Dehydration Reaction Practice Problems
The following reaction shows acid-catalyzed dehydration of an alcohol. Indicate how could the equilibrium of this reaction be shifted to the right.
The following reaction shows acid-catalyzed dehydration of an alcohol. Indicate how can the equilibrium of this reaction be shifted to the left.
Predict the structure of the alcohol that would yield the following alkene without rearrangement.
When HCl was used to perform the dehydration reaction of an alcohol, the desired product was not formed. Identify the product that was actually formed in this reaction.
Identify the alcohol that can be dehydrated to form the following alkene through carbocation rearrangement.
Identify the alcohol that can be dehydrated to form the following alkene without carbocation rearrangement.
Give the major products formed by dehydration of the given alcohols through sulfuric acid.
Show the products of the following acid-catalyzed dehydration reactions. Also, label them as major and minor.
When the following compound is heated in presence of H2SO4, what constitutional isomer is formed as the major product? Indicate whether the product has any stereoisomers.
Draw the structure of the major product obtained when the given compound is heated with H2SO4.
When 3,3,5-trimethyl-2-hexanol and 2,3,5-trimethyl-2-hexanol are heated with H 2SO4, they both undergo dehydration to produce 2,3,5-trimethyl-2-hexene. Which of the two alcohols dehydrates faster?
Three alkenes are produced when the following seven-membered ring alcohol is dehydrated. Propose a mechanism to explain how they are formed.
In the acid-catalyzed dehydration of 1-heptanol to 2-heptene, determine the stereoisomers formed and which of them would be the major product.
The dehydration of alcohols by acids is reversible, while the dehydrohalogenation of alkyl halides by bases is irreversible. Elucidate.
Propose the major products expected from the sulfuric acid-catalyzed dehydration reactions of the following alcohols. Also. draw a mechanism to show the product formation.
Provide a suitable mechanism for the formation of major products in the following reaction.
E1 elimination reactions of alkyl halides usually give a mixture of substitution and elimination products which is why these are not commonly used for synthetic purposes.
On the other hand, the sulfuric acid-catalyzed dehydration of cyclopentanol gives a good yield of cyclopentene although it follows the same E1 mechanism. Explain why this reaction does not give substitution products.