Determining SN1/SN2 Balance for 2-Bromobutane Formation

In summary: Now, if this was 1-bromobutane, I know it would be via an SN2 reaction (steric hindrance)But since 2-bromobutane rests right in the middle, where do I find this balance? It would be a little bit of both the carbocation and steric hinderance involved, wouldn't it?In summary, for a compound with a secondary alpha carbon, you would get 2-butanol (via nucleophillic substitution) or t-butanol (via carbocation) if it was 1-bromobutane. If it was 2-bromobutane, it would be via an SN2 reaction.
  • #1
soggybread
20
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For example, if we have 2-butanol, a compound with a secondary [tex]\alpha[/tex] carbon and
I reacted this with HCl and NH4Br

I would get 2-bromobutane (via nucleophillic substitution), but how would I determine whether this goes via SN1 or SN2 to achieve this?

Now, if this was 1-bromobutane, I know it would be via an SN2 reaction (steric hindrance)
And if it was t-bromobutane, it would be via an SN1 reaction (carbocation)

But since 2-bromobutane rests right in the middle, where do I find this balance? It would be a little bit of both the carbocation and steric hinderance involved, wouldn't it?

My question:
I've found some SN1/SN2 tables online (i.e. http://www.cem.msu.edu/~reusch/VirtualText/alhalrx3.htm#hal9) , which seem to point that 2-bromobutane should undergo SN2, because Br- is a weak base.


But does that mean literally 100% of this entire reaction goes through SN2 then?
Or is there a small ratio, like 95% SN2, and 5% SN1, but small enough to assume that SN2 is the entire reaction mechanism?

Thanks for clearing this up.
 
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  • #2


soggybread said:
For example, if we have 2-butanol, a compound with a secondary [tex]\alpha[/tex] carbon and
I reacted this with HCl and NH4Br

I would get 2-bromobutane (via nucleophillic substitution), but how would I determine whether this goes via SN1 or SN2 to achieve this?

Consider what would happen here if you had, for instance (R)-butan-2-ol. What would be the product by SN1, or by SN2, and how do they differ?
 
  • #3


Protonating the alcohol makes it a wonderful leaving group. Excess acid converts the water into H3O+ and prevents it from adding back. Seems like you would get a little of SN1 and SN2. Maybe a couple of percent of the SN1 product. Solvent has an effect as well. How might a less polar solvent affect the outcome?
 

1. What is SN1/SN2 balance and why is it important in the formation of 2-bromobutane?

SN1/SN2 balance refers to the relative proportions of SN1 and SN2 reactions that occur during a chemical reaction. In the formation of 2-bromobutane, the balance between these two reaction mechanisms is important because it determines the yield and purity of the final product.

2. How do you determine the SN1/SN2 balance for 2-bromobutane formation?

The SN1/SN2 balance can be determined by conducting a kinetic study of the reaction. This involves monitoring the rate of the reaction under different conditions and analyzing the resulting data to determine the rate constants for both SN1 and SN2 reactions. The ratio of these rate constants is used to calculate the SN1/SN2 balance.

3. What factors influence the SN1/SN2 balance for 2-bromobutane formation?

The SN1/SN2 balance can be influenced by several factors, including the nature of the substrate, the solvent, and the presence of any nucleophilic or protic species. The steric hindrance of the substrate and the strength of the electrophile also play a role in determining the balance.

4. How does the SN1/SN2 balance affect the yield and purity of 2-bromobutane?

The SN1/SN2 balance can affect the yield and purity of 2-bromobutane in several ways. A higher proportion of SN2 reactions generally leads to a higher yield of the desired product, while a higher proportion of SN1 reactions can result in the formation of unwanted byproducts. Additionally, SN2 reactions tend to yield a purer product, while SN1 reactions can result in a mixture of stereoisomers.

5. Can the SN1/SN2 balance be controlled or manipulated?

Yes, the SN1/SN2 balance can be controlled and manipulated by adjusting the reaction conditions. For example, using a more polar solvent can favor SN1 reactions, while using a less polar solvent can favor SN2 reactions. Additionally, changing the concentration of nucleophilic or protic species can also influence the SN1/SN2 balance.

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