Orgo destroyer #137

Started by akimhaneul
This forum made possible through the generous support of SDN members, donors, and sponsors. Thank you.
Get help with your application

Use all the free resources available to you from SDN: articles, guides, expert advising, forums discussions, and school research.

Browse articles Compare schools My application plan Read Interview Feedback
Practice for interviews Ask an Advisor
A

akimhaneul

Full Member
7+ Year Member
Advertisement - Members don't see this ad
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

ImageUploadedBySDN1477357847.900595.jpg



Sent from my iPhone using SDN mobile
 
Sort by date Sort by votes
akimhaneul said:
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

View attachment 210183


Sent from my iPhone using SDN mobile
Click to expand...
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.
 
Upvote 0 Downvote
Crithu said:
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.
Click to expand...

Why is D nonaromatic?


Sent from my iPhone using SDN mobile
 
Upvote 0 Downvote
akimhaneul said:
Why is D nonaromatic?


Sent from my iPhone using SDN mobile
Click to expand...
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)
 

Attachments

  • cyclohexene.png
    cyclohexene.png
    12.4 KB · Views: 149
Upvote 0 Downvote
akimhaneul said:
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

View attachment 210183


Sent from my iPhone using SDN mobile
Click to expand...
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
 
Upvote 0 Downvote
You must log in or register to reply here.