Alcohols react with PBr₃ to form an intermediate phosphite ester, which undergoes an S_N2 attack by bromide anion to give the alkyl bromide, with inversion of stereochemistry.

Tert-butoxide in tert-butyl alcohol will induce an elimination in an alkyl halide such as this. Since the compound is a secondary alkyl halide, it is most likely to be an E2 process, which means that the bromine and a trans hydrogen will be lost to form the alkene.

Carboxylate anion is a poor base, but is a decent nucleophile. It will react with the alkyl halide to give a carboxylate ester by an S_N2 mechanism.

Hydroboration of an alkyne, followed by oxidative work-up with alkaline peroxide, will yield the anti-Markovnikov enol (in this case, the OH is not bonded to the benzyl position) which will isomerize to give the corresponding ketone.

Hydroboration of an alkene, followed by oxidative work-up with alkaline peroxide, will yield the anti-Markovnikov alcohol (in this case, the OH is bonded to the secondary carbon). Recall that the addition of OH and H are syn.

SOCl₂ in a non polar solvent such as benzene will follow an S_Ni mechanism to give the alkyl choloride with retention of stereochemistry.

Reaction of an alkene with HBr in the presence of peroxides will yield the anti-Markovnikov alkyl bromide (in this case, the Br is bonded to the secondary carbon).

Tert-butoxide in tert-butyl alcohol will induce an elimination in an alkyl halide such as this. Since the compound is a secondary alkyl halide, it is most likely to be an E2 process, which means that the chlorine and a trans hydrogen will be lost to form the alkene.

Hydration of an alkyne in the presence of Hg⁺⁺ yields the Markovnikov enol, which rearranges to form the corresponding ketone. Here, the benzyl position is the "most stable potential carbocation center".

Primary amines react with alkyl halides to give the corresponding secondary amines by an S_N2 mechanism.

In the presence of Lindar, or a "poisoned" catalyst, reduction of alkynes yields the cis alkene.

Aryl amines react with alkyl halides to give the corresponding substituted amine by an S_N2 mechanism.

Hypobromite adds to an alkene to give a halohydrin, with the hydroxide bound to the "Markovnikov" carbon (the one which would form the most stable carbocation); remember that the overall stereochemistry of addition is trans.

Tert-butoxide in tert-butyl alcohol will induce an elimination in an alkyl halide such as this. Since the compound is a secondary alkyl halide, it is most likely to be an E2 process, which means that the chlorine and a trans hydrogen will be lost to form the alkene.

The reaction of an alkene with mercuric acetate, followed by reductive work-up with BH₄^- gives an alcohol, with the OH bonded to the most stable potential carbocation (Markovnikov addition).

Reduction of an alkyne with Li or Na dissolving in liquid ammonia gives partial reduction to the trans alkene.

Thiolate anions react with alkyl halides by an S_N2 mechanism to give the corresponding sulfide.