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Dehydration of Alcohol

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Submitted By Juliemher
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Alcohols and alkyl halides are similar because they both contain an electronegative element bonded to a sp3 hybridized carbon atom. However, they are also dissimilar alkyl halides has a leaving group (X-) while alcohols do not. Nucleophilic substitution with ROH as starting material would displace –OH, a strong base and therefore a poor leaving group (McMurry, 2012).
Structure (Smith) The OH group must be first converted into a better leaving group for an alcohol to undergo a nucleophilic substitution or elimination. This can be done by reaction with an acid. The O atom in an alcohol will be protonated with the treatment of an alcohol with a strong acid via acid-base reaction. This transforms the –OH leaving group into H20, a weak base therefore a good leaving group (McMurry, 2012). Most alcohols are prepared industrially by hydration of alkenes. The reverse reaction canbe used in the laboratory to prepare olefins from commercially available alcohols. The reaction is believed to occur in three steps wherein all are readily reversible (Smith, 2011).
Structure(manual)
Acid catalyzed dehydrations usually follows Zaitsev’s rule wherein it yields the more stable alkene as the major product. The reaction is an E1 process and occurs by the three step mechanisms. Unimolecular loss of water to generate a carbocation intermediate and final loss of proton from the neighboring carbon atom happens after the protonation of the alcohol oxygen to complete the process. Tertiary alcohols usually react fastest in an E1 reaction because they lead to stabilized tertiary carbocation intermediates. Secondary alcohols can be made to react, but the conditions are severe (75% H2SO4, 100 degrees celcius) and sensitive molecules do not persist (Wade, 2013). Dehydration is a beta elimination reaction in which the elements of OH and H are removed from the alpha and beta carbons, respectively. It is typically carried out using H2SO4 and other strong acids or phosphorus oxychloride (POCL3) in the presence of an amine base.
Mechanism (smith)
Alcohols carried out with POCL3 in pyridine take place by an E2 mechanism. Direct E2 elimination of water from alcohol does not occur because hydroxide ion is a poor leaving group. However, the –OH group is converted into a dichlorophosphate (-OPOCl2) which is a good leaving group and is readily eliminated on the reaction of POCL3. Pyridine is both the reaction solvent and the base that removes the neighboring proton in E2 elimination step (Solomons)
Mechanism (mcmurry) Possible side reactions may include the polymerization of cyclohexene, substitution of H2SO4, and formation of an ether.
Structure(slide)

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