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In future chapters, we will encounter carbanionsions in which a carbon atom has

Chapter 1, Problem 1.77

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QUESTION:

In future chapters, we will encounter carbanionsions in which a carbon atom has threebonds and a lone pair of electrons and bears a negative charge. Draw another contribut-ing structure for the allyl anion. Now using cartoon representations, draw the three orbit-als that represent the delocalized p system (look at Figure 1.26 for a hint). Which of thethree orbitals are populated with electrons?

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QUESTION:

In future chapters, we will encounter carbanionsions in which a carbon atom has threebonds and a lone pair of electrons and bears a negative charge. Draw another contribut-ing structure for the allyl anion. Now using cartoon representations, draw the three orbit-als that represent the delocalized p system (look at Figure 1.26 for a hint). Which of thethree orbitals are populated with electrons?

ANSWER:

Key concept

Contributing structure

The individual Lewis structures of a molecule are called resonance structures or contributing structures. So, the contributing structures of a molecule are obtained by moving the electron pairs of an atom towards the other atoms.

Bonding molecular orbital

A bonding molecular orbital (BMO) is a type of molecular orbital that forms when atomic orbitals of two or more atoms overlap and combine to form a chemical bond.

BMOs have lower energy than the individual atomic orbitals and they are characterized by the presence of electrons in the region between the nuclei of the atoms.

Non bonding molecular orbital

A non-bonding molecular orbital (NBMO) is a type of molecular orbital that forms when atomic orbitals of two or more atoms overlap but do not combine to form a chemical bond.

NBMOs have higher energy than the individual atomic orbitals and they are characterized by the presence of electrons in regions that are farther from the nuclei of the atoms than the electrons in the bonding molecular orbitals.

Anti bonding molecular orbitals

An antibonding molecular orbital (ABMO) is a type of molecular orbital that forms when atomic orbitals of two or more atoms overlap but the overlap is destructive in nature, resulting in a higher energy level than the individual atomic orbitals.

Antibonding molecular orbitals are characterized by the presence of electrons in regions that are farther from nuclei of the atoms than the electrons in the bonding molecular orbitals.

The electrons in antibonding orbitals are not involved in chemical bonding, and instead they destabilize the molecule.

Step 1 of 3

We are given the structure of an allyl ion

Now we are asked to draw another contributing structure of allyl ion.

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