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Chapter 14: 31Ea (page 447)

Predict the products of the following Diels-Alder reaction:


Short Answer

Expert verified

Diels-Alder reaction was discovered by the German chemists Otto Diels and Kurt-Alder in 1928. Diels-Alder reaction is an important cycloaddition reaction which is stereospecific. It includes a substituted alkene in the form of a dienophile and a conjugated diene. It proceeds via concerted mechanism. Diels alder reaction can be used to generate 6 membered rings since there is a simultaneous construction of two new Carbon-carbon bonds.Stereochemistry of the dienophile is retained.

Step by step solution

01

Diels-Alder reaction

Diels-Alder reaction was discovered by the German chemists Otto Diels and Kurt-Alder in 1928. Diels-Alder reaction is an important cycloaddition reaction which is stereospecific. It includes a substituted alkene in the form of a dienophile and a conjugated diene. It proceeds via concerted mechanism. Diels alder reaction can be used to generate 6 membered rings since there is a simultaneous construction of two new Carbon-carbon bonds.Stereochemistry of the dienophile is retained.

02

Diene and dienophile

Diene is an organic compound which comprises of two conjugated pi bonds (4 pi bonds) while dienophile is a diene loving compound containing 2 pi electrons.

The diene is

Dienophile is

03

Prediction of product

The reaction is stereospecific (single stereoisomer is obtained) .Endo product is formed as a result of Diels-Alder reaction. A substituent on one bridge is endo when it is cis to the larger of the other two bridges.

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Most popular questions from this chapter

Hydrocarbon A, C10H14 , has a UV absorption at λmax=236nmand gives hydrocarbon B, C10H18, on catalytic hydrogenation. Ozonolysis of A, followed by zinc/acetic acid treatment, yields the following diketo dialdehyde:

b)Hydrocarbon A reacts with maleic anhydride to yield a Diels-Alder adduct. Which of your structures for A is correct?

How can you account for the fact that cis-1,3-pentadiene is much less reactive than trans-1,3-pentadiene in Diels-Alder reaction.

Question:βOcimene is a pleasant-smelling hydrocarbon found in the leaves of

certain herbs. It has the molecular formula and a UV absorption

maximum at 232 nm. On hydrogenation with a palladium catalyst,

2,6-dimethyloctane is obtained. Ozonolysis of βOcimene, followed by

treatment with zinc and acetic acid, produces the following four

fragments:

(a)How many double bonds does βocimene have?

(b)Is βocimene conjugated or non-conjugated?

(c)Propose a structure for βocimene.

(d)Write the reactions, showing starting material and products.

Draw a segment of the polymer that might be prepared from 2-phenyl-1,3-butadiene.

If pure vitamin A hasλmax =5 325 (ε= 50,100), what is the vitamin A concentration in a sample whose absorbance at 325 nm is A = 0.735 in a cell with a path length of 1.00 cm?
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