Conversion to Alkyl Chlorides by Reaction with HCl: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an S_N1 substitution reaction with HCl gas dissolved in ether to give the corresponding alkyl chloride. Again, the reaction is limited to alcohols that can from stable carbocations.

Conversion to Alkyl Bromides by Reaction with PBr₃: Primary and secondary alcohols react with PBr₃ to form an intermediate phosphite ester which undergoes S_N2 attack by bromide anion to yield the alkyl bromide with inversion of configuration (the stereochemical inversion is simply a result of the S_N2 displacement).

Conversion to Alkyl Chlorides by Reaction with SOCl₂: Primary and secondary alcohols react with SOCl₂ in polar solvents (i.e., pyridine) to form an intermediate sulfite ester which undergoes S_N2 attack by chloride anion to yield the alkyl chloride with inversion of configuration (the stereochemical inversion is simply a result of the S_N2 displacement). If the reaction is performed in a non-polar solvent such as benzene, an unusual S_Ni mechanism occurs involving frontside attack, and yielding retention of stereochemistry. This reaction is unusual, but is often useful if you desire to control the stereochemical course of a synthesis.

Dehydration of Tertiary Alcohols: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an acid-catalyzed E1 elimination reaction to form the corresponding alkene. Again, the reaction is limited to alcohols that can from stable carbocations.

Dehydration of Secondary and Tertiary Alcohols with POCl₃: Secondary and tertiary alcohols react with POCl₃ to form a dichlorophosphate ester, which undergos an E2 elimination reaction to form the corresponding alkene. Since an E2 elimination is occurring, the hydrogen abstracted must be anti- and coplanar with the oxygen on the leaving group (antarafacial).

Oxidation of Alcohols with Pyridinium Chlorochromate: Primary and secondary alcohols are smoothly oxidized by pyridinium chlorochromate (PCC) in CH₂Cl₂ to form aldehydes and ketones, respectively. The PCC oxidation of primary alcohols to give aldehydes is a very useful reaction, since aldehydes are difficult to prepare and are easily over-oxidized to the carboxylic acid.

Oxidation of Alcohols with "Jones Reagent": Primary and secondary alcohols are oxidized by CrO₃/H₂SO₄ (Jones Reagent) to form carboxylic acids and ketones, respectively; sodium dichromate in acetic acid (Na₂Cr₂O₇) can also be used.

Conversion to Silyl Ethers: Alcohols react with chlorotrimethylsilane to form trimethylsilyl ethers which are stable to many reactions which occur in aprotic medium, but can be readily cleaved by reaction with aqueous acid, regenerating the alcohol. This reaction is often utilized to "protect" an alcohol during a synthesis, such as that shown below (in the synthesis shown, the Grignard reagent would react with the acidic proton on the alcohol, destroying the reagent).