Radical Stability Flashcards
(16 cards)
Allylic
1 unit away from double bond
A-away
Vinyllic
On double bond
Neither
Not on anything relevant
Phenyllic
On double bond on benzene ring
Think of phenol. OH is directly attached to ring.
Benzyllic
One unit away from benzene ring
Order of stability of radicals
Allylic/benzyllic, neither, vinyllic/ phenyllic
3 prime, 2 prime, 1 prime
Formal charge
Valence electrons -lone electrons- bonds
How can the importance of two equally stable molecules be determined?
Based on abundance. More Hs to break off = more abundant.
Order of Stability of cations (+)
Benzyllic, allylic, [3 prime neither, 1 allylic ], neither, vinyllic
Steps of radical reactions
1) initiation
2) propagation
3) termination
Relative yields of Cl
3prime = 5.2
2 prime= 3.9
1prime = 1
How does the C-H bong length relate to stability?
They have an inverse relationship
Looking at relative stability of isomers, what does the structure of the molecule tell you?
More branched = more stable
Due to more 1 prime Cs being present
1 prime bonds are shorter and stronger
Relative boiling points
Amounts of IMFs and/ or types of IMFs determine BP. More branches = higher BP
Higher #s present = higher BP
Hydrogen bonding = higher BP
Bond strength is the ———— of stability!
Opposite
On benzene, Is a radical on a double bond (vinyllic) more stable than one on a single bond?
No!
Vinyllic radicals are the least stable
Stability order: allylic > on a single bond > vinyllic
