EK Orgo In-Class Lecture 2 #29

[dougkaye]

EK is saying that (S)-sec-butyl-chloride will react with NaOH in a Sn2 reaction and therefore the carbon will have inversion of configuration. I believe tertiary alkyl halides will almost always go Sn1 because of the stability of the carbocation. Any ideas?

FYI in EK (2007) orgo, they specifically say that tertiary substrates will not undergo Sn2. So I'm guessing this is errata, oh well.

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[Godric]

EK is saying that (S)-sec-butyl-chloride will react with NaOH in a Sn2 reaction and therefore the carbon will have inversion of configuration. I believe tertiary alkyl halides will almost always go Sn1 because of the stability of the carbocation. Any ideas?

(S)-sec-butyl-chloride Is a 2° substrate, and NaOH is a strong Nuc so it can go Sn2, and the resulting reaction would produce a product that has inversion of chemistry.

Image via; chemblink


I am in agreement with you when you say that, a 3° substrate will (almost) always got Sn1 because it prefers to form the 3° carbocation because it more stable.

Hope I helped, I believe your mistake was in thinking that the substrate was 3° when it was 2°. If I am wrong about anything, I do apologize, I am just trying to help.

 

[shffl]

Secondary and tertiary alkyl halides will most of the time undergo SN1 reactions. However, if the nucleophile used is strong the reaction will almost always be SN2.

 

[dougkaye]

no you're exactly right! i need to review those butyl groups. i got confused b/t sec-butyl and tert-butyl thank you.