Chemical Reaction in Organic Compounds – PST05106 Pharmaceutical Organic Chemistry

NTA Level 5 • Semester 1 • PST05106

Chemical Reaction in Organic Compounds

Pharmaceutical Organic Chemistry • Source Session/Topic 6
Full source-text version: all educational wording from the extracted learning source is retained; only presenter/tutor metadata and web-layout noise are removed, while formatting is improved for readability.

Session 6: Chemical Reaction in Organic Compounds.

Total Session Time: 60 minutes

Prerequisites

• None

Students Learning Tasks

By the end of this session students are expected to be able to:

• Define term chemical reaction
• List types of chemical reactions in organic compounds
• Explain chemical reactions in organic compounds

Resources Needed:

• Flip charts, marker pens, and masking tape.
• Black/white board and chalk/whiteboard markers.

SESSION OVERVIEW

|Step |Time |Activity/ |Content |

| | |Method | |

|1 |05 minutes |Presentation |Introduction, Learning Tasks |

|2 |15 minutes |Presentation |Definition of the term chemical |

| | |Buzzing |reaction |

|3 | |Group |Types of chemical reactions |

| |30 minutes |discussion |involving organic compounds |

| | |Presentation | |

|4 |05 minutes |Presentation |Key Points |

|5 | | Presentation |Evaluation |

| |05 minutes | | |

CONTENTS

STEP 1: Presentation of Session Title and Learning Tasks (5 minutes)

READ or ASK students to read the learning tasks and clarify.

ASK students if they have any questions before continuing.

STEP 2: Definition of Chemical Reaction (15 minutes)

|Activity: Buzzing (10minutes) |

| |

|ASK students to pair up and buzz on the following question for 5 |

|minutes |

| |

|What is chemical reaction? |

| |

|ALLOW pairs to respond on the question |

| |

|WRITE their response on the flip chart/board |

| |

|CLARIFY and SUMMARIZE by using the content in the table 1 below |

Definition

• A chemical reaction is process in which a substance is transformed into a

new substance through chemical change, OR

• Chemical reactions, a process in which one or more substances, the

reactants, are converted to one or more different substances, the

products, substances are either chemical elements or compounds.

• A chemical reaction rearranges the constituent atoms of the reactants to

create different substances as products.

STEP 3: Types of Chemical Reactions Involving Organic Compounds (30

minutes).

|Activity: Small Group Discussion (20 minutes) |

| |

|DIVIDE students into small manageable groups. |

|ASK students to discuss on the following question. |

| |

|What are the types of chemical reactions involving organic compounds? |

| |

|ALLOW students to discuss for 15 minutes |

|ALLOW few groups to present for 5 minutes and the rest to add points |

|not mentioned. |

| |

|CLARIFY and SUMMARIZE by using the contents below |

There are five main types of organic reactions that can take place. They

are as follows:

• Substitution reactions
• Elimination reactions
• Addition reactions
• Radical reactions
• Oxidation-Reduction Reactions

Let us study each of these reactions in detail, to understand more about

them.

[pic]

• Substitution Reactions

o In a substitution reaction, one atom or a group of atoms take place of

another atom or a group of atoms which leads to the formation of an

altogether new substance.

o We can take an example of C – Cl bond, in which the carbon atom

usually has a partial positive charge due to the presence of highly

electronegative chlorine atoms.

o In a nucleophilic substitution reaction, it is important that the

nucleophile must have a pair of electrons and it also should have a

high affinity for the electropositive species in comparison to the

substituent which was originally present in the element.

o In order for the substitution reaction to occur, there are certain

conditions that have to be present such as maintaining low

temperatures same as room temperature.

• Elimination Reactions

o These are reactions which involve the elimination and removal of the

adjacent atoms.

o After these multiple bonds are simultaneously formed and there is a

release of small molecules as product.

o One of the examples of a typical elimination reaction is the

conversion of ethyl chloride to ethylene.

o CH3CH2Cl → CH2= CH2 + HCl

o In the above reaction, the eliminated molecule is HCl, which can form

out of the combination of H+ from the carbon atom which is on the left

side and Cl– from the carbon atom which is on the right side.

• Addition Reactions

o An addition reaction is simply just the opposite of an elimination

reaction.

o In an addition reaction, the components or molecules of A and B are

added to the carbon-carbon multiple bonds and this is called an

addition reaction.

o In the reaction given below when HCl is added to ethylene, it will

give us ethylene chloride.

HCl + CH2 = CH2 → CH3CH2Cl
• Radical Reactions

o Most of the organic reactions involve radicals and their movement.

o Addition of a halogen to a typically saturated hydrocarbon involves

free radical mechanism.

o There are usually three stages involved in a radical reaction which

are;

▪ initiation
▪ propagation
▪ termination

o Initially when the weak bond is broken initiation of the reaction

takes place with the formation of free radicals.

o After that when the halogen is added to the hydrocarbon a radical is

produced and finally, it gives alkyl halide.

• Oxidation Reduction reactions (REDOX)

o Electrons in an organic redox reaction often are transferred in the

form of a hydride ion – a proton and two electrons.

o Because they occur in conjunction with the transfer of a proton, these

are commonly referred to

as hydrogenation and dehydrogenation reactions: a hydride plus a

proton adds up to a hydrogen (H2) molecule.

o When a carbon atom in an organic compound loses a bond to hydrogen and

gains a new bond to a heteroatom (or to another carbon), this means

the compound has been dehydrogenated, or oxidized.

o A very common biochemical example is the oxidation of an alcohol to a

ketone or aldehyde:

[pic]

o Conversely, when a carbon atom in an organic compound gains a bond to

hydrogen and loses a bond to a heteroatom (or to another carbon atom),

it means the compound has been hydrogenated, or reduced.

o The hydrogenation of a ketone to an alcohol, for example, is overall

the reverse of the alcohol dehydrogenation shown above.

o Illustrated below is another common possibility, the hydrogenation

(reduction) of an alkene to an alkane

[pic]

STEP 4: Key Points (5 minutes)

• Chemical reactions is a process in which one or more substances, the

reactants, are converted to one or more different substances, the

products, substances are either chemical elements or compounds.

• Types of organic reactions include substitution reactions, elimination

reactions, addition reactions, radical reactions and Oxidation-Reduction

Reactions.

STEP 5: Evaluation (10 minutes).

• What is a chemical reaction?
• What is a substitution reaction?
• What is an addition reaction?
• What is a REDOX reaction?

References

Ternay, A.L (1976). Contemporary Organic Chemistry. Philadelphia, United

States: W.B. Saunders Co.

Morrison R.T and Boyd R N (1997). Organic Chemistry (6th Ed.). New Delhi,

India: Prentice Hall of India

Graham Solomon et al (2014). Organic Chemistry (11th Ed.). New Jeysey,

United States: John Willey and Sons.

Rama R. N. (2005). Principles of Pharmaceutical Organic Chemistry. New

Delhi, India: MacMillan Publishers

Bruice Y (2013). Organic Chemistry (7th ed.). New York, United States:

Prentice Hall Pearson.

Delgado J. N. Et al (1998). Wilson and Gisvold's Textbook of Organic

Medicinal and Pharmaceutical Chemistry (10th Ed.). Calfornia, United

States: Lippincott Williams

Bhassin S.K, Gupta R.(2013). Pharmaceutical organic chemistry (E-book

Kindle edition). New Delhi, India: Elsevier Publishing Services

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