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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

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

(a)chromic acid

(b)PCC(pyridinium chlorochromate)

(c)sodium hypochlorite/ acetic acid

(d)DMSO and oxalyl chloride

(e)DMP(periodinane)reagent

Under normal circumstances, tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it can undergo a migration of the double bond (called an allylic shift) and subsequent oxidation of the alcohol. A particularly effective reagent for this reaction is Bobbitt鈥檚 reagent, similar to TEMPO used in many oxidations. (M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)

Show the expected product when each of these 3掳 allylic alcohols is oxidized by Bobbitt鈥檚 reagent.

(a)

(b)

(c)

(d)

Chromic acid oxidation of alcohol (Section 11-2A) occurs in two steps: formation of the chromate ester, followed by an elimination of chromium. Which step do you expect to be rate-limiting? Careful kinetic studies have shown that Compound A undergoes chromic acid oxidation over 10 times as fast as Compound B. Explain this large difference in rates.

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)
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