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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

Predict the products of the reactions of the following compounds with:

(1) chromic acid or excess sodium hypochlorite with acetic acid.

(2)PCC or NaOCl (1 equivalent) with TEMPO.

(a)cyclohexanol (b)1-methylcyclohexanol

(c)cyclopentylmethanol (d)cyclohexanone

(e)cyclohexane (f)1-phenylpropan-1-ol

(g)hexan-1-ol (h)acetaldehyde, CH3CHO

The following pseudo-syntheses (guaranteed not to work) exemplify a common conceptual error.

(a)What is the conceptual error implicit in these syntheses?

(b)Propose syntheses that are more likely to succeed.

Contrast the mechanism of the two preceding reactions, the dehydration and condensation of ethanol.

The following reaction involves a starting material with a double bond and a hydroxyl group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

(a) the Cr in chromic acid

(b) the Cl in sodium hypochlorite

(c) the S in the Swern oxidation

(d) the I in the DMP reagent

(e)the carbinol C in the alcohol that is oxidized.
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