Reactions of Alkyl Halides - II
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry and stereochemistry of the reaction.Click the mouse on the reactant molecule to view the answer;
click on the reagent to briefly review the reaction.
PBr3 reacts with alcohols to give alkyl bromides. The reaction involves an intermediate phosphite ester and proceeds with inversion of stereochemistry.
The tertiary tosylate will decompose in the polar solvent to give the tertiary carbocation. There will be competing reaction from the solvent, to give the ethyl ether, and the more nucleophilic amine, to give the secondary amine.
SOCl2 in a non-polar solvent reacts with alcohols by first forming a sulfite ester, which undergoes an SNi mechanism which proceeds with frontside attack and retention of stereochemistry.
NBS in CCl4 results in allylic bromination. There are three allylic positions in this molecule, and a mixture of products will be observed.
PBr3 reacts with alcohols to give alkyl bromides. The reaction involves an intermediate phosphite ester and proceeds with inversion of stereochemistry.
The tertiary tosylate will decompose in the polar solvent to give the tertiary carbocation. There will be competing reaction from the solvent, to give the ethyl ether, and the more nucleophilic amine, to give the secondary amine.
SOCl2 in a non-polar solvent reacts with alcohols by first forming a sulfite ester, which undergoes an SNi mechanism which proceeds with frontside attack and retention of stereochemistry.
NBS in CCl4 results in allylic bromination. There are three allylic positions in this molecule, and a mixture of products will be observed.