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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

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4 (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

(a)octan-1-ol (b)octan-3-ol

(c) 4-hydroxydecanal (d) 1-methylcyclohexan-1,4-diol

To practice working through the early parts of a multistep synthesis, devise syntheses of

(a) pentan-3-one from alcohols containing no more than three carbon atoms.

(b) 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent

(a) butan - 1 - ol 鈫� butanal, CH3CH2CH2CHO

(b) but - 2 - en - 1 - ol 鈫� but - 2 - enoic acid, CH3CH = CHCOOH

(c) butan - 2 - ol 鈫� butan - 2 - one, CH3COCH2CH3

(d) cyclopentanol 鈫� 1 - cyclopentylpropan - 1 - ol (twosteps)

(e) cyclopentyclohexanol 鈫� 2 - methylcyclohexanone (several steps)

(f) 1 - methylcyclohexanol 鈫� 2 - methylcyclohexanone (several steps)

Predict the products of the following reactions.

(a) cyclohexylmethanol + TsCl / pyridine (b) product of (a) + LiAlH4

(c) 1- methylcyclohexanol + H2SO4, heat (d) product of (c) + H2, Pt

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.
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