Alkanes of Pharmaceutical Importance – PST05106 Pharmaceutical Organic Chemistry

NTA Level 5 • Semester 1 • PST05106

Alkanes of Pharmaceutical Importance

Pharmaceutical Organic Chemistry • Source Session/Topic 8
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 8: Alkanes of Pharmaceutical Importance.

Total Session Time: 120 minutes

Prerequisites

• None

Learning Tasks

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

• Define alkanes
• List alkanes and their isomers
• Explain nomenclature of alkanes
• Draw chemical structure of alkanes
• List chemical properties of alkanes
• Explain chemical reactions of alkanes

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 |10 minutes |Brainstorming |Definition of Alkanes |

| | |Presentation | |

|3 |15 minutes |Buzzing |Alkanes and their Isomers |

| | |Presentation | |

|4 |15 minutes |Presentation |Nomenclature of Alkanes |

|5 |15 minutes |Presentation |Chemical Structure of Alkanes |

|6 |10 minutes |Brainstorming |Chemical Properties of Alkanes |

| | |Presentation | |

|7 |30 minutes |Group |Chemical Reactions and Uses of |

| | |discussion |Alkanes |

| | |Presentation | |

|8 |10 minutes |Presentation |Key Points |

|9 |10 minutes |Presentation |Evaluation |

SESSION 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 Alkanes (10 minutes).

|Activity: Brainstorming (5 minutes) |

| |

|Ask students to brainstorm on the following question: |

| |

|What is Alkane? |

| |

|ALLOW few students to respond. |

| |

|WRITE their responses on the flip chart/ board. |

| |

|CLARIFY and SUMMARISE by using the content below; |

• Alkane or Paraffin is an acyclic saturated hydrocarbon composed of only

carbons and hydrogen atoms and contain carbon-carbon single bonds.

• Compounds that contain only carbon and hydrogen are called hydrocarbons.

Homologous series (homo is Greek for “the same as”) is a family of

compounds in which each member differs from the next by one methylene

group (CH2).

• The general molecular formula for an alkane is CnH2n+2 where n is an

integer.

• Members (CnH2n+2)

o Methane CH4

o Ethane C2H6

o Propane C3H8

o Butane C4H10

o Pentane C5H12

o Hexane C6H14

o Heptane C7H16

o Octane C8H18

o Nonane C9H20

o Decane C10H22

o Undecane C11H24 etc

• So, if an alkane has one carbon atom, it must have four hydrogen atoms;

if it has two carbon atoms, it must have six hydrogen.

NOTE; Only one possible structure for an alkane with molecular formula CH4

(methane) and molecular formula C2H6 (ethane)

• There are two possible structures for an alkane straight-chain and a

branched structure.

• Both of these structures fulfill the requirement that each carbon forms

four bonds and each hydrogen forms only one bond.

STEP 3: Alkanes and their Isomers (15 minutes).

|Activity: Buzzing (5minutes) |

| |

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

|minutes. |

| |

|What is an isomer? |

|What is isomerism? |

|ALLOW pairs to respond on the question. |

| |

|WRITE their response on the flip chart/board. |

| |

|CLARIFY and SUMMARIZE by using the content below |

• Isomers Refers to different compounds having the same molecular formula

but different structural formula (have different arrangements of atoms in

space).

• In n-alkanes, no carbon is bonded to more than two other carbons, give

rise to a linear chain.

• When carbon is bonded to more than two other carbons, a branched is

formed.

Example.1; C6H14 has 5 isomers as follows:

o Hexane

o 2-Methylpentane

o 3-Methylpentane

o 2,2-Dimethylbutane

o 2,3-Dimethylbutane

Example.2; C7H16 has 9 isomers as follows:

o Heptane

o 2-Methylhexane

o 3-Methylhexane

o 2,2-Dimethylpentane

o 2,3-Dimethylpentane

o 2,4-Dimethylpentane

o 3,3-Dimethylpentane

o 3-Ethylpentane

o 2,2,3-Trimethylbutane

Example 3; C5H12 has 3 isomers which are:

o Pentane

o 2-Methylbutane

o 2,2-Dimethylpropane

Example 4; C4H10 has 2 isomers which are;

o Butane

o 2-Methylpropane

STEP 4: Nomenclature of Alkanes (15 Minutes).

• Rule1. Determine the longest continuous carbon chain.

o This chain is called the parent hydrocarbon.

• Rule 2. In isomeric compounds (II and III), indicate by a number the

Carbon to which the alkyl group is attached.

• Rule 3. In numbering the parent chain, start at whichever end resulting

in the use of the lowest numbers; thus, II is called 2–‐ methylpentane

rather than 4–‐ methylpentane.

• Rule 4. If the same alkyl group occurs more than once as a side chain,

indicate this by the prefix di-, tri-, tetra- etc., to show how many of

these alkyl groups are there and indicate by various numbers the position

of each group, as in 2,2,4‐trimethyl-pentane.

[pic]

• Rule 5 If there are several different alkyl groups attached to the

parent chain, name them in alphabetical order, as in 3,3‐diethyl-5-

isopropyl-4-methyloctane

[pic]

STEP 5: Chemical Structure of Alkanes (15 minutes).

• All acyclic alkanes (unbranded and branched) have the characteristic

molecular formula CnH2n+2, where n is the number of carbon atoms in

the chain.

• Gives the molecular formulas and Lewis structure for the unbranched

and n-alkanes (n stands for normal)

[pic]

STEP 6: Chemical Properties of Alkanes (10 minutes).

|Activity: Brainstorming (5minutes) |

| |

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

|minutes. |

| |

|What are the chemical properties of Alkanes? |

| |

|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 |

• Combustion

o Complete combustion (Under sufficient amount of oxygen (Air)) any

hydrocarbon produces carbon dioxide and water.

o Also, can react with very strong oxidizing agents like Potassium

permanganate, potassium dichromate, Manganese oxide, to produce carbon

dioxide and water.

• Halogenation of alkanes (Substitution of alkanes)

o Halogenation is the replacement of one or more hydrogen atoms in an

organic compound by a halogen (Fluorine, Chlorine Bromine or Iodine).

o Under ultra violet light or temperature that makes up the free radical

chain for halogenation reaction to proceed and that is the first step.

• Cracking

o Cracking is the breakdown of large alkanes under high temperature and

pressure into smaller, more useful alkenes.

o Cracking of alkanes produce a mixture of alkenes and alkanes, cracking

is an example of thermal decomposition reaction.

o Conditions are Temperature of about 500°C and moderately low

pressures.

STEP 7: Chemical Reactions and Uses of Alkanes (30 minutes).

|Activity: Small Group Discussion (15 minutes) |

| |

|DIVIDE students into small groups |

| |

|ASK students to discuss in groups on the following questions |

|What are the reactions involving Alkanes? |

| |

|[pic]REFER Students to Book |

| |

|ALLOW students to discuss for 15 minutes |

| |

|ALLOW each group to present for 5 minutes |

| |

|CLARIFY and SUMMARIZE by using the contents below |

• Combustion

o Complete combustion (Under sufficient amount of oxygen (Air)) any

hydrocarbon produces carbon dioxide and water.

o Example; [pic]

• Halogenation of alkanes (Substitution of alkanes)

o Halogenation is the replacement of one or more hydrogen atoms in an

organic compound by a halogen (Fluorine, Chlorine Bromine or

Iodine).

o Example;

[pic]

• Cracking

o Cracking is the breakdown of a large alkanes under high temperature

and pressure into smaller, more useful alkenes.

o Product of cracking of alkanes are alkenes and alkanes.

o Cracking is an example of thermal decomposition reaction at

temperature of about 500°C and moderately low pressures.

o Example;

[pic]

Uses of alkanes

• The pharmaceutical use of alkane is often used in general anesthesia.

o Alkane is a compound of halothane which is a general anesthetic agent.

• Petroleum and natural gas are largely mixtures of different alkanes.
• On refining, they give liquefied petroleum gas (LPG), gasoline, kerosene,

diesel, furnace oil and wax which are used as fuels.

• Some higher alkanes are used as lubricating oils and as vaseline.
• Alkanes are used as starting materials for the preparation of many other

useful organic compounds.

o For example, methane on chlorinate on gives chloromethane,

dichloromethane, trichloromethane (chloroform) and tetrachloromethane.

STEP 8: Key Points (10 minutes).

• Alkanes or Paraffin is an acyclic saturated hydrocarbon composed of only

carbons and hydrogen atoms and contain carbon-carbon single bonds.

• The alkanes general formula is CnH(2n+2) which is stable for all the
alkanes members, where n= the number of carbon atoms in the molecular

structure.

• The first 3 members of the alkane series, the methane, ethane & propane

have no isomers because there is only one way in arranging the molecule

in 3D structures but the rest of the alkane’s series might have an

isomer, which is called structure isomers.

• There are two basic systems for the naming of alkanes which are common

names also called general or primary names or the un-systematic name and

The IUPAC name, or the systematic name.

• Chemical properties of alkanes involve combustion, halogenation and

cracking.

• Alkanes can be used in preparation of pharmaceuticals such as halothane

which is a general anaesthetic.

STEP 9: Evaluation (10 minutes)

• What are alkanes?
• What are the rules of naming alkanes?
• What are the chemical properties of alkanes?
• What are the uses of alkanes in pharmacy?

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 Rao Nadendla (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.). California, 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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