Reaction of alkyl halides with strong unhindered bases

In summary, the conversation discusses a question about a reaction involving a primary alkyl halide and an unhindered base. The solution manual only considers the formation of the alkene product, but the individual is curious about why the SN2 reaction is not taken into consideration. The individual suggests that steric hindrance may play a role in the lack of SN2 reaction. However, there are no other leaving groups present in the reaction. The individual is unsure of the exact reason and is interested in a better explanation.
  • #1
alingy1
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Please look at the image. For (b) and (c), what the solution manual says makes no sense to me.
You're reacting a primary alkyl halide with an unhindered base EtONa. They say that the only product is the alkene. Why do they not consider the SN2 reaction that WILL take place in larger quantity?
I'm uploading the question too.
 

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  • #2
There is no other SN2 reaction. There aren't any other leaving groups.
 
  • #3
I am actually not too sure, but I think it is due to the steric hinderance. The hinderance does not always have to be on the beta carbon, if you compare the structure to a neopentylic structure, which can never participate in an Sn2, there are similarities, except that there are only two metyl substituents, instead of three.

In all honesty, if I would not have known the answer i would have gone for Sn2 as well so I would also love to see a good explanation.
 

1. What is the reaction of alkyl halides with strong unhindered bases?

The reaction of alkyl halides with strong unhindered bases is a type of nucleophilic substitution reaction, where the alkyl halide is replaced by a nucleophile. The strong, unhindered base acts as the nucleophile and attacks the carbon bonded to the halide, displacing the halogen atom and forming a new bond with the carbon.

2. What is the role of strong unhindered bases in this reaction?

The role of strong unhindered bases in this reaction is to act as the nucleophile and initiate the substitution reaction. These bases are able to easily donate an electron pair and attack the alkyl halide due to their strong basicity and lack of bulky substituents.

3. What are some examples of strong unhindered bases used in this reaction?

Some common examples of strong unhindered bases used in this reaction include sodium hydroxide (NaOH), potassium hydroxide (KOH), and sodium amide (NaNH2). These bases have strong basicity and lack bulky substituents, making them effective nucleophiles for the substitution reaction.

4. What factors influence the reactivity of alkyl halides with strong unhindered bases?

The reactivity of alkyl halides with strong unhindered bases can be influenced by factors such as the strength of the base, the steric hindrance of the alkyl halide, and the solvent used. Stronger bases and less sterically hindered alkyl halides will generally have a faster reaction rate.

5. What are the potential products of this reaction?

The potential products of this reaction are the substituted alkyl halide and the corresponding base. Depending on the reactants and reaction conditions, different products may be formed, such as a primary, secondary, or tertiary alkyl halide. In some cases, elimination reactions may also occur, leading to the formation of alkenes.

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