Lab 7 Nucleophilic Substitution Lab

Lab 7: Nucleophilic Substitution CHEM 3301 April 2, 2024 Julianne Santiago and Breanna Delgadillo

Abstract Different mechanisms proceed at different rates and this can be due to many different factors such as nucleophile strength, solvent strength, and good leaving group. SN1 and SN2 are kinetic reactions, but also have differences from one another. Occasionally, some reactions favor one mechanism over the other and are able to form a precipitate if soluble in either ethanol or acetone. It was viewed that SN2 solvent and mechanism overall is most favorable for alkyl chloride, benzyl chloride, 1-bromobutane. Meanwhile, the SN1 mechanism was most favorable for tert-butyl bromide.

Introduction Organic chemistry is the study of organic …show more content…
This would mean the reaction happened almost instantly, which matches the timing the precipitate formed. For alkyl chloride, precipitate starts to form about 3 seconds after adding the solvent to start forming precipitate. Meanwhile, the 1-bromobutane and benzyl chloride took about 5 seconds to form a precipitate. Although, it is important to note that benzyl chloride was also able to form precipitate within the SN1 solvent, AgNO3 in ethanol after the addition of heat. This may imply that benzyl chloride can proceed through a SN1 or SN2 mechanism, but one is more favorable than the other. In this case SN2 is favored due to the stability the benzyl ring provides and it provides a strong nucleophile and leaving group which is essential to SN2 reactions. Similarly, 2-bromobutane showed signs of precipitation in the SN2 solvent, NaI/Acetone, likewise to benzyl chloride, precipitate was formed after about 30 seconds with the addition of heat. Conversely, it also showed a slight appearance of precipitation, though not as enhanced in the SN1 solvent, AgNO3/Ethanol. Generally, 2-bromobutane may show a greater tendency towards SN2 reactions, but under certain conditions, SN1 reactions can also occur. As for tert-butyl bromide, when reacted with AgNO3 with the presence of …show more content…
Each one has a different rate and it all can be drawn back to the first step in each mechanism. Everything that was supposed to have a reaction was able to react properly, indicating that there are certain compounds that favor one mechanism over the other. Alkyl halides with a primary carbon tend to favor most SN2 reactions considering they are highly unstable due to its steric hindrance and SN2 is the only way it could stabilize itself productively. Meanwhile, SN1 reactions are generally favorable for alkyl halides with tertiary carbons due to the stability of the carbocation intermediate formation in the reaction. As for secondary alkyl halides, they can undergo both SN1 and SN2 reactions, depending on its specific conditions. However, due to the steric hindrance surrounding the reacting carbon, the formation of a stable carbocation intermediate becomes less favorable, and likely to favor SN2 reactions to a certain

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