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Chapter 11: Q54P (page 589)

Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis.

Short Answer

Expert verified

The compound that is made up of tetrahydrofuran ring with one alcohol group containing CH2 group is tetrahydrofurfuryl alcohol. This compound is used as a solvent and also an intermediate for many organic syntheses.

Step by step solution

01

About tetrahydrofurfuryl alcohol

The compound that is made up of tetrahydrofuran ring with one alcohol group containing CH2 group is tetrahydrofurfuryl alcohol. This compound is used as a solvent and also an intermediate for many organic syntheses.

02

About the reaction

The treatment of tetrahydrofurfuryl alcohol gives dihydropyran on acidification. The ring gets expanded and it becomes a six-membered ring. In addition to this one double bond will be formed at the first carbon from the oxygen atom.

03

About the mechanism

The lone pair of electrons of oxygen present in the alcohol group abstracts a proton from an acid. This results in the removal of water and the formation of a carbocation. It is subjected to an alkyl shift. On treating with water, the dihydropyran will be formed. The mechanism is shown below.

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Most popular questions from this chapter

Classify each reaction as an oxidation, a reduction, or neither.

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(a) The reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion than retention of configuration. Propose a mechanism that accounts for racemization with excess inversion.

(b)Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Propose a mechanism to show how this reaction goes with apparently complete retention of configuration, yet with racemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with in water to give the starting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in the reaction with HBr.)
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