Orgo destroyer #137

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akimhaneul

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Which compound reacts fastest in an sn1 type of reaction?

Isn't D pretty destabilizing since its not aromatic? Why does answer key says it's fair?

@Orgoman22

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Which compound reacts fastest in an sn1 type of reaction?

Isn't D pretty destabilizing since its not aromatic? Why does answer key says it's fair?

@Orgoman22

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D is a non aromatic compound, which is different than an anti-aromatic compound. Anti-aromatic compounds (like c) are very unstable. This means that it would require too much energy to produce a carbocation and would be bad.

D is non aromatic, like A. D is probably even better than A due to resonance stabilizing the positive charge.
 
D is a non aromatic compound, which is different than an anti-aromatic compound. Anti-aromatic compounds (like c) are very unstable. This means that it would require too much energy to produce a carbocation and would be bad.

D is non aromatic, like A. D is probably even better than A due to resonance stabilizing the positive charge.

Why is D nonaromatic?


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Why is D nonaromatic?


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Take a look at the carbon on the bottom (opposite of the positive charge in your drawing). This carbon is bonded to 4 other atoms: 2 carbons and 2 hydrogens. This means that the atom has sp3 hybridized orbital. Aromatic and Anti-aromatic compounds need to be a complete system of p orbitals, but since this carbon atom does not have p orbitals it cannot be aromatic.

Another way to look at it is to try and take the positive charge around the whole atom via resonance without being stopped. If you cannot, then you do not have an aromatic or an anti-aromatic. It is impossible to put the positive past that bottom carbon.

(The pic is not the best, but I'm not to familiar with the software I used to make it lol)
 

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Which compound reacts fastest in an sn1 type of reaction?

Isn't D pretty destabilizing since its not aromatic? Why does answer key says it's fair?

@Orgoman22

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No......This molecule is fairly stable.....Non aromatic is fine.......ONLY when you get a specie that is Anti-Aromatic do we call it the KISS of DEATH !!! For example, if 2.chloro -1, 3-cyclopentadiene reacted in an SN1 reaction, we would get an Anti-Aromatic specie that would be horribly unstable. The molecule pictured above is decent since it is a secondary carbocation with resonance. However, it is not nearly as stable as a specie that is aromatic !

Hope this helps.

Dr. romano
 
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