Christopher Moore

Partner: Nick Sievers

Dr. Anderson

CHE-2151

Performed 10/09/2017

SN2 Reaction, Reactions of Alkyl Halides

The focus of Experiment 7 is to discuss the differences between SN1 and SN2 reactions.

Specifically, it looks at which reactions are more likely to occur based on the chemical properties

of the reagents. SN1 reactions occur in a stepwise process. They’re more likely to occur with

methyl and primary alkyl halides. They also prefer a apolar protic solvent. SN2 reactions occur

in a concerted process. They prefer tertiary alkyl halides, and highly prefer protic nonpolar

solvents.

This experiment creates situations in which methyl, primary, secondary, and tertiary alkyl

halides are treated with halides in protic apolar and protic nonpolar solvents. By doing this, we

can observe what reactions occur to prove the differences between SN1 and SN2 reactions. The

reagents tested include 1-chlorobutane, 1-bromobutane, 2-chlorobutane, 2-chloro-2-

methylpropane, bromobenzene, 2-chloro-2-methylpropane, 1-chloro-2-butene (mix of cis and

trans isomers), 1-chloro-2-methylpropane, 2-bromobutane, 2-bromo-2-methylpropane

These can be organized into primary, secondary, and tertiary alkyl halides

Primary: 1-chlorobutane, 1-bromobutane, 1-chloro-2-methylpropane

Secondary: 2-chlorobutane, 2-bromobutane, and bromobenzene,

Tertiary - 2-chloro-2-methylpropane, 2-bromo-2-methylpropane

As well as 1-chloro-2-butene with its double bond.

 Two solvents are used in testing these reagents. Sodium Iodide, a polar protic solvent is

used to test for a SN2 reaction, where ethanolic silver is intended for SN1 reactions. These

solvents were added and observed for 5 minutes for rate of reaction. If no reaction occurred, they

were added to a 50 degree Celsius water bath for 5 minutes and observed after. The heat

increases the rate at which the reaction occurs, allowing for reactions that are non-spontaneous.

Our results showed that all of the primary alkyl halides reacted with heat in the presence

of Ethanolic Silver, and did not react with sodium iodide. This is consistent with the properties of

SN1 reactions favoring non-polar protic solvents and primary alkyl halides. Therefore, these

reagents underwent SN1 reactions, but not SN2 reactions.

Our secondary alkyl halides all reacted differently based on their size. 2-bromobutane

reacted quickly in both ethanolic silver and sodium iodide, being capable of both SN1 and SN2

reactions. 2-chlorobutane reacted with heat in the presence of ethanolic silver, but not with

sodium iodide. 1-chloro-2-methylpropane did not react at all. This suggests that secondary alkyl

halides are dependant on their chemical makeup to determine what reactions they will or will not

perform.

Our tertiary alkyl halides both reacted quickly with ethanolic silver, however 2-bromo-2-

methylpropane did not react in the presence of Sodium iodide. This aligns with chlorine being

more electronegative, and therefore more polar, and more likely to react with polar solvents.

Our results were consistent with other groups for most of the reagents. Some groups

found that certain reagents reacted faster, but this could be accounted for based on human error

when adding the amount of substrate, as this would affect the rate of the reaction in both SN1

and SN2 reactions. Overall, the experiment demonstrated the properties of SN1 and SN2

reactions very closely to the text.