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Chapter 17: Q.13. (page 641)

Question: (a) How is each N atom in quinine, an effective antimalarial drug that reduces fever, hybridized? (b) In what type of orbital does the lone pair on each N reside?

Short Answer

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Answer


a. Hybridization of each N atom is as follows:

At 1: sp3hybridized

At 2: sp2hybridized

b. The lone pair resides in the following position:

At 1: sp3hybrid orbital

At 2: sp2 hybrid orbital

Step by step solution

01

Lone pair

The heterocycles have at least one pair of non-bonding electrons, i.e., lone pairs.

Depending upon the type of bond, these lone pairs can be part of aromatic rings and will be involved in delocalization or cannot be involved in delocalization.

02

 Step 2: Hybridization and orbitals

Quinine

At 1: N atom is attached to four groups (three atoms and one lone pair).Therefore, it is sp3 hybridized. The lone pair is not involved in delocalization and resides in asp3 hybrid orbital.

At 2: N atom is attached to three groups (two atoms and one lone pair).Therefore, it is sp2hybridized. The lone pair is not part of the aromatic ring and resides in a sp2hybrid orbital.

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Most popular questions from this chapter

Question: Methotrexate, a drug that inhibits the metabolism of folic acid, is used in the treatment of a variety of cancers and autoimmune disorders such as rheumatoid arthritis. (a) Give the hybridization of each N atom in methotrexate. (b) In what type of orbital does the lone pair of each N reside? (c) Explain why the bicyclic ring system that contains four N atoms is aromatic.

Question: Use the inscribed polygon method to show the pattern of molecular orbitals in cyclooctatetraene.

a. Label the MOs as bonding, antibonding, or nonbonding.

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[A] C13NMR signals: 16, 29, 125, 127.5, 128.4, and 144 ppm

[B] C13 NMR signals: 15, 26, 126, 128, and 142 ppm

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