Reaction of alkyl halides with strong unhindered bases

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SUMMARY

The discussion centers on the reaction of primary alkyl halides with strong unhindered bases, specifically ethoxide (EtONa). Participants express confusion regarding the solution manual's assertion that the sole product is an alkene, questioning the omission of the SN2 reaction that should occur in significant quantities. The conversation highlights the role of steric hindrance in determining reaction pathways, particularly referencing neopentyl structures as a comparison. Ultimately, the consensus is that while elimination to form alkenes is favored, SN2 reactions can still occur under the right conditions.

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  • Understanding of alkyl halide reactivity
  • Knowledge of SN2 and elimination (E2) reaction mechanisms
  • Familiarity with steric hindrance concepts
  • Basic knowledge of organic reaction conditions and reagents
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  • Research the effects of steric hindrance on nucleophilic substitution
  • Examine examples of primary alkyl halides reacting with strong bases
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Chemistry students, organic chemists, and educators seeking to deepen their understanding of alkyl halide reactions and the influence of steric factors on reaction pathways.

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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There is no other SN2 reaction. There aren't any other leaving groups.
 
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.
 

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