
2) Calculate the mass of 7.5 mmol of salicylamide and then weigh that amount.
Record the exact mass used and then transfer the weighed salicylamide to a
125-mL Erlenmeyer flask.
3) Add 20-mL of absolute ethanol to the Erlenmeyer flask and swirl the mixture until
all salicylamide is dissolved.
4) Calculate the mass of 8.0 mmol of sodium iodide and then weigh that amount.
Dissolve the weighed sodium iodide in the Erlenmeyer flask completely.
5) Place the Erlenmeyer flask in the prepared ice bath and allow the reaction
mixture to cool to 0°C (approximately 5 minutes).
6) After sufficient cooling remove the reaction mixture from the ice bath and
immediately add 10-mL of 6% sodium hypochlorite solution.
7) Gently swirl the flask and then allow the reaction mixture to rest undisturbed for
10-15 minutes. Record visual observations during this time.
8) If the reaction mixture does not achieve a pale-yellow coloration in 15 minutes
add another 5-mL of 6% sodium hypochlorite solution and allow the reaction to
occur for another 5-10 minutes.
9) Once the reaction mixture has become pale-yellow in color add 10-mL of 10%
(w/v) aqueous sodium thiosulfate to remove any excess iodine.
10) Carefully add 1 M hydrochloric acid dropwise to acidify the reaction mixture.
Check the pH periodically with pH paper strips. Record any visual observations
as a white precipitate is formed.
11) Cool this reaction mixture and a bottle of deionized water in an ice bath.
12) Collect the precipitate using vacuum filtration. Setup a Büchner funnel atop a
vacuum flask using the appropriate adapter to seal the vacuum. Ask your GSA if
you have questions on this setup before proceeding.
13) Place the appropriately sized filter paper inside the Büchner funnel. Apply the
vacuum and gently rinse the filter paper with a small amount of cold deionized
water before adding the reaction mixture.
14) Add the reaction mixture to the Büchner funnel slowly. Attempt to keep the
solution inside of the filter paper in order to prevent any loss of product around
the edges.
15) Record the mass of your product and calculate the percent yield for the reaction.
16) Recrystallize this crude product in 95% ethanol if time permits. Record the mass
of the recrystallized product. Calculate the recovery percent using the masses of
recrystallized and crude products. Ask your GSA whether this step will be
possible in the time left or about how to conduct the recrystallization procedure.
17) Collect the IR spectrum of your final product from either step (#15 or #16) with
help from your GSA. Provide a small sample of your product to your GSA for
additional analysis by NMR. You will receive specific instructions for these steps.
1) Davidson, T. Electrophilic Aromatic Substituion. In CHM2211L/2200L Organic
Chemistry Lab Manual, 2022-2023 ed.; Hayden-McNeil, 2022; pp 59-64.
When we add sodium hypochlorite it appears a dark brown color. We sit it for about 10-15 mins
in 4 mins it is getting lighter yellow color.
We add 3 drops of hydrochloric acid into our solution we keep adding 3 more drop after 30
drops we get the sparkling on the bottom.
We check the solution with pH paper, and we get (10pH)
0.21g mass of filter paper
0.30g mass of the product
We add more drops of hydrochloric acid because we need to get higher mass for our product
0.21-0.42= -0.21
263g/mol*7.5mol/1.97=0.30g/1.97*100=15.22 our product mass
Melting point:
Start melting 195
Fully melting 201
We get 0% recovery

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