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  • Published on: 15th October 2019
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Introduction

There is a diverse array of organic reactions, classified mainly by the mechanism with which they react. Two of which are pertinent to this topic: Sn1 and Sn2. An Sn2 reaction is characterized by a nucleophile bonding with a carbon in a molecule as a leaving group simultaneously detaches from the carbon. In an Sn1 reaction, the leaving group initially leaves the molecule in a slow step, then the nucleophile is introduced in its place in a fast step. Various components can affect the rate of Sn1 and Sn2 reactions, such as the type of leaving group, the structure of the molecule, and in the case of Sn2 only, the concentration of the nucleophile (2). The reaction that produces tert-Butyl Chloride in this experiment is an Sn1 reaction, because it has a fast and slow step in its reaction (1). There is a possible side product that may be produced during this experiment, which would produce an alkene with two methyl groups, and hydrochloric acid.

Experimental Section

Table of Chemicals

Hydrochloric Acid: HCl, 36.5 g/mol (3)

Color: Colorless

Hazards: Very hazardous if skin contact, eye contact, ingested; hazardous if inhaled.

Tert-Butyl Alcohol: (CH₃)₃COH, 74.123 g/mol (4)

Boiling Point: 83o C

Melting Point: 26o C

Hazards: Flammable, very hazardous if ingested, causes respiratory irritation

1-Chlorobutane: CH3(CH2)3Cl, 92.566 g/mol (5)

Boiling Point: 79o C

Melting Point: -123o C

Hazards: Flammable, irritant

Sodium Iodide: NaI, 184.894 g/mol (6)

Boiling Point: 1304o C

Melting Point: 651o C

Hazards: Irritant

Silver Nitrate: AgNO3, 169.872 g/mol (7)

Boiling Point: 440o C

Melting Point: 212o C

Hazards: Oxidizer, causes eye and skin damage

Results

Test Tube Time

1 (NaI in t-butyl chloride) >10 min

2 (AgNO3 in t-butyl chloride) Instant

3 (NaI in 1-chlorobutane) Instant

4 (AgNO3 in 1- chlorobutane) >10 min

Calculations

(5 mL * .781 g/ml)/ 74.123 g/mol) = .0527 mol tert-butyl alcohol

Theoretical Yield = .0527 * (1mol t-butyl chloride/1mol t-butyl alcohol) * 92.57 g/mol = 4.88g

We yielded 1.23 grams

1.23g / 4.88g = .252 = 25.2% yield

Discussion

The reaction in test tube 1 between sodium iodide and tert-butyl chloride progressed very slowly, because tert-butyl chloride is a tertiary alkyl halide, which reacts poorly with sodium iodide. This is why sodium iodide formed a quick precipitate with 1-chlorobutane: it is now reacting with a primary alkyl halide. Silver nitrate, on the other hand, reacts well with tertiary alkyl halides (1), so, it quickly formed a precipitate with tert-butyl chloride, and not with 1-chlorobutane. The shape of a substrate is actually quite instrumental in determining what it reacts best with. If the shape somehow deters the nucleophile from accessing the carbocation, then the reaction does not occur as readily. Also, interestingly enough, an increase in the concentration of a solvent can slow a reaction because it blocks nucleophiles from getting to the carbocation (2).

Conclusion

The data from the lab not only shows that the method we employed to produce tert-butyl chloride is reliable, but that the structure of a substrate can be taken into consideration when performing analytic procedures to determine whether you have actually produced the intended chemical.

Works Cited

Weldegirma, S. Experimental Organic Chemistry; University of South Florida: Tampa, 2018. (1)

Solomons, T. W. G.; Fryhle, C; Snyder, S. Organic Chemistry, 12th Edition; Wiley: Hoboken, NJ, 2016 (2)

Hydrochloric Acid; [Online]; Sciencelab: Houston, TX, October 10th, 2005. http://www.sciencelab.com/msds.php?msdsId=9924285 (accessed 10/16/2018). (3)

Tert-Butyl Alcohol; [Online]; PubChem: Bethesda, MD, https://pubchem.ncbi.nlm.nih.gov/compound/6386 (accessed 10/16/2018) (4)

1-chlorobutane; [Online]; PubChem: Bethesda, MD, https://pubchem.ncbi.nlm.nih.gov/compound/8005 (accessed 10/16/2018) (5)

Sodium Iodide; [Online]; PubChem: Bethesda, MD, https://pubchem.ncbi.nlm.nih.gov/compound/5283 (accessed 10/16/2018) (6)

Silver Nitrate; [Online]; PubChem: Bethesda, MD, https://pubchem.ncbi.nlm.nih.gov/compound/24470 (accessed 10/16/2018) (7)

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