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Addition Reactions and Their Mechanisms

Here are the classifications for the reactions: 1. CH3CH=CH2 + HBr → CH3CHBrCH3 Addition 2. CH3CH2CH2Br → CH3CH=CH2 + HBr Elimination 3. CH3CH2Cl + NaOH → CH3CH2OH + NaCl Substitution 4. CH3CH(Br)CH3 → (CH3)2C=CH2 Rearrangement

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671 views47 pages

Addition Reactions and Their Mechanisms

Here are the classifications for the reactions: 1. CH3CH=CH2 + HBr → CH3CHBrCH3 Addition 2. CH3CH2CH2Br → CH3CH=CH2 + HBr Elimination 3. CH3CH2Cl + NaOH → CH3CH2OH + NaCl Substitution 4. CH3CH(Br)CH3 → (CH3)2C=CH2 Rearrangement

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General Types of

Organic Reactions
and their Mechanisms

Addition Reactions
Objectives
• 1. distinguish the general types of
organic reaction from given
chemical equations
• 2. illustrate the types of reactions
through examples
• 3. explain the mechanism of each
general type of organic reaction
Organic Reaction Mechanism
Mechanism
Nucleophilie
Electrophiles
Types of Organic Reactions
• Organic reactions can be categorized into
several basic types.
• Some reactions fit into more one category.
• Example, some substitution reactions
follow an addition-elimination pathway.
• This overview isn’t intended to include every
single organic reaction, Rather, it is intended to
cover the basic reactions
Types of Reactions
• Addition Reactions
• Substitution Reactions
• Elimination Reactions
• Rearrangement Reactions
• Organic Redox Reactions
Organic Reactions and
Mechanisms
• Organic reactions are the chemical
reactions that are undergone by organic
compounds (the chemical compounds
containing carbon)
• The four main reaction classes
1. Additions
2. Eliminations
3. Substitutions, and
4. Rearrangements.
Four Main Types of
Organic Reactions
• Addition Reaction- the components A and
B are added to the carbon-carbon multiple
bonds and this is called addition reaction
Four main Reaction Classes
• Although a multiple bond is stronger than a single bond, the π bonds of
the multiple bond are weaker than the σ bond.
• The high electron density located between multiply bonded carbon
atoms, however, causes alkenes and alkynes to behave like
nucleophiles, where nucleophilic attack occurs from the more weakly
bound π electrons.
• Hence alkenes and alkynes are regarded as functional groups.
Nucleophilic attack occurs on the Hδ+ atom of the polar HCl bond,
initially producing a species with a carbon that has only three bonds, a
carbocation. In a second nucleophilic attack, Cl−, the electrophile in ,
attacks the carbocation:

CH2=CH2 + HCl CH3CH2Cl


Four main Reaction Classes
• Elimination Reaction - reactions which involve
the elimination or removal of the adjacent atoms. After
these multiple bonds are formed and there is a release of
small molecules as products.
CH3CH2Cl → CH2=CH2 + HCl

https://saylordotorg.github.io/text_general-chemistry-principles-patterns-and-applications-v1.0/s28-04-
common-classes-of-organic-reac.html
Four main Reaction Classes
• Substitution Reaction- are characterized by
replacement of an atom or group (Y) by another atom or
group (Z). Aside from these groups, the number of
bonds does not change.

• Rearrangement Reaction - generates an


isomer, and again the number of bonds normally does
not change.
Types of Reactions
ADDITION REACTION
Electrophilic Addition
Addition Reactions – Electrophilic Addition
Addition Reactions – Electrophilic Addition
Nucleophilic Addition
to carbon-carbon double bonds
Addition Reactions of Alkenes
• Because both electrophile and nucleophile add to the
double bond, the electrophile is the first species that adds,
this characteristic reaction of alkenes is called electrophilic
addition reaction.
reaction

• This reactivity makes alkenes an important class of organic


compounds because they can be used to synthesize a wide
variety of other compounds.
• The particular product obtained depends only on the
electrophile and the nucleophile used in the addition reaction.
Addition Reactions of
Alkenes
Addition of a Hydrogen Halide to an Alkene
Addition Reactions of
Alkenes
Addition of HCl to 2-methyl propene
Addition Reactions of
Alkenes
Addition of HCl to 2-methyl propene
Addition Reactions of
Alkenes
 CARBOCATION STABILITY
 Carbocations are classified according to the number of alkyl
substituents that are bonded to the positively charged carbon.
 Primary carbocation – has one alkyl substituent.
 Secondary carbocation – has two alkyl substituents.
 Tertiary carbocation – has three alkyl substituents.
 The stability of a carbocation increases as the number of alkyl
substituents bonded to the positively charged carbon
increases.
 Thus, the tertiary carbocations are more stable than
secondary, and secondary carbocations are more stable than
primary carbocation
Addition Reactions of
Alkenes
 CARBOCATION STABILITY

 The reason for this pattern of stability is that alkyl groups


bonded to the positively carbon decrease the
concentration of positively charge on the carbon since
they can donate electrons through the σ bond better than
hydrogen can; decreasing the concentration of positive
charge makes the carbocation more stable.
stable
Electrophilic Addition Reaction

• A reagent which can accept an electron


pair in a reaction
Electrophilic Addition Reaction
• The major product obtained from the addition of HI to 2-
methyl-2-butene is 2-iodo-2-methylbutane

• The major product obtained from the addition of HBr to 1-


methylcyclohexane is 1-bromo-1methylcyclohexane.

• In both cases, more stable tertiary carbocation is formed


more rapidly.
Addition of Water to an Alkene
CH3CH=CH2 + H2O no reaction
 If an acid is added to the solution (the acid most
often used is H2SO4), then the outcome is much
different: a reaction will occur because the acid
provides an electrophile (H+). The product of the
reaction is an alcohol. The addition of water(H2O) to
a molecule is called hydration, so the alkene will be
hydrated in the presence of water and acid.
Addition of Water to an Alkene
• The acid is a catalyst- it increases the rate at which a
product is formed, but it does not affect the amount of
product formed. Because the catalyst in the hydration of
an alkene is an acid, hydration is an acid- catalyzed
reaction
 Notice that the first two steps of the mechanism for the acid-
catalyzed addition of water to an alkene are essentially the same
as the two steps of the mechanism for the addition of hydrogen
halide to an alkene:
Addition of Alcohol to an
Alkene
Addition Reactions – Electrophilic Addition
Addition Reactions – Electrophilic Addition
Nucleophilic Addition
Nucleophilic Addition
Nucleophilic Addition
to carbon-hetero double bonds
Nucleophilic Addition
to carbon-hetero double bonds
Carbonyl
Nitriles
Imines and other
Check your Understanding
1. Write down the mechanism for the following reaction
and predict which of the two possible products will
be formed in the greatest yield. Write down the
structures of the two possible products and explain
your answer.
• CH3 CH CH2 + HBr

2. What Alkene would be used to synthesize 3-


bromohexane?

___?______ + HBr CH3CH2CHCH2CH2CH3


Br
Check your Understanding
Check Your Understanding
• Classify each reaction as addition,
elimination, substitution, or
rearrangement.

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