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Chapter 16: PROBLEM 16.52 (page 637)

Question: Compounds containing triple bonds are also Diels–Alder dienophiles. With this in mind, draw the products of each reaction.

a.

b.

Short Answer

Expert verified

a.

Product of a.

b.

Product of b.

Step by step solution

01

Arrangement of diene and dienophile

The diene and the triple bonded species are placed in the same manner as the diene and dienophile for the Diels-Alder reaction.

02

Triple bond in dienophile

The triple bond also behaves as the dienophiles in the Diels-Alder reaction. On undergoing the said reaction, the double bond is left after the cleavage of one bond of the dienophile

03

Diene and dienophile for the given products

a. The structures are re-drawn, and the bonds are cleaved in the represented manner to form a six-membered ring.

Product of a.

b. The structures are re-drawn, and the bonds are cleaved in the represented manner to form a six-membered ring.

Product of b.

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Most popular questions from this chapter

Question: a. Draw resonance structures for the carbocation formed after loss of a leaving group from phytyl diphosphate. b. Draw the two-step mechanism for Friedel–Crafts alkylation of 1,2-dihydroxynaphthoic acid with this carbocation to form X.

Question: Use resonance theory and the Hammond postulate to explain why 3-chloroprop-1-eneCH2=CHCH2Cl is more reactive than 1-chloropropaneCH3CH2CH2Cl in SN1 reactions.

Question: A transannular Diels–Alder reaction is an intramolecular reaction that occurs when the diene and dienophile are contained in one ring, resulting in the formation of a tricyclic ring system. Draw the product formed when the following triene undergoes a transannular Diels–Alder reaction.

Question: The major product formed by addition of HBr to CH32C=CH-CH=CCH32 is the same at low and high temperature. Draw the structure of the major product and explain why the kinetic and thermodynamic products are the same in this reaction

Question: The treatment of isoprene CH2=CCH3CH=CH2 with one equivalent of mCPBA forms A as the major product. A gives a molecular ion at 84 in its mass spectrum, and peaks at 2850–3150 cm-1in its IR spectrum. The 1H NMR spectrum of A is given below. What is the structure of A?
See all solutions

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