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A S
N
2 Reaction using Greener Approach Shannon Scott
Section 602
Shanelle Suepaul
08/30/2022
Introduction:
The purpose of this lab is complete and Sn2 reaction in a safe and easy way. In order to perform this reaction a greener approach is the best approach. The greener approach would be done with 1-iodobutane and 2-naphthol. In order to minimize the hazardous solvents that are being used ethanol will be used as a solvent. If a greener approach is done, then the Sn2 reaction will be completed in a safe way to produce 2-butoxynaphthalene.
Materials:
- Lab coat
- Scrub pants
- Lab goggles - Round bottom flask(100ml)
- 50 mL of water
- 25 g of ice
- 25 mL beaker
- Reflux condenser
- Scale
- Filter paper
- Boiling chips
- Suction filtration
- Timer
- 0.56 g of NaOH (6 pellets)
- 1.0 grams of 2-naphthol - 1.0 ml of 1-iodobutane
Safety- NaOH: Causes severe skin burns and eye damage. Causes serious eye damage and is highly flammable. 2-naphthol: causes serious eye damage, skin corrosion and is flammable. 1-
iodobutane: causes Sears eye damage, skin irritation, and it’s highly flammable.
Procedure:
Take a 100 mL round Flask and add 0.56g of NaOH and 10g of 2-naphthol. Add 20ml of ethanol
to the flask and swirl. Reflux the solution for 15 minutes. Then take the flask off the heat and allows it to cool before removing it from the reflux condenser. Now add in 1ml 1-iodobutane and
put it on the condenser and reflux it for an hour. While waiting for the hour to pass get 50ml of water and put it to the side. After the hour remove from the heat and pour it over 25g of ice in a 250ml beaker. Swirl beaker until the ice melts. Then pour solution over the filter paper in the suction filtration to collect product. Then wash product with cold water and let it air dry for 5-10 minutes. Allow the product to dry for a week then taking the weight of the product and calculate the percent yield.
Date:
Compound
Mass (g)
NaOH
0.56
2-Naphtol
1.002
Crystal
Mass (g)
2-butoxyanphthalene
0.731
Results/Calculations:
2-naphthol= 1.00
g
144.17
g
/
mol
=
0.0069
mols
Density of iodobutane =
1.62
g
184.02
g
/
mol
=
0.0088
g
Theoretical yield= 0.0069 mol x 200.28 g/mol = 1.38g (2- butoxyanphthalene)
Percent yield = Actual
Theoretical
x
100
=
0.731
g
1.38
g
x
100
=
52.97%
Figuers:
Analysis:
In the substitution reaction the naphthoxide was the nucleophile this was produced by 2-
naphthol and NaOH reacting with each other. The reaction yielded the butylnaphthyl ether and sodium iodide. The percent yield of the final product was 52.97%. This percent yield was rather low so that only means that there were some errors in the experiment. One issue that could’ve taken place was that we probably didn’t allow the reaction to finish completely because we took it out of the heat source exactly at one hour and it might have needed more time to complete the reaction. another reason for the low percent yield could be because of the solvent that was used. In this experiment we used ethanol as a solvent. Ethanol is typically not used in a SN2reaction because it slows down the reaction. In order to conduct an SN2 reaction A polar a protic solvent
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must be used. In this case we use the polar protic solvent. when we were starting the filtration process, we poured out our solution onto the filter paper but there was still some of the solution residue on the beaker so we weren’t able to get all of the solution into the filtration system to filter. So, because of that it caused us to have a low percent yield. This experiment could’ve been
better if we didn’t have as many technical and human errors when doing the experiment.
Post lab question:
1. In an SN2 reaction it prefers to have a solvent that is polar aprotic. THF is the preferred polar aprotic solvent for SN2 reactions. In this experiment the polar aprotic solvent is not the ethanol. Ethanol is polar protic so in this experiment it slows down the SN2 reaction and then the hydrogen bonds to the nuclear file which makes it less effective on attacking the substrate. So, using ethanol as a solvent would make the reaction less favorable since ethanol would bond with perform a hydrogen bond with the nucleophile make it less reactive.
2.It is important to mix the naphthol with sodium hydroxide before adding the electrophile because hydrogen bonding will occur. Naphthol Will be protonated by sodium hydroxide which creates a good leave in group for naphthol. Then the ethanol will attack naphthol end it will de protonated allowing naphthol to have lone pairs.
3.
Out of the two nucleophiles sodium naphtoxide would be better because the oxygen will have a negative charge as opposed to the naphtol having a neutral charge.
4. This reaction is considered a greener SN2 reaction because it occurred under a less hazardous condition. this reaction is safe for the environment because it requires less hazardous chemicals.
Reference:
Approaches to Incorporating Green Chemistry and Safety into Laboratory Culture
Natalie J. O’Neil, Star Scott, Rachael Relph, and Ettigounder Ponnusamy
Journal of Chemical Education
2021
98
(1), 84-91
DOI: 10.1021/acs.jchemed.0c00134
SN2
. Chemistry LibreTexts. (2022). Retrieved 4 September 2022, from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/
Supplemental_Modules_(Organic_Chemistry)/Reactions/Substitution_Reactions/SN2
.
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