Which will be more stable carbocation upon heterolysis of #"C"-"Cl"# bond?

Answer 1

Consider the consequence of the heterolysis you describe for each, in turn,

#(1)#

This would be stabilized by resonance,

#(2)#

The cyclic ether would be acting as an electron donating group, stabilizing the positive charge.

#(3)#

This is stabilized by hyperconjugation to the highest degree (#3°#).

#(4)#

This is a primary carbocation: a very unstable molecule.

As a result of this qualitative analysis, #(1)# and #(3)# are very close in stability, but I would wager #(1)# is slightly more stable. Resonance is a very powerful effect.

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Answer 2

The carbocation formed upon heterolysis of a C-Cl bond will be more stable if the carbon atom bearing the positive charge is more substituted. This means that a tertiary carbocation (where the carbon atom bearing the positive charge is attached to three other carbon atoms) will be more stable than a secondary carbocation, which in turn will be more stable than a primary carbocation. The stability of carbocations follows the order: tertiary > secondary > primary > methyl.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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