R ether.35°c PB -Br Displac B CH3CH CH3CH2 a phosphite ester Conversion to Alkyl Chlorides by Reaction with SoCl, Primary and secondary alcohols react with SoCl, in polar solvents (i. e, pyridine) to form an intermediate sulfite ester which undergoes S2 attack by chloride anion to yield the alkyl chloride with inversion of configuration(the stereochemical inversion is simply a result of the S,2 displacement). If the reaction is performed in a non-polar solvent such as benzene, an unusual S, i 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 sOCI2 pendine Non-Polar CI/NN2Displacement SNi Displacement with Inversion with Retention a sulfite ester a sulfite este Dehydration of Tertiary Alcohols: Tertiary alcohols, or alcohols which can lose the hydroxyl group to form a stable carbocation, can undergo an acid-catalyzed El elimination reaction to form the corresponding alkene. Again, the reaction is limited to alcohols that can from stable carbocationsConversion 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 SN2 attack by chloride anion to yield the alkyl chloride with inversion of configuration (the stereochemical inversion is simply a result of the SN2 displacement). If the reaction is performed in a non-polar solvent such as benzene, an unusual SNi 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