preview

What Is The Dehydration Of An Alcohol

Good Essays

Introduction An alcohol is composed of a hydroxyl group attached to a saturated carbon atom. Alcohols on a molecular level can be transformed into alkenes. For this reaction to occur, the alcohol must be dehydrated. Alcohols are capable of being transformed under two known reaction mechanisms, E1 and E2. These mechanisms allow for the dehydration of water and the formation of a double bond which is created into a synthesized alkene. The dehydration of an alcohol can occur in one of two ways. The first way is through being acid catalyzed. This reaction occurs when the acid is presented, and interaction is presented between both the acid and the potential leaving group. As known the hydroxy group is unstable, and not a good leaving group, therefore is needed to be protonated for the detachment of the hydroxy group to take place. In base promoted dehydration, the second method of transforming an alcohol to an alkene, is based on the same concept. The leaving group must be turned stable to be able to become a good leaving group. The difference between the two possible reactions is that base promoted is not reversible. It is not able to be reacted with the alkene in the opposite process. In addition, base promoted and E2 elimination reactions are favorable only when the acidic medium is not able to proficiently complete the reaction. In times when the acid is not able to proceed the reaction, there are certain factors that are used that are able to yield desirable products. Issues seen when a molecule is reacted with a strong acid unexpected rearrangement of carbocations can arise. Moreover, double bond migrations can appear sometimes in the presence of strong acids; however, because this is able to occur during hydrogenation, a base can reduce the occurrence of the migration. There are also changes in the stereochemistry that can possibly occur, as well as side reaction materials such as ethers. When these issues are faced, base promoted elimination is a better way for the reaction to be continued. As previously mentioned, acid catalyzed as well as base promoted must be able to create the hydroxy group into a good leaving group by protonation. According to base promoted reactions, the base that is consumed is

Get Access