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Chapter 16: PROBLEM 16.75 (page 640)

Question: Devise a stepwise mechanism for the conversion of M to N. N has been converted in several steps to lysergic acid, a naturally occurring precursor of the hallucinogen LSD (Figure 18.4).

Short Answer

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Answer

Step by step solution

01

Retro Diels-Alder reaction

The retro Diels-Alder product may undergo ring-opening.

The driving force for the retro Diels-Alder product is the formation of another product by the cycloaddition or relaxation of the strained product.

02

Explanation

Compound M undergoes ring opening via the retro Diels Alder reaction and further undergoes intramolecular Diels-Alder reaction.

The reaction scheme is shown below:

Retro Diels-Alder product

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Most popular questions from this chapter

Question: Devise a synthesis of X from the given starting materials. You may use any organic or inorganic reagents. Account for the stereochemistry observed in X.

Question: Why is the bond dissociation energy for the C-C bond in ethane much higher than the bond dissociation energy for the labeled C-C in but-1-ene?

Question: Addition of HBr to alleneCH2=C=CH2forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.

Question: Diels–Alder reaction of a monosubstituteddiene (such as CH2=CH-CH=CHOCH3) with a monosubstituteddienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.

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

a.

b.
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