Determining SN1/SN2 Balance for 2-Bromobutane Formation

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The discussion centers on the formation of 2-bromobutane from 2-butanol through nucleophilic substitution, specifically evaluating the balance between SN1 and SN2 mechanisms. It is established that 2-bromobutane can be formed via both pathways due to the secondary nature of the carbon, with factors such as steric hindrance and carbocation stability influencing the reaction. The consensus indicates that while SN2 is the predominant mechanism due to the weak basicity of Br-, a minor SN1 pathway may also occur, potentially around 5%. The role of solvent polarity is also highlighted as a significant factor affecting the reaction outcome.

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For example, if we have 2-butanol, a compound with a secondary \alpha 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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soggybread said:
For example, if we have 2-butanol, a compound with a secondary \alpha 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?
 


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?
 

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