A. Only a small amount (less than 0.01%) of the enol form of diethyl malonate is present at equilibrium. Write a structural form
ula for this enol.
b. Enol forms are present to the extent of about 8% in ethyl acetoacetate. There are three constitutionally isomeric enols possible. Write structural formulas for these three enols. Which one do you think is the most stable? The least stable? Why?
c. Bromine reacts rapidly with both diethyl malonate and ethyl acetoacetate. The reaction is acid-catalyzed and liberates hydrogen bromide. What is the product formed in each reaction?
b. Enol forms are present to the extent of about 8% in ethyl acetoacetate. There are three constitutionally isomeric enols possible. Write structural formulas for these three enols. Which one do you think is the most stable? The least stable? Why?
c. Bromine reacts rapidly with both diethyl malonate and ethyl acetoacetate. The reaction is acid-catalyzed and liberates hydrogen bromide. What is the product formed in each reaction?
1 answer:
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Answer:
The mechanism is E1 and the product is cyclohexene
Explanation:
Attached to this answer is an image of the reaction mechanism of the reaction between cyclohexanol and concentrated sulfuric acid/phosphoric acid. The acid (H3O^+) acts as catalyst.
We can see that the first step in the mechanism is the protonation of the -OH group of the alcohol. This is followed by loss of water molecule which is a good leaving group.
The water now acts as a Lewis base by abstracting a proton from the substrate, forming cyclohexene and regenerating the acid catalyst.
