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Questions and Answers
Penicillin has the capability to treat viral infections.
Penicillin has the capability to treat viral infections.
False
The treatment of disease through surgical methods is typically faster than medical approaches.
The treatment of disease through surgical methods is typically faster than medical approaches.
False
A drug molecule can consist of one or more functional groups arranged in a defined 3D space.
A drug molecule can consist of one or more functional groups arranged in a defined 3D space.
True
Lorazepam at a dosage of 2 mg can cause life-threatening seizures.
Lorazepam at a dosage of 2 mg can cause life-threatening seizures.
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Drug molecules are designed to avoid binding to non-target receptors to reduce toxicity.
Drug molecules are designed to avoid binding to non-target receptors to reduce toxicity.
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Myocardial infarction is treated with a dosage range of 10-12 mg of morphine.
Myocardial infarction is treated with a dosage range of 10-12 mg of morphine.
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Medication aims to provide therapeutic benefits to a limited number of individuals, typically in rich nations.
Medication aims to provide therapeutic benefits to a limited number of individuals, typically in rich nations.
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The impact of therapeutic drugs is considered less significant than public health measures.
The impact of therapeutic drugs is considered less significant than public health measures.
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Phenyl is a molecular fragment that is represented as Ph.
Phenyl is a molecular fragment that is represented as Ph.
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Acetic acid and benzoic acid are both trivial names for the same compound.
Acetic acid and benzoic acid are both trivial names for the same compound.
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The systematic name for the compound known as acetone is propan-2-one.
The systematic name for the compound known as acetone is propan-2-one.
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1,1,1-Trimethyl-3-butene contains four ethyl groups in its structure.
1,1,1-Trimethyl-3-butene contains four ethyl groups in its structure.
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The compound represented as BnBr is benzyl bromide.
The compound represented as BnBr is benzyl bromide.
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Molecules are classified solely based on their physical properties.
Molecules are classified solely based on their physical properties.
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Trans-2-Hexenoic acid has a condensed structural formula of CH3CH2CH2CH=CHCO2H.
Trans-2-Hexenoic acid has a condensed structural formula of CH3CH2CH2CH=CHCO2H.
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In skeletal formulas, the representation of carbon atoms is always required.
In skeletal formulas, the representation of carbon atoms is always required.
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Hydrogens attached to carbon atoms are usually shown in skeletal formulas.
Hydrogens attached to carbon atoms are usually shown in skeletal formulas.
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FGs refer to functional groups in molecular structures.
FGs refer to functional groups in molecular structures.
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The zigzag line is a recommended way to represent chains of atoms in organic molecules.
The zigzag line is a recommended way to represent chains of atoms in organic molecules.
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The IUPAC name of a molecule must always include its molecular formula.
The IUPAC name of a molecule must always include its molecular formula.
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Morphine and alcohol are examples of molecules with no functional groups.
Morphine and alcohol are examples of molecules with no functional groups.
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Drawing molecules can omit individual carbon and hydrogen representations in many cases.
Drawing molecules can omit individual carbon and hydrogen representations in many cases.
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Alkenes are characterized by having only single bonds between carbon atoms.
Alkenes are characterized by having only single bonds between carbon atoms.
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In naming a compound, multiple substituents are indicated by the prefixes di, tri, and tetra.
In naming a compound, multiple substituents are indicated by the prefixes di, tri, and tetra.
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Substituents should be listed in the order of their numerical positions in a compound, ignoring their alphabetical order.
Substituents should be listed in the order of their numerical positions in a compound, ignoring their alphabetical order.
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When numbering the carbon chain, the end that yields the highest numbers for the functional groups should be prioritized.
When numbering the carbon chain, the end that yields the highest numbers for the functional groups should be prioritized.
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All terminal functional groups in organic compounds such as aldehydes and carboxylic acids are assumed to reside on carbon in the chain.
All terminal functional groups in organic compounds such as aldehydes and carboxylic acids are assumed to reside on carbon in the chain.
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The IUPAC name for 2,4-dimethyl-1-pentene would categorize it as a hexane derivative.
The IUPAC name for 2,4-dimethyl-1-pentene would categorize it as a hexane derivative.
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The term 'tert' can be used as a prefix for indicating multiple substituents in nomenclature.
The term 'tert' can be used as a prefix for indicating multiple substituents in nomenclature.
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The numberings of carbon atoms should give the lowest set of numbers for both substituents and functional groups.
The numberings of carbon atoms should give the lowest set of numbers for both substituents and functional groups.
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Cyclohexane can have only a chair shape and not a boat shape.
Cyclohexane can have only a chair shape and not a boat shape.
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The functional group suffix for an alkene is -ene.
The functional group suffix for an alkene is -ene.
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The compound 3-ethyl-4-methylpentane can also be referred to as 4-methyl-3-ethylpentane.
The compound 3-ethyl-4-methylpentane can also be referred to as 4-methyl-3-ethylpentane.
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Ketones contain a carboxyl group and are named with the suffix -oic acid.
Ketones contain a carboxyl group and are named with the suffix -oic acid.
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Ignoring multiplying prefixes is important when determining the alphabetical order of substituents.
Ignoring multiplying prefixes is important when determining the alphabetical order of substituents.
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1,1',2,3,5,6,7,7'-nonamethylheptane is a correctly structured IUPAC name for a hydrocarbon.
1,1',2,3,5,6,7,7'-nonamethylheptane is a correctly structured IUPAC name for a hydrocarbon.
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The systematic naming of branched compounds starts from the end that yields the largest carbon atom number.
The systematic naming of branched compounds starts from the end that yields the largest carbon atom number.
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The suffix -ol is associated with alcohols, indicating the presence of a hydroxyl group.
The suffix -ol is associated with alcohols, indicating the presence of a hydroxyl group.
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Alkyl halides contain carbon atoms bonded to halides and are indicated by the prefix halo- or the suffix -halide.
Alkyl halides contain carbon atoms bonded to halides and are indicated by the prefix halo- or the suffix -halide.
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Ethers contain a nitrogen atom bonded to two carbon chains and are named with the suffix -amine.
Ethers contain a nitrogen atom bonded to two carbon chains and are named with the suffix -amine.
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Nitriles contain a cyano group and are indicated by the prefix cyano- or the suffix -nitrile.
Nitriles contain a cyano group and are indicated by the prefix cyano- or the suffix -nitrile.
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Cyclopropane and cyclopentane both contain a carbon ring structure.
Cyclopropane and cyclopentane both contain a carbon ring structure.
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Alkynes are characterized by the presence of a double bond and are named with the suffix -yne.
Alkynes are characterized by the presence of a double bond and are named with the suffix -yne.
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Study Notes
Introduction to Pharmaceutical Chemistry
- The course is PF1009: Introduction to Pharmaceutical Chemistry
- Lecturer: Dr Tim O’Sullivan
- Email: [email protected]
- Office: 2.05 Cavanagh Building
- P1 Lectures: Wednesdays 3-4pm, LG52
Topics
- Nomenclature
- Carbonyls
- Carboxylic acids
- Esters
- Acid chlorides/anhydrides
- Amides
- Aromatics
- Alkanes
- Alkenes
- Alkynes
- Alkyl halides
- Alcohols
- Epoxides
- Amines
Texts
- Organic Chemistry - J. McMurry
- Beginning Organic Chemistry : Workbook 2 - G.L.Patrick
- (An Introduction to Medicinal Chemistry - G.L.Patrick)
- Partial notes are also available on Canvas
Treatment of Disease
- There are two main approaches to treating disease:
-
Surgical
- Labour intensive
- Time demanding
- Limited number of individuals
- Common in rich nations
-
Medical
- Based on drug molecules
- Large number of people
- Shorter time frame
- Common in developed and developing countries
-
Surgical
Impact of Therapeutic Drugs
- Second only to public health measures in impact on disease
- Examples:
- 100 g of salbutamol sulfate relieves asthma attack
- Intravenous 2 mg of lorazepam stops life-threatening seizures (status epilepticus)
- Myocardial infarction treated with 8-10 mg of morphine.
Drug Molecules
- Contain one or more functional groups
- Arranged in a defined 3D space on a structural framework
- This enables the molecule to bind specifically to a receptor
- Promotes a beneficial biological response
- Prevents binding to untargetted receptors minimizes toxicity.
- Functional groups determine the way a molecule behaves both chemically and biologically.
Drawing Molecules
-
Examples
- H H H O
H C H C C C C C OH H H H H
- H H H O
-
trans-2-Hexenoic acid* (IUPAC name)
-
CH3CH2CH2CH=CHCO2H (Condensed structural formula)
-
(Line-segment formula)
-
Guidelines for Drawing Molecules
- Draw chains as a zigzag line
- Omit hydrogens attached to carbon atoms
- Omit capital Cs representing carbon atoms in skeletal formulas
- May insert Cs and Hs when part of a functional group
Common Functional Groups
Part I
-
Alkanes
- Contain no functional groups
- Suffix: -ane
-
Alkenes
- Contain C=C double bonds
- Also called olefins
- Suffix: -ene
-
Alkynes
- Contain CC triple bonds
- Suffix: -yne
-
Alcohols
- Contain a hydroxyl (OH) group
- Suffix: -ol
-
Ethers
- Contain an alkoxy group (-OR)
- X Y ether
-
Amines
- Contain an amino (NH2) group
- Suffix: -amine or amino-
Part II
-
Alkyl halides
- Contain a halide (-F, -Cl, -Br, -I)
- Halo- or -halide
-
Aldehydes
- Contain a carbonyl group (C=O)
- R-CHO
- Suffix: -al
-
Ketones
- Contain a carbonyl group (C=O)
- R1-CO-R2
- Suffix: -one
-
Carboxylic acids
- Contain a carboxyl (-CO2H) group
- R-CO2H
- Suffix: -oic acid
-
Esters
- Contain a carboxyl group with an extra alkyl (CO2R)
- R1-CO2R2
- Suffix: -ate
-
Nitriles or Cyanides
- Contain a cyano (nitrile) group
- R-CN, -nitrile or cyano-
Systematic Nomenclature
Part I
- IUPAC rules are used for naming
- Suffix indicates functional group
- Prefix indicates number of C atoms
Part II
- Branched compounds named as alkyl derivatives of the longest straight chain
- Length of longest chain provides the parent name
- Straight chain is numbered from the end which produces the smaller numbers for the carbon atoms where the branches occur
- Hyphen must separate numbers from prefixes, numbers, and names
- Numbers can be used for functional groups which are not at a terminal carbon
- i.e. substituents on the chain
Part III (Alkanes)
- Multiple substituents are shown by: di, tri, tetra (not tert!), penta
- Number C-atoms starting from the end of the chain that gives the lowest set of numbers
- If two possible sets are equal, the lowest number is given to the substituent that comes first alphabetically.
- Substituents are listed in alphabetical order
- Ignore multiplying prefixes when alphabetizing
Part IV
- Number chains to give the functional group the lowest number
- Characteristic groups are cited as prefixes in substitutive nomenclature, e.g. halogens
- Terminal functional groups are assumed to be on carbon 1
Nomenclature MCQs
-
Question 1
-
What is the IUPAC name of the compound shown?
-
Answer choices: a. 2,3,4,5,6,7,8-heptamethylnonane b. 1,2,3,4,5-pentamethyl-2,5-isopropylpentane c. 1,1',2,3,5,6,7,7'-nonamethylheptane d.di-(1,2,3-trimethylbutyl)ethane e. None of the above
-
-
Question 2
-
What is the correct IUPAC name for the compound shown?
-
Answer choices: a.Dimethylpentene b. 4,4-Dimethyl-1-pentene c. 2,2-Dimethyl-4-pentene d. 4,4,4-Trimethyl-1-butene e. 1,1,1-Trimethyl-3-butene
-
Trivial Names
- Some compounds are better known by their trivial names
- Examples
- Acetone
- Acetic acid
- Ethanal
- Methanoic acid
- (Ethanoic acid)
- Ethyl ethanoate
- Toluene
- Pyridine
- Benzene
- Phenol
Important Molecular Fragments
- Some molecular fragments have important mechanistic & structural significance
- Examples
- Phenyl (Ph)
- Benzyl (Bn)
- PhOMe
- BnBr
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Description
Test your knowledge on key concepts from the PF1009 course, including nomenclature and functional groups such as carbonyls, carboxylic acids, and amides. This quiz will cover core topics that are crucial for understanding pharmaceutical chemistry and drug treatment approaches.
