Organic Reaction Mechanism
→ refers to the overall description of how a reaction occurs → account for all reactants used and all products formed → how the covalent bonds are broken and formed as well as how electrons are distributed during the chemical reaction
Double-barbed arrow
shows the motion of two electrons
Single-barbed arrow
shows the motion of one electron
Symmetrical bond breaking
→ also called as “homolytic bond cleavage
Symmetrical bond breaking
two electrons are distributed equally to each of the product fragment
Unsymmetrical bond breaking
also called as “heterolytic bond cleavage
Unsymmetrical bond breaking
the two shared electrons go to only one of the two product fragments
Radical reaction
symmetrical bond making and bond breaking
Polar reaction
unsymmetrical bond making and bond breaking
Homolytic cleavage
requires a large input of energy supplied by heat (∆) or light (hv)
Addition to a pi bond
a radical adds to a π bond, thereby destroying the π bond and generating a new radical
Hydrogen abstraction
a radical can abstract a hydrogen atom from a compound, generating a new radical
Halogen abstraction
a radical can abstract a halogen atom, generating a new radical
Ellimination
a double bond forms between the alpha (α) and beta (β) positions
Coupling
two radicals join together and form a bond
Initiation
is when the radicals are created
Propagation
the location of the unpaired electron is moved from place to place
Termination
- is when two radicals annihilate each other by forming a bond
Unsymmetrical cleavage
due to the differences in electronegativity of the bonded atoms
Polar reactions
→ the most common reactions in organic chemistry → see more of the full-headed ( ) or double- barbed arrow notation
0.5 to 1.7
polar electronegativity
Induction
The withdrawal of electrons towards oxygen is called
Sigma -
atoms are electron-rich atom and prefer to give electron
Sigma +
atoms are electron-poor atom and prefer to accept electron
Nucleophile
δ- atom will be at the tail since it is electron-rich.
Electrophile
δ+ atoms will be at the head ( ) since it is electron-poor. of the full-headed arrow