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Chapter 20: 73P (page 1038)

A graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation

Short Answer

Expert verified

When O-fluoro bromobenzene is added to magnesium in tetra hydra furan solution it forms O-fluoro phenyl magnesium bromide. But this compound forms the benzyne intermediate.

Step by step solution

01

Formation of benzyne intermediate

When O-fluoro bromobenzene is added to magnesium in tetra hydra furan solution it forms O-fluoro phenyl magnesium bromide. But this compound forms the benzyne intermediate.

02

Formation of Diels alder adduct

As the solvent contains a small amount of furan, the benzyne undergoes a Diels alder reaction to form the adduct. The reaction mechanism is represented as follows:

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Most popular questions from this chapter

For each compound,

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(h)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

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Question: Suppose you have just synthesized heptanoic acid from heptan-1-ol. The product is contaminated by sodium dichromate, sulfuric acid, heptan-1-ol, and possibly heptanal. Explain how you would use acid-base extractions to purify the heptanoic acid. Use a chart, like that in Figure 20-3, to show where the impurities are at each stage.

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan庐. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin庐 insecticide.

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (鈥淓t鈥� is the abbreviation for ethyl.
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