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Chapter 24: Q.4. (page 962)

Question: Acid-catalyzed dehydration of β-hydroxy carbonyl compounds occurs by the mechanism discussed in Section 9.8. With this in mind, draw a stepwise mechanism for the following reaction.

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01

Dehydration reaction

The reverse of the dehydration reaction is hydration reaction. Hydration means addition of water, whereas dehydration means removal of water.

Alkene is formed in dehydration of alcohol, while alcohol is formed in hydration of alkene.

02

Mechanism of the reaction

In the first step of the reaction, oxygen of hydroxyl group abstracts a proton from acid following removing of water to form carbocation.

In the next step, the hydrogen sulfate ion abstracts the alpha hydrogen and results in the formation of (E)-but-2-enal.

The mechanism is shown below:

Mechanism of the reaction

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Most popular questions from this chapter

Question: Which carbonyl compounds do not undergo an aldol reaction when treated with OH- in H2O ?

Question:Even though B contains three ester groups, a single Dieckmann product results when B is treated with NaOCH3in CH3OH, followed by H3O+. Draw the structure and explain why it is the only product formed.

Question: What unsaturated carbonyl compound is formed by dehydration of each β-hydroxy carbonyl compound?

Question: Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.

Question: Draw the products formed in each crossed aldol reaction.

a.

b.
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