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Question: Explain the following statement. Although HC≡C-is more stable thanH2C=C-,HC≡C+is less stable than H2C=C+.

Short Answer

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Answer

Among the given carbanions, the HC≡C-is more stable than H2C=C-. Among the given carbocations, H2C=C+the ion is more stable than theHC≡C+ion.

Step by step solution

01

Step-by-Step SolutionStep 1: Stability of the carbanions and carbocations

The carbanion in which the lone pair of electrons on a carbon atom is present in the orbital with a greater s character is most stable.

On the other hand, the carbocation in which the positive charge is due to the vacant orbital with less percentage of s character is most stable.

02

Formal charges

The negatively charged ion in which the carbon atom has a formal negative charge and is bonded to three other atoms or groups.

The positively charged ion in which the carbon atom has a formal positive charge and is bonded to three other atoms or groups.

03

Stability of the given carbanions and carbocations

Among the given carbanions, the HC≡C-is more stable than .

The carbon atom with a negative charge in the HC≡C-ion is sp hybridized and has the hybrid orbitals that have about 50% s character.

In the case ofH2C=C- ion, the carbon atom having the negative charge is hybridized and has about 33.33% character. As a result, theHC≡C- ion is more stable.

Among the given carbocations, therole="math" localid="1648979664760" H2C≡CH+ ion is more stable thanHC≡C+ the ion. This is because in , role="math" localid="1648979670575" H2C≡CH+the carbon atom with a positive charge is sp hybridized, and the p orbital is vacant.

On the other hand, inHC≡C+ ion, the carbon atom is sp hybridized, and the vacant orbital has a 50% s character, making it highly unstable.

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