ORGANIC REACTIONS

• Differentiate the roles of nucleophiles and

electrophiles in organic reactions.
• Illustrate the different types of organic reactions:
Addition, Substitution, Elimination, Hydrolysis,
and Condensation by writing chemical reactions.
 Organic Reactions

• Reactions are at the heart of Organic Chemistry.

• Virtually all chemical reactions are woven together by a
few basic themes.
• Begin by looking for electron-rich or deficient sites
at functional groups in the reacting molecules.
• These are often the location of bonds that might be
easily broken.
• Learn about how reaction takes place (i.e., does it
occur in one step or in a series of steps).

3
 Writing Equations for Organic Reactions

• Equations for organic reactions are usually drawn with a single reaction
arrow (→) between the starting material and product.
• The reagent, the chemical substance with which an organic compound
reacts, is sometimes drawn on the left side of the equation with the other
reactants.
• At other times, the reagent is drawn above the arrow.
• Although the solvent is often omitted from the equation, most organic
reactions take place in liquid solvent.

4
 Ways to Write Organic Reactions
Figure 6.1

• The solvent and temperature of the reaction may be

added above or below the arrow.
• The symbols “h” and “” are used for reactions that
require light or heat, respectively.
5
 Writing Equations for Sequential Reactions

• When two sequential reactions are carried out, the steps are
numbered above or below the reaction arrow.
• This convention signifies that the first step occurs before the
second step, and the reagents are added in sequence, not at the
same time.

6
 RECALL: Functional Groups and Electrophiles

• All functional groups contain a heteroatom, a  bond or both.

• These features create electrophilic sites and nucleophilic
sites in a molecule.
• Electron-rich sites (nucleophiles) react with electron poor
sites (electrophiles).
• An electronegative heteroatom like N, O, or X makes a
carbon atom electrophilic as shown below.

7
 Nucleophilic Sites in Molecules
• A lone pair on a heteroatom makes it basic and
nucleophilic.

•  bonds create nucleophilic sites and are more easily

broken than s bonds.

8
 Reaction of  Bonds with Electrophiles

• An electron-rich carbon reacts with an electrophile,

symbolized as E+.

• For example, alkenes contain an electron-rich double

bond, and so they react with electrophiles E+.

9
 Reaction of Nucleophiles with Electrophiles

Alkyl halides possess an electrophilic carbon atom, so they

react with electron-rich nucleophiles.

10
 Substitution Reactions

• Substitution is a reaction in which an atom or a group of

atoms is replaced by another atom or group of atoms.
• In a general substitution, Y replaces Z on a carbon atom.

11
 Substitution Reactions

• Substitution reactions involve s bonds: one s bond breaks and

another forms at the same carbon atom.
• While in some cases Z can be a hydrogen atom, the most
common examples of substitution occur when Z is a heteroatom
that is more electronegative than carbon.

12
 Elimination Reactions

• Elimination is a reaction in which elements of the starting

material are “lost” and a  bond is formed.

13
 Elimination Reactions

• In an elimination reaction, two groups X and Y are removed from a starting

material.
• Two s bonds are broken, and a  bond is formed between adjacent atoms.
• The most common examples of elimination occur when X = H and Y is a
heteroatom more electronegative than carbon.

14
 Addition Reactions

• Addition is a reaction in which elements are added to the

starting material.

15
 Addition Reactions

• In an addition reaction, new groups X and Y are added to the

starting material.
• A  bond is broken and two s bonds are formed.

16
 Relationship of Addition and
Elimination Reactions
• Addition and elimination reactions are exactly opposite.
• A  bond is formed in elimination reactions, whereas a  bond is
broken in addition reactions.
• Often these reactions are reversible.

17
 Sample Problem

Classify each transformation as substitution,

elimination, or addition.
1. 3.

2. 4.
 Sample Problem

Capsaicin is responsible for the

characteristic spicy flavor of
jalapeño and habañero peppers.

What type of organic reaction is this?

 Solution

Capsaicin is responsible for the

characteristic spicy flavor of
jalapeño and habañero peppers.

To determine whether a reaction is a substitution, elimination, or addition with a complex

starting material, concentrate on the functional groups that change. The conversion of
amine X and acid chloride Y to the naturally occurring compound capsaicin is a
substitution reaction, because the N atom of the amine replaces the Cl of the acid
chloride.
 Reaction Mechanisms

• A reaction mechanism is a detailed description of how bonds are

broken and formed as starting material is converted into product.
• A reaction can occur either in one step or a series of steps.

21
 Bond Breaking–Intermediates

• Radicals and carbocations are electrophiles because they contain

an electron-deficient carbon.
• Carbanions are nucleophiles because they contain a carbon with a
lone pair.

22
 Bond Forming

• Bond formation occurs in two different ways.

• Two radicals can each donate one electron to form a two-
electron bond.
• Two ions with unlike charges can come together, with the
negatively charged ion donating both electrons to form the
resulting two-electron bond.
• Bond formation always releases energy.

23
Arrows Used in Organic Reactions

24
 Sample Problem

Use full-headed or half-headed curved arrows to show the movement of

electrons in each equation.

2
 Solution

Use full-headed or half-headed curved arrows to show the movement of

electrons in each equation.

2
 CONCEPT CHECK

Use full-headed or half-headed curved arrows to show the movement of

electrons in each equation.

2
 Oxidation and Reduction Reactions

• Oxidation results in an increase in the number of C-Z bonds.

• Oxidation results in a decrease in the number of C-H bonds.
• Reduction results in a decrease in the number of C-Z bonds.
• Reduction results in an increase in the number of C-H bonds.
Figure 4.18

28
 Sample Problem

Classify each transformation as an oxidation, reduction, or neither.

4
 Hydrolysis

Reaction of an organic chemical with water

to form two or more new substances and
usually means the cleavage of chemical
bonds by the addition of water.

General formula:
AB + H2O → AH + BOH
Hydrolysis
Hydrolysis
 Condensation

Reaction in which two molecules combine to

form a single molecule
A small molecule, often water, is usually
removed during a condensation reaction.
 Condensation

Amino acids are important biological molecules that have an

amine functional group on one end of the molecule and a
carboxylic acid functional group on the other end. When two
amino acids combine in a condensation reaction, a covalent
bond forms between the amine nitrogen of one amino acid and
the carboxyl carbon of the second amino acid.
 Condensation

An esterification is a condensation reaction in which an ester

is formed from an alcohol and a carboxylic acid.