MODULE IN BSES 26

ORGANIC CHEMISTRY

Week 17
(January 9 - 13, 2023)

Lomalinda J. Clores

Bachelor of Secondary Education II – Science

 Introduction

This module will acquaint you with the four types of reactions in organic chemistry. Also,
this well help you identify the type of organic reaction based on the given equation. Moreover,
this module will help you understand reaction mechanisms and predict the product.

Intended Learning Outcomes

After successfully completing this module, you should be able to:
1. define organic reactions;
2. describe the different types of organic reactions;
3. identify the type of reactions based on the given equation;
4. explain reaction mechanisms of organic compounds; and
5. predict product of the reaction mechanism.

Pre-test

Directions: There are four general types of organic reactions (addition, elimination,
substitution, or rearrangement). Identify the types of reactions found in the example below.

1) _________________

2) _________________

3) _________________

4) _________________

5) _________________

6) _________________

7) _________________

8) __________________

9) __________________

10) __________________

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 Lesson Discussion

Organic Reactions and Mechanisms

Organic reactions are chemical reactions involving organic compounds. Reaction

mechanism is a complete, step-by-step sequence of how a reaction of organic compounds
takes place. A full mechanism includes details of the order of bond breaking and bond making,

Nucleophile
- a reagent which can donate an electron pair in a reaction
- means nucleus loving and indicates that it attacks regions of low electron density
(positive centers) in the substrate molecule
- is electron rich
- may be negative ions including carbanions or neutral molecules with free
electron pair
- can be represented by a general symbol Nu:--
Examples: Cl-, Br-, I-, CN-, OH-, RCH2-, NH3, RNH2, H2O, ROH

Electrophile
- a reagent which can accept an electron pair in a reaction
- means electron loving and indicates that it attacks regions of high density (negative
centers)
- is electron deficient
- may be positive ions including carbonium ions or neutral molecules with electron
deficient centers
- can be represented by a general symbol E+
Examples: H+, Cl+, I+, Br+, NO2+, R3C+, AlCl3, BF3

Types of Organic Reactions and their Mechanisms

1. Reaction of Alkenes: ADDITION REACTION

The characteristic reaction of alkenes is addition to the double bond according to the
general equation:

Alkenes are commonly described as unsaturated hydrocarbons because they have the
capacity to react with substances which add to them. Alkanes, on the other hand, are said to
be saturated hydrocarbons and are incapable of undergoing addition reactions.

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Here’s the basic pattern: break a C-C multiple bond (also called a π bond) and form two new
single bonds (“σ-bonds” to carbon.

This reaction is called an “addition reaction” and it’s an extremely common type of reaction Note
that the reaction occurs only at the carbons that are a part of a multiple bond – nothing else on
the molecule is affected.

Hydrogenation of alkenes

The relationship between reactants and products in addition reactions can be illustrated
by the hydrogenation of alkenes to yield alkanes. Hydrogenation is the addition of H2 to a
multiple bond. The reaction of hydrogen with ethylene to form ethane is described in the
following:

The bonds in the product are stronger than the bonds in the reactants; two C—H  bonds of
an alkane are formed at the expense of the H—H  bond and the  component of the alkene’s
double bond. The overall reaction is exothermic, and the heat evolved on hydrogenation of
one mole of an alkene is its heat of hydrogenation, H°.

The rate of hydrogenation increases dramatically, however, in the presence of certain finely
divided metal catalysts. Platinum is the hydrogenation catalyst most often used, although
palladium, nickel, and rhodium are also effective.

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 Other examples of hydrogenation are as follows:

Reaction of hydrogen with 2-Methyl-2-butene to form 2-Methyl butane

Reaction of hydrogen with 5,5-Dimethyl(methylene) cyclononane to form 1,1,5-Trimethylcyclononane.

Mechanism

Hydration of alkenes

Many simple alcohols, like ethanol, are usually made by the hydration of alkenes in the
presence of an acid catalyst.
Ethanol is made by the hydration of ethylene in the presence of strong acid such as
sulfuric acid, H2SO4 and phosphoric acid, H3PO4
The equation below represents the hydration reaction.

Ethene Water Ethanol

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Mechanism

Bromination of alkenes (Halogenation)

Ethene Bromine 1,2-Dibromoethane

Ethene reacts with liquid bromine to give 1,2-Dibromoethane. Two bromine atoms are
attached to the two carbon atoms in the ethene molecule.
The bromine atoms break the carbon-to-carbon double bond and from C—Br bonds.
This type of reaction is called addition reaction and the addition of bromine to an alkane is called
bromination.

Mechanism

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Hydrohalogenation of alkene

Ethene Chloroethane
The hydrohalogenation of alkenes involves breaking a carbon to carbon double bond,
followed by the electrophilic addition of a hydrogen atom and halogen. The halide will add to
the more substituted carbon following Markovnikov’s rule. The product is a haloalkane also
called an alkyl halide. (HCl, HBr,or HI are hydrogen halides)

Mechanism

2. ELIMINATION REACTION

Eliminations are the opposite of additions. In an elimination one molecule loses the
elements of another small molecule. Elimination reactions give us a method for preparing
compounds with double and triple bonds.

There is an important an elimination called dehydrohalogenation, a reaction that is used

to prepare alkenes. In dehydrohalogenation, as the word suggests, the elements of a hydrogen
halide are eliminated. An alkyl halide becomes an alkene:

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Mechanism

3. SUBSTITUTION REACTION

Substitutions are the characteristic reactions of saturated compounds such as alkanes

and alkyl halides and of aromatic compounds (even though they are unsaturated). In a
substitution, an atom or group of atoms in a molecule is replaced or substituted by different
atoms or group of atoms.

For example, chloromethane reacts with sodium hydroxide to produce methyl alcohol
and sodium chloride:

In this reaction a hydroxide ion from sodium hydroxide replaces the chlorine of methyl chloride.

Other examples:

(H replaced by Cl)

(I replaced by OH)

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4. REARRANGEMENT

In a rearrangement a molecule undergoes a reorganization of its constituent parts. For

example, heating the following alkene with a strong acid causes the formation of another
isomeric alkene:

In this rearrangement not only have the positions of the double bond and a hydrogen
atom changed, but a methyl group has moved from one carbon to another.

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Rearrangement reactions

1. They can accompany many of the reactions such as substitution, addition, and
elimination reactions.

2. They involve the “movement” of an atom (H in the top two examples, C in the third) from
one carbon to another.

Mechanisms: How Organic Reactions Occur

The particular route an organic takes between reactants and product is called the
reaction mechanism. A full mechanism, includes derails of the order of bond breaking and
bond making, information on intermediates (if any), as well as kinetic and thermodynamic
information.

The most fundamental aspect of mechanism is bond breaking and bond formation.
Bonds can be broken evenly or unevenly – the first type is called homolysis and the second
kind is known as heterolysis.

Homolysis: A----B A + B (radicals)

Electronegativity of A ≈B (A-B is a non-polar bond)
Heterolysis: A----B A+ + :B- (ions)
Electronegativity of A≠B, here B > A (A-B is a polar bond)

Bonds can be made in a similar fashion.

Homogenic bond making: A  + B (radicals) A----B

Heterogenic bond making: A + : B-(ions)
+
A----B

Reactions involving homolysis are called free radical or radical reactions, because of the
odd- electron species (called radicals) that are generated by such a process. Reactions
involving heterolysis are called polar (or ionic) reactions, because of the polarity of the bonds
that are broken in such process. In addition to radical and polar reactions, there is a third, less
common type, known as electrocyclic (or pericyclic) reactions.

Radical Reactions

Although these are less common than polar reactions in organic chemistry, they are
nonetheless important, especially in some biological pathways. Radicals are odd-electron
species and because they are one electron short of a complete outer octet, they tend to be
reactive. They commonly undergo substitution and addition reactions.

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 Worksheet 6. Organic Reactions

1. The following diagram shows the reactants in an addition reaction

a. Draw the structural representation of the final product in this reaction

b. What is the condensed structural representation of the product?

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 References

Brown, W. & Poon, T. (2005). Introduction to Organic Chemistry. 3 rd Edition. John Wiley
& Sons, Inc.
Carey, F. & Atkins, R. (2001). Organic Chemistry. 4nd Edition. McGraw-Hill Companies, NY
Carey, F. & Sundberg, R. (2007). Advanced Organic Chemistry. 5 th Edition. McGraw-Hill
Companies, NY
Daley, R. & Daley, S. (2005). Organic Chemistry: Student's Guide to Success in Organic
Chemistry
Meislech, H. et.al. (1999). Schaums Outline of Theory and Problems of Organic Chemistry. 3 rd
Edition. McGraw-Hill Companies, NY
Moore, J. & Stanitski C. (2015). Chemistry: The Molecular Science. 5 th Edition. Cengage Learning

Prepared by:

LOMALINDA J. CLORES
Course Professor
BSES 26 - Organic Chemistry

Reviewed by:

LEAH C. NAVARRO, EdD

Chairperson, Teacher Education Department

Approved by:

MAT M. NUESTRO
Director, Curriculum and Instruction

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