Can an SN2 reaction occur in the presence of CH3OH, a protic solvent? I understa

Question

Can an SN2 reaction occur in the presence of CH3OH, a protic solvent? I understand SN2 strongly favors aprotic solvents.

So take this question for instance:

CH3CH2Cl- + NaOCH- -----> ?

The solvent used is CH3OH.

We have a strong nucleophile, a good leaving group, but we're faced with a protic solvent. Is there a hierarchy of priority? Chegg solutions says it does occur, but my textbook also states that it's extremely difficult as the nucleophile would go for the H+ ions in the protic solvent as opposed to the cation which doesn't have a full positive charge like the H+ ions. Who is right?

Explanation / Answer

tertiary alkyl halides -----> SN1 reaction favours------ protic solvents.

Secondary alkyl halides ------> SN1 reaction favours ----Protic solvent / SN2 reaction favours ----Aprotic solvent.

Primary akyl halides ------> SN2 reaction favours --- aprotic solvent.

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