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Chapter 11: Q57P (page 590)

Show how you would synthesize the following compound. As starting materials, you may use any alcohols containing five or fewer carbon atoms and any necessary solvents and inorganic reagents.

Short Answer

Expert verified

A three-membered ring that bears one oxygen atom in the place of carbon or a cyclic ether are called epoxides. This compound is more reactive when compred with acyclic ether because of the strain of the ring.

Step by step solution

01

About epoxides

A three-membered ring that bears one oxygen atom in the place of carbon or a cyclic ether are called epoxides. This compound is more reactive when compred with acyclic ether because of the strain of the ring.

02

About the given compound

The given compound contains epoxide ring. To this ring cyclopentane is attached. Also a cyclobutane and a butane also attached. The IUPAC name for this compound is 2-butyl-2-cyclobutyl-1-oxaspiro[2.4]heptane.

03

About the synthesis

The synthesis can be carried out by dividing the given compound into various fragments. The fragments are shown below.

Fragments of the compound

The reaction is carried out using simple reagents. The reaction scheme is shown below.

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Most popular questions from this chapter

Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa= -2.6) is a much stronger acid than acetic acid (CH3COOH,pKa =4.8)

Give the structures of the products you would expect when each alcohol reacts with

(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.

(a) butan-1-ol (b) 2-methylbutan-2-ol

(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol

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

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

When cis-2-methylcyclohexanol reacts with the Lucas reagent, the major product is 1-chloro-1-methylcyclohexane. Propose a mechanism to explain the formation of this product.
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