Substitution (S_N1 & S_N2)

15 reactions in this topic, each with the reagents, the mechanism and the structure of the product.

When treated with acid, ether od tertiary, benzylic, or allilyc carbons can fragment to give a carbocation, which is then trapped

Alkyl halides will react with water to form alcohols through an SN1 mechanism.

Alkyl halides (or tosylates) will react with hydroxides ions to give alcohols. This is an SN2 reaction.

Alkyl halides (or tosylates) will react with Gilman reagents (organocuprates) to form alkanes in SN2 reaction.

Treatment of tertiary alcohols with HCl leads to the formation of tertiary alkyl chlorides.

Tertiary alcohol can be converted to tertiary alkyl iodide with hydroiodic acid (HI).

Amines will react with alkyl halides to give ammonium salts. This reaction is known as Amine (N-)Alkylation.

Alkyl halides (or tosylates) will react with azide ions (such as NaN3 or KN3) in SN2 reaction to give alkyl azides.

Alkyl halides can be converted to ethers when dissolved in alcohol solvents through an SN1 reaction.

Alkyl halides (or tosylates) will react with cyanide ion to give alkyl cyanides (nitriles) in an SN2 reaction.

The 1,2-hydride shifts can occur during the reactions if an unstable carbocations is formed next to a tertiary carbon.

The 1,2-alkyl shift can occur during the substitution reactions if an unstable carbocation is formed adjacent to a quaternary carb

Nucleophilic bimolecular substitution (SN2) is the general reaction for primary and secondary haloalkanes (alkyl halides) where th

Alkyl halides (or tosylates) will react with Gilman reagents (organocuprates) to form alkanes in SN2 reaction.

Alkyl halides (or tosylates) will react with the hydrosulfide ion (HS‾) to give thiols.

Substitution (SN1 & SN2)