Home >
Community >
Do secondary alcohols prefer to undergo SN1 or SN2 reactions when reacting with a strong acid?
Upvote
20
Downvote
+ Alcohols
+ Chemistry
Posted by
Martin Reyto
Do secondary alcohols prefer to undergo SN1 or SN2 reactions when reacting with a strong acid?
Actually, secondary alcohols undergoes $\mathrm{S_N1}$ or $\mathrm{S_N2}$ depending upon the substrate you are using. For e.g. In your case(as provided above) the substrate has steric hindrance nearby alcoholic group and the carbocation will be stable due to the migratory aptitude of the methyl group. Hence, here should be $\mathrm{S_N1}$ and you have to see the structure of substrate to decide $\mathrm{S_N1}$ or $\mathrm{S_N2}$ for secondary alcohols.
Also, alcohols are not good leaving groups also! But after protonation the water is a very good leaving group.
Actually, secondary alcohols undergoes $\mathrm{S_N1}$ or $\mathrm{S_N2}$ depending upon the substrate you are using. For e.g. In your case(as provided above) the substrate has steric hindrance nearby alcoholic group and the carbocation will be stable due to the migratory aptitude of the methyl group. Hence, here should be $\mathrm{S_N1}$ and you have to see the structure of substrate to decide $\mathrm{S_N1}$ or $\mathrm{S_N2}$ for secondary alcohols.Also, alcohols are not good leaving groups also! But after protonation the water is a very good leaving group.
Yes, here itll be $\mathrm{S_N1}$ preferably. Why not $\mathrm{S_N2}$?, one cause is steric crowding in the adjacent carbon and for the attacking nucleophile and leaving group nature comparison see here, More
Actually, secondary alcohols undergoes $\mathrm{S_N1}$ or $\mathrm{S_N2}$ depending upon the substrate you are using. For e.g. In your case(as provided above) the substrate has steric hindrance nearby alcoholic group and the carbocation will be stable due to the migratory aptitude of the methyl group. Hence, here should be $\mathrm{S_N1}$ and you have to see the structure of substrate to decide $\mathrm{S_N1}$ or $\mathrm{S_N2}$ for secondary alcohols. Also, alcohols are not good leaving groups also! But after protonation the water is a very good leaving group.
Actually, secondary alcohols undergoes $\mathrm{S_N1}$ or $\mathrm{S_N2}$ depending upon the substrate you are using. For e.g. In your case(as provided above) the substrate has steric hindrance nearby alcoholic group and the carbocation will be stable due to the migratory aptitude of the methyl group. Hence, here should be $\mathrm{S_N1}$ and you have to see the structure of substrate to decide $\mathrm{S_N1}$ or $\mathrm{S_N2}$ for secondary alcohols.Also, alcohols are not good leaving groups also! But after protonation the water is a very good leaving group.
More
VOTE
VOTE
VOTE