Why is triphenylmethyl radical so stable?
The stability of radicals can also be increased by aromatic substituents at the radical carbon atom. The central radical carbon atom of the triphenylmethyl radical, for instance, carries three phenyl groups. Therefore, the radical is highly resonance-stabilized.
How will you explain the stability of triphenylmethyl cation?
Triphenylmethyl cation is very stable because +ve charge of methyl carbon is delocalized in three phenyl rings. In each phenyl ring, +ve charge is developed on 2 ortho position and para position. i.e. three resonating structures. Total resonating structures given by triphenylmethyl cation are nine.
Why triphenylmethyl carbocation is more stable than benzyl Carbocation?
The benzyl cation has four resonance contributors: one on the exocyclic carbon and three in the ring. The second aromatic ring provides three more resonance contributors, so there are now seven resonance structures.. The triphenylmethyl cation has ten resonance contributors, so it is the most stable carbocation.
Is phenyl radical stable?
For that reason alkyl radicals (generally considered to be sp2 hybridized) are the most stable, followed by vinyl and phenyl radicals (sp-hybridized) , followed by alkynyl radicals.
Why is tropylium cation more stable than Triphenylmethyl carbocation?
The tropylium cation is more stable than triphenylmethyl carbocation. This is so because tropylium cation is the aromatic compound. Explanation: The aromatic compound is defined as the compounds that obey the Huckel’s rule.
What is the order of stability of carbocation?
Thus the observed order of stability for carbocations is as follows: tertiary > secondary > primary > methyl.
How many resonance structures does the triphenylmethyl carbocation have?
The triphenylmethyl cation has ten resonance contributors, so it is the most stable carbocation.
What is phenyl carbocation?
The phenyl cation is an unstable, high-energy species. Because of the high bond energy of the aromatic C−H bond, the phenyl carbocation is unstable. Note: Because the phenyl cation core has two ligands but no lone pairs, sp is the most stable hybridization.
Why is phenyl carbocation unstable?
The phenyl carbocation is unstable because of the high bond energy of the aromatic C-H bond.
Why is phenyl radical unstable?
The phenyl cation is an unstable, high-energy species. Because of the high bond energy of the aromatic $C – H$ bond, the phenyl carbocation is unstable. Note: Because the phenyl cation core has two ligands but no lone pairs, $sp$ is the most stable hybridization.
Why is Tropylium carbocation more stable?
Coming to the point ,tropylium cation is most stable of the cations you have listed because of extended conjugation and resonance . Tropylium cation is more stable than benzyl cation simply because it has seven resonating structures while benzyl cation has five. More the resonating structures , more the stability.
Why is Tricyclopropyl carbocation more stable than Triphenylmethyl carbocation?
Cyclopropyl methyl carbocation has dancing resonance (informal name) , and since it is a kind of resonance so its more stable than trimethyl mythyl cabocation which has only hyper. tri cyclopropyl methyl carbocation is the most stable carbocation.
What is the difference between triphenyl methyl carbocation and tricyclopropyl methyl carbocation?
The Tricyclopropyl methyl carbocation is greatly benefited by angle strain. The bent bond effect greatly stabilizes the cation by providing a large pseudo – pi system that involves the electrons of the “bent bonds” of the cyclopropyl rings Conversely, the Triphenyl methyl carbocation suffers form steric strain.
What is the lifetime of the triphenylmethyl radical?
Mesomeric forms of the triphenylmethyl radical Lifetime for the triphenylmethyl radical Radicals are often intermediates of reactions and their lifetime is generally very short [4]. They can be destroyed in different ways :
Which is the most stable carbocation?
The triphenylmethyl cation has ten resonance contributors, so it is the most stable carbocation.
Why are trityl carbocations so stable?
The trityl carbocation created is very stable because the positive charge can be delocalized over all three rings through ten different resonance structures placing the (+) charge on the circled atom.