Lecture 5: Organic Reaction Mechanisms

Outline:

 Substitution
 Elimination
 Addition
 Bond breaking and bond formation
 Reactive intermediates
 Nucleophiles and Electrophiles
C. Addition Reactions
Kinds of Organic Reactions  An atom or a group of atoms is added
 A multiple bond is broken (usually a double bond)
A. Substitution Reactions
 An atom or a group of atoms is replaced by another
atom or group of atoms

Exercise: Classify each of the following as substitution, elimination

or addition.

B. Elimination Reactions
 An atom or a group of atoms is removed
 Formation of multiple bond (usually a double bond)

Lecture 5: Organic Reaction Mechanisms

 Concerted reactions
o One-step reactions
o A→B
 Stepwise reactions
o Substrate (reactant) is first converted to an
unstable intermediate (reactive intermediate)
o A → reactive intermediate → B
Bond Breaking and Bond Forming

 Reaction mechanism – detailed description of how bonds  Bond Cleavage

are broken and formed in a chemical reaction  Homolytic cleavage
o Electrons are divided usually between
the atoms in the bond after bond
breaking
o Forms uncharged intermediates with
unpaired electrons
 Heterolytic cleavage
o Electrons are divided unequally
between the atoms in the bond after
bond breaking
o Forms charged intermediates
(carbocation or cabanion)
Lecture 5: Organic Reaction Mechanisms

Reactive intermediates  Carbanions

o Unstable intermediates with a negatively charged
 Radicals
carbon
o Unstable intermediates with one unpaired electron

Nucleophiles and Electrophiles

 Carbocations
o Unstable intermediates with a positively charged  Nucleophile
carbon o A nucleophilic center is an electron-rich atom that is
capable of donating a pair of electrons.
o Any negative ion or uncharged molecule with an
unshared electron pair is a potential nucleophile.
o Lewis base
Lecture 5: Organic Reaction Mechanisms

 Electrophile
o An electrophilic center is an electron-deficient atom that is
capable of accepting a pair of electrons.
o Lewis acid

Exercise:

o Identify all of the nucleophilic centers in each of the

following compounds

o Identify all of the electrophilic centers in each of the

following compounds