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Chapter 25: 78 (page 1048)

Heating compound X with aqueous formaldehyde forms Y C17H23NO, which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska (Section 25.10). Identify Y and explain how it is formed.

Short Answer

Expert verified

The reaction involving the delocalization of pi-electrons within a compound from an electron-deficient site to an electron-rich site is known as the intramolecular electron transfer reaction.

In the given compound, the pi-electrons are delocalized as the lone pair of electrons on the nitrogen atom of the amine attacks the electrophilic carbon forming a C-N bond. The electron-rich carbon attacks the electrophilic carbonyl carbon, forming a new C-C bond.

Intramolecular electron transfer in the substrate

Step by step solution

01

Intramolecular electron transfer 

The reaction involving the delocalization of pi-electrons within a compound from an electron-deficient site to an electron-rich site is known as the intramolecular electron transfer reaction.

In the given compound, the pi-electrons are delocalized as the lone pair of electrons on the nitrogen atom of the amine attacks the electrophilic carbon forming a C-N bond. The electron-rich carbon attacks the electrophilic carbonyl carbon, forming a new C-C bond.

Intramolecular electron transfer in the substrate

02

Dehydration

The protonated amino group is stabilized as a molecule of it is lost when the lone pair of electrons on the nitrogen atom attacks the electrophilic carbon, resulting in ring closure.

Ring closure

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Most popular questions from this chapter

Question: What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?

Explain the observed difference in the pKa values of the conjugate acids of amines A and B.

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