Solution Found!
Predict the major products of acid-catalyzed dehydration of the following alcohols. (a)
Chapter 7, Problem 7-52(choose chapter or problem)
Predict the major products of acid-catalyzed dehydration of the following alcohols. (a) OH pentan-2-ol (b) l-methylcyclopentanol OH CH3 OH CH3 2-methylcyclohexanol (c) OH 2.2-dimethylpropan-1-ol
Questions & Answers
QUESTION:
Predict the major products of acid-catalyzed dehydration of the following alcohols. (a) OH pentan-2-ol (b) l-methylcyclopentanol OH CH3 OH CH3 2-methylcyclohexanol (c) OH 2.2-dimethylpropan-1-ol
ANSWER:Step 1 of 5
Acid-catalyzed dehydration of alcohols:
Dehydration involves the removal of a water molecule from alcohol.
In the presence of an acid, alcohols are protonated, followed by the removal of a water molecule to form a carbocation. This carbocation is stabilized by the removal of a proton from the adjacent carbon forming an alkene.
In the case of secondary alcohols, protons can be removed from either of the adjacent carbon. In these cases, the major product is determined using the Zaitsev rule. According to this rule, the proton is removed from having the smallest number of hydrogen substituents.