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Questions and Answers
What is the primary reason functional group chemistry is emphasized for pharmacy students?
What is the primary reason functional group chemistry is emphasized for pharmacy students?
Which term correctly defines a molecule that donates an electron pair to form a bond?
Which term correctly defines a molecule that donates an electron pair to form a bond?
What is NOT a property of drugs that can be deduced from their functional groups?
What is NOT a property of drugs that can be deduced from their functional groups?
Which statement is least accurate regarding the identification of functional groups?
Which statement is least accurate regarding the identification of functional groups?
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What is the significance of hyperconjugation in understanding product distribution patterns?
What is the significance of hyperconjugation in understanding product distribution patterns?
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What is the significance of delocalized electrons in molecules like ozone and aromatic compounds?
What is the significance of delocalized electrons in molecules like ozone and aromatic compounds?
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What is the limitation of using Lewis structures for large organic molecules?
What is the limitation of using Lewis structures for large organic molecules?
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What additional information is needed beyond the molecular formula to understand the structure of a compound like propan-2-ol?
What additional information is needed beyond the molecular formula to understand the structure of a compound like propan-2-ol?
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What does the term 'condensed formula' refer to in the context of drawing organic molecules?
What does the term 'condensed formula' refer to in the context of drawing organic molecules?
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Which element is present in the molecular formula of propan-2-ol?
Which element is present in the molecular formula of propan-2-ol?
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Which statement accurately describes the role of cis-retinal in vision?
Which statement accurately describes the role of cis-retinal in vision?
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What is the primary reason alkenes are more reactive than alkanes?
What is the primary reason alkenes are more reactive than alkanes?
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What process is used to prepare alkenes through the breaking down of hydrocarbons?
What process is used to prepare alkenes through the breaking down of hydrocarbons?
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Which of the following processes is NOT a way to form alkenes?
Which of the following processes is NOT a way to form alkenes?
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What is the effect of visible light on rhodopsin in the context of vision?
What is the effect of visible light on rhodopsin in the context of vision?
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What property of phenols contributes to their increased acidity compared to aliphatic alcohols?
What property of phenols contributes to their increased acidity compared to aliphatic alcohols?
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Which factor affects the boiling point of phenols significantly?
Which factor affects the boiling point of phenols significantly?
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What is the correct bond length of the C-O bond in phenols?
What is the correct bond length of the C-O bond in phenols?
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How does the hydroxyl group in phenol influence its solubility in water?
How does the hydroxyl group in phenol influence its solubility in water?
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What term best describes the overall structure of phenols?
What term best describes the overall structure of phenols?
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Which hormone, related to phenols, is primarily involved in the 'fight or flight' response?
Which hormone, related to phenols, is primarily involved in the 'fight or flight' response?
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What is the typical pKa value of phenols, indicating their acidity level?
What is the typical pKa value of phenols, indicating their acidity level?
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Which aspect does not contribute to the unique properties of phenols compared to aliphatic alcohols?
Which aspect does not contribute to the unique properties of phenols compared to aliphatic alcohols?
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What determines the product formed during the addition of bromine to an alkene?
What determines the product formed during the addition of bromine to an alkene?
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What intermediate is formed during the addition of bromine to an alkene?
What intermediate is formed during the addition of bromine to an alkene?
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Which of the following statements is true about the hydrogenation of alkenes?
Which of the following statements is true about the hydrogenation of alkenes?
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During the addition of halogens to an alkene, what is the nature of the reaction?
During the addition of halogens to an alkene, what is the nature of the reaction?
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Which catalyst is commonly used for the hydrogenation of alkenes?
Which catalyst is commonly used for the hydrogenation of alkenes?
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In the context of halogen addition to alkenes, what does the term 'vicinal dihalide' refer to?
In the context of halogen addition to alkenes, what does the term 'vicinal dihalide' refer to?
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What is the main factor influencing the regioselectivity of the addition reactions of alkenes?
What is the main factor influencing the regioselectivity of the addition reactions of alkenes?
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Which of the following reagents would typically be used for the oxidation of alkenes?
Which of the following reagents would typically be used for the oxidation of alkenes?
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During the addition of halogens, what happens to the bromide ion?
During the addition of halogens, what happens to the bromide ion?
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What characterizes an SN1 reaction mechanism?
What characterizes an SN1 reaction mechanism?
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In nucleophilic substitution reactions, which statement is true regarding the role of nucleophiles?
In nucleophilic substitution reactions, which statement is true regarding the role of nucleophiles?
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Which order of reaction kinetics can SN2 reactions follow?
Which order of reaction kinetics can SN2 reactions follow?
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Which of the following best describes the nomenclature used for nucleophilic substitution mechanisms?
Which of the following best describes the nomenclature used for nucleophilic substitution mechanisms?
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What distinguishes a bimolecular reaction mechanism in the context of nucleophilic substitution?
What distinguishes a bimolecular reaction mechanism in the context of nucleophilic substitution?
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Which statement about haloalkanes is correct?
Which statement about haloalkanes is correct?
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What is an essential feature in determining whether a reaction proceeds via SN1 or SN2 mechanisms?
What is an essential feature in determining whether a reaction proceeds via SN1 or SN2 mechanisms?
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Which of the following correctly identifies the steps in an SN1 reaction mechanism?
Which of the following correctly identifies the steps in an SN1 reaction mechanism?
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Heterolysis involves bond cleavage where both electrons stay with one atom.
Heterolysis involves bond cleavage where both electrons stay with one atom.
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Homolysis is characterized by the movement of two electrons to one of the bonding atoms.
Homolysis is characterized by the movement of two electrons to one of the bonding atoms.
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Double-headed curly arrows are used to indicate the movement of a single electron in polar mechanisms.
Double-headed curly arrows are used to indicate the movement of a single electron in polar mechanisms.
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The use of curly arrows is irrelevant to the understanding of reaction mechanisms.
The use of curly arrows is irrelevant to the understanding of reaction mechanisms.
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Curly arrows can show the movement of electrons in both homolysis and heterolysis reactions.
Curly arrows can show the movement of electrons in both homolysis and heterolysis reactions.
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The two oxygen atoms in nitromethane are different from each other.
The two oxygen atoms in nitromethane are different from each other.
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Resonance forms of a molecule represent a single, unchanging structure.
Resonance forms of a molecule represent a single, unchanging structure.
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The resonance contributors of nitromethane are typically depicted with a double-headed arrow.
The resonance contributors of nitromethane are typically depicted with a double-headed arrow.
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Neither of the Lewis structures for nitromethane is a correct representation of its true structure.
Neither of the Lewis structures for nitromethane is a correct representation of its true structure.
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In nitromethane, the structure oscillates between its resonance forms.
In nitromethane, the structure oscillates between its resonance forms.
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The N-O bonds in nitromethane are of unequal lengths and strengths.
The N-O bonds in nitromethane are of unequal lengths and strengths.
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Resonance structures can be accurately drawn using basic Lewis structure conventions.
Resonance structures can be accurately drawn using basic Lewis structure conventions.
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Resonance forms can help chemists predict the actual behavior of molecules.
Resonance forms can help chemists predict the actual behavior of molecules.
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Delocalized electrons contribute to the overall stability of a molecule.
Delocalized electrons contribute to the overall stability of a molecule.
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Oxidation in drug molecules is characterized by a decrease in the number of bonds to oxygen.
Oxidation in drug molecules is characterized by a decrease in the number of bonds to oxygen.
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The most stable resonance form contributes less to the overall structure compared to less stable forms.
The most stable resonance form contributes less to the overall structure compared to less stable forms.
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Auto-oxidation of drugs can lead to degradation under conditions such as light and heat.
Auto-oxidation of drugs can lead to degradation under conditions such as light and heat.
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Increased covalent bonds between atoms in a resonance form decreases its stability.
Increased covalent bonds between atoms in a resonance form decreases its stability.
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Charge separation in a molecule enhances its stability.
Charge separation in a molecule enhances its stability.
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Auto-oxidation involves the gain of electrons in drug molecules.
Auto-oxidation involves the gain of electrons in drug molecules.
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Tertiary radicals are the least stable due to having the least amount of carbon atoms bonded to them.
Tertiary radicals are the least stable due to having the least amount of carbon atoms bonded to them.
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The presence of radical processes during oxidation implies an increase in the number of bonds to hydrogen.
The presence of radical processes during oxidation implies an increase in the number of bonds to hydrogen.
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Hyperconjugation involves the interaction of electrons in a $ ext{π}$-bond with an adjacent filled p orbital.
Hyperconjugation involves the interaction of electrons in a $ ext{π}$-bond with an adjacent filled p orbital.
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The benzyl radical and the allyl radical are examples of radicals that exhibit unusual stability due to resonance.
The benzyl radical and the allyl radical are examples of radicals that exhibit unusual stability due to resonance.
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A primary radical is more stable than a secondary radical because it has more carbon atoms bonded.
A primary radical is more stable than a secondary radical because it has more carbon atoms bonded.
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Alkyl groups stabilize radicals primarily through inductive effects.
Alkyl groups stabilize radicals primarily through inductive effects.
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The distribution of substituted products in reactions is solely determined by temperature.
The distribution of substituted products in reactions is solely determined by temperature.
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The stability of a radical increases with the number of neighboring carbon atoms due to hyperconjugation.
The stability of a radical increases with the number of neighboring carbon atoms due to hyperconjugation.
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Resonance stabilizes carbocations in a manner similar to radicals.
Resonance stabilizes carbocations in a manner similar to radicals.
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The stability order of radicals is tertiary > secondary > primary > methyl.
The stability order of radicals is tertiary > secondary > primary > methyl.
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Radical stability does not influence the product distribution in free-radical substitution reactions.
Radical stability does not influence the product distribution in free-radical substitution reactions.
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Aldehydes can be reduced to primary alcohols using lithium aluminium hydride.
Aldehydes can be reduced to primary alcohols using lithium aluminium hydride.
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Esters can be reduced using sodium borohydride.
Esters can be reduced using sodium borohydride.
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Ketones can yield secondary alcohols upon reduction.
Ketones can yield secondary alcohols upon reduction.
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Sodium borohydride is a source of hydride ions during the reduction of ketones and aldehydes.
Sodium borohydride is a source of hydride ions during the reduction of ketones and aldehydes.
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Carboxylic acids cannot be reduced to alcohols.
Carboxylic acids cannot be reduced to alcohols.
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The hydride addition to the carbonyl group occurs irrespective of the type of carbonyl compound.
The hydride addition to the carbonyl group occurs irrespective of the type of carbonyl compound.
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Aldehydes and ketones can both be reduced to alcohols using LiAlH4.
Aldehydes and ketones can both be reduced to alcohols using LiAlH4.
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Primary alcohols can be oxidized back to carboxylic acids.
Primary alcohols can be oxidized back to carboxylic acids.
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All carbonyl compounds respond the same way to reducing agents.
All carbonyl compounds respond the same way to reducing agents.
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Lithium aluminium hydride can reduce both aldehydes and esters to alcohols.
Lithium aluminium hydride can reduce both aldehydes and esters to alcohols.
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Vinylic carbocations are primarily formed during the addition reactions of alkynes when following Markovnikov's Rule.
Vinylic carbocations are primarily formed during the addition reactions of alkynes when following Markovnikov's Rule.
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Anti-Markovnikov addition of H-Br occurs without the presence of a radical initiator.
Anti-Markovnikov addition of H-Br occurs without the presence of a radical initiator.
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Tautomerization is the process that converts enols into more stable ketones in hydration reactions of alkynes.
Tautomerization is the process that converts enols into more stable ketones in hydration reactions of alkynes.
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The addition of H2O to alkynes results in the formation of aldehydes instead of ketones.
The addition of H2O to alkynes results in the formation of aldehydes instead of ketones.
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A Lindlar catalyst can be used to stop the hydrogenation of alkynes at the alkene stage.
A Lindlar catalyst can be used to stop the hydrogenation of alkynes at the alkene stage.
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Trans (anti) addition of hydrogen during hydrogenation is not possible in alkynes.
Trans (anti) addition of hydrogen during hydrogenation is not possible in alkynes.
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Hydration of alkynes proceeds through a mechanism similar to that used for alkenes.
Hydration of alkynes proceeds through a mechanism similar to that used for alkenes.
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Geminal dihaloalkanes are compounds characterized by two halogen atoms attached to the same carbon atom.
Geminal dihaloalkanes are compounds characterized by two halogen atoms attached to the same carbon atom.
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Radical initiators, such as H2O2, are necessary for the addition of halogens to alkynes.
Radical initiators, such as H2O2, are necessary for the addition of halogens to alkynes.
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More complex alkynes yield several ketone products due to multiple equally stable intermediates formed during reactions.
More complex alkynes yield several ketone products due to multiple equally stable intermediates formed during reactions.
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The term 'tautomerization' refers specifically to the conversion of ketones to enols.
The term 'tautomerization' refers specifically to the conversion of ketones to enols.
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The hydrogenation of alkynes results in a single final product regardless of the catalyst used.
The hydrogenation of alkynes results in a single final product regardless of the catalyst used.
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Tetrahaloalkanes can be produced from alkynes through the addition of halogens twice.
Tetrahaloalkanes can be produced from alkynes through the addition of halogens twice.
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Study Notes
MPharm Programme PHA111 Functional Group Chemistry
- The week 10 and week 11 lectures cover functional group chemistry, focusing on alkanes, alkenes, alkynes, alcohols, phenols, amines, haloalkanes, and relevant reactions.
- The course aims to explain how functional groups influence the properties and reactivity of organic molecules, including drugs.
- Learning Objectives for week 10: Appreciate the importance of functional groups in pharmacy; Define reaction mechanisms; Identify nucleophiles/electrophiles etc.; and learn how to identify functional groups in drug molecules.
- Learning Objectives for week 11: Identify and understand differences in physical properties of alcohols/haloalkanes/phenols; List reactions used to prepare alcohols; and understand nucleophilic substitution reactions of alcohols and haloalkanes.
- Learning Objectives for week 11 (additional): Identify and understand differences in physical properties of amines; describe the synthesis of amines; understand nucleophilic substitutions of amines; recognise the different types of secondary and tertiary amines; and classify amines.
Functional Groups
- Functional group chemistry is a critical aspect of understanding drug molecules and their properties.
- Understanding the chemistry of functional groups enables the determination of drug properties.
- Key properties include ionization, solubility (lipid vs. aqueous), absorption, distribution, metabolism, and excretion (ADME).
What is a Functional Group?
- Most drugs are composed of two parts: a hydrocarbon part and a functional group (FG).
- The hydrocarbon part is usually unreactive.
- The functional group is where most reactions/interactions occur.
- Molecules having the same functional group generally have similar properties and characteristic reactivities.
- Examples of functional groups are given in the lecture materials.
Chemical Similarity
- The lecture uses an example of extreme bronchospasm to illustrate the concept of chemical similarity in drug molecules.
- Different structures showing the same functional group are examples
What is a Functional Group (continued)
- The different types of hydrocarbons including alkanes, alkenes, alkynes, alcohols, and phenols are covered.
- The specific groups of each hydrocarbon are further explained.
- Examples and diagrams demonstrate different structures for each group.
3D Representations
- sp³ hybridized carbon atoms have a tetrahedral shape.
- 3D structures are represented using wedged and hashed bonds.
- Chiral centers (carbon atoms with four different groups attached) are crucial for understanding chiral molecules.
Reactivity and Reaction Mechanisms
- A chemical mechanism is a detailed step-by-step description of a chemical process.
- Chemical reactions involve the movement of electrons.
- Reactivity can be classified as ionic/polar or radical, depending on the movement of electrons.
Nucleophile
- A nucleophile is electron-rich, drawn with a curly arrow starting at the electron rich center.
- Charged and uncharged nucleophiles are both discussed and exemplified.
Electrophile
- An electrophile is electron-poor, drawn with a curly arrow ending at the electron poor center.
- Charged and uncharged electrophiles are covered.
Leaving Groups
- Leaving groups are ions or neutral molecules displaced from a reactant in a mechanistic sequence.
- Good leaving groups form stable ions or neutral molecules after leaving the substrate.
- Standard abbreviations are provided.
Bond Cleavage
- Heterolytic cleavage involves both electrons moving to one atom.
- Homolytic cleavage involves each atom retaining one electron.
Curly Arrows - Polar Mechanisms
- A double-headed curly arrow denotes the movement of two electrons.
- The lecture notes emphasize precise arrow placement for clarity.
- The various components (electron rich centers, negative charge, lone pairs, and electron-rich bonds) and their relative positions in a molecule are explained.
Curly Arrows - Radical Mechanisms
- The movement of a single electron is indicated by a single-headed curly arrow.
- Radicals must donate/accept one electron to form/break a bond.
Transition States and Intermediates
- Reaction mechanisms can involve transition states and/or intermediates.
- Graphical diagrams are provided depicting the energy change over time involved in reactions.
- The concept of activation energy is explained visually.
- The distinction between transition states and intermediates is explained.
Why Study Mechanisms?
- The need for a thorough understanding of drug formation, drug-target interactions, and reaction mechanisms for predicting metabolic drug stability is emphasized.
Penicillins MOA
- A detailed example of covalent inhibition.
- Explains how the reaction proceeds from an ester to an amide.
Hydrocarbon Compounds
- The three main types are aliphatic, aromatic, and saturated.
- Each of these are further broken down into smaller categories.
- The sub-types are explained through examples and diagrams.
Alkane
- Saturated compounds containing only C-C and C-H bonds with no double or triple bonds.
- These are usually unreactive.
Alkanes: Physical Properties
- Melting/boiling points increase with molecular weight and chain length.
- Weak London dispersion forces are the only intermolecular forces.
Alkanes: Reactivity
- Reactions include combustion, halogenation.
- Halogenation requires high temperatures or light.
- Radical halogenation is a multi-step process.
Alkanes: Halogenation
- Halogenation of alkanes follows a radical mechanism.
- Three main steps of the radical mechanism are highlighted (initiation, propagation, termination) and visual representations.
Radical Stability
- Factors affecting radical stability, such as the number of carbon atoms bonded to the radical center, are outlined.
- Hyperconjugation and/or resonance stabilization affect the stability of radicals.
- Examples are shown of radicals being generated from butane.
Hyperconjugation
- Hyperconjugation is a stabilizing interaction between σ electrons and an unfilled p orbital or a π orbital.
- This phenomenon extends the molecular orbital, increasing the stability of the system and described via suitable examples.
Radical Stability (continued)
- The stability of different radicals (methyl, primary, secondary, tertiary, benzyl, allyl) is compared.
- Resonance delocalization of electrons in radicals increases their stability, specifically in benzyl and allyl radicals.
Resonance Contributors and Hybrids
- Resonance structures (often visualized as molecules fluctuating between drawings) show different arrangements of electrons in a molecule—the actual molecule is a hybrid of all possible resonance forms.
- The concept of resonance contributors and resonance hybrids is illustrated visually with various examples.
Resonance Structures
- Resonance structures, not isomers, are alternative representations of the same molecule.
- They are connected by using double-headed arrows.
Resonance
- Resonance shows delocalization of electron/charge through resonance structures.
Resonance Structures (continued)
- The stability of resonance structures relates to the number of covalent bonds.
- The most stable resonance structure makes the greatest contribution to the molecule.
Oxidation – Radical Process
- Autoxidation, a radical process, is a significant cause of drug degradation.
- Autoxidation leads to a loss of electrons and increases in bonds to oxygen.
Functional Group Chemistry 2
- The week 11 lectures cover the reactivity of alkenes and alkynes, including electrophilic addition (Markovnikov's rule) and discuss the role and importance of chiral molecules.
Alkenes - Summary
- Contains double bonds - are more reactive than alkanes.
- The different types of isomers, such as cis and trans isomers, are described due to restricted rotation around the double bond
- Reactivity of alkenes is discussed.
Alkenes: Isomers and Vision
- Cis-retinal isomerization is central to vision.
- Light absorption triggers isomerization. Alkenes are key in this process.
Alkenes: Reactivity
- Alkene reactions discussed in the lecture include various reactions such as cracking, elimination (dehydrohalogenation and dehydration), addition reactions (electrophilic and homolytic), hydrogenation, and halogenation where different mechanisms are examined.
Alkenes: Addition Reactions
- Different types of addition reactions are included: electrophilic (with a positive charge seeking electrons) and homolytic.
Alkenes: Reactivity (Summary)
- Markovnikov/Anti-Markovnikov additions, including the principles behind these reactions.
Alkenes: Hydration
- Markovnikov addition of water to alkenes.
- Le Chatelier's principle is used to promote the addition reaction.
Alkenes: Anti-Markovnikov Addition
- Anti-Markovnikov addition requires peroxide as a radical initiator.
Alkenes: Addition of Halogens
- Additions of halogens to alkenes, especially Br2 and Cl2, are explained in detail.
Alkenes: Hydrogenation
- Hydrogenation (addition of hydrogen across a double bond) is a reaction that is stereospecific and requires a catalyst.
- The reaction can be stopped at the alkene stage.
Alkynes: Structure
- Contains triple bonds.
- Internal/terminal triple bonds exist, with reactivity being controlled by electron-rich C-C triple bonds.
Alkynes: Physical Properties
- Data on the boiling points of different terminal and internal alkynes.
- Internal alkynes have a higher boiling point than terminal alkynes.
Alkynes: Relative Acidity
- The relative electronegativities of carbon atoms are compared.
Alkynes: Reactivity
- Alkynes are more reactive than alkenes.
- Similar reactions to alkenes like addition reactions with H-X, X-X, H-H, and H-OH are described.
- Examples of alkylation of terminal alkynes are shown using a strong base.
Alkynes: Addition of HX
- Sequential addition of HX.
- Markovnikov's Rule and vinylic carbocation intermediates are involved.
Alkynes: Addition Reactions
- Anti-Markovnikov addition (with a radical initiator present).
- Halogenation reactions proceed similarly to alkenes.
Alkynes: Hydration
- Hydration of alkynes and the formation of ketones
Alkynes: Hydrogenation
- Hydrogenation reaction.
- Use of Lindlar's catalyst.
Alkynes: Versatile Reagents
- Summary of the reactions/types of molecules (alkynes) involved.
- Overview of useful reagents used.
Functional Group Chemistry 3 - Learning Objectives
- Describing and explaining differences in physical properties of alcohols (aliphatic, phenols, haloalkanes).
- Listing the reactions that alcohols undergo.
- Reactivity of alcohols and alkyl halides with regards to nucleophilic substitution reactions.
Alcohols - General Properties
- Alcohols and their classifications.
- Sub-classification into their types (primary, secondary, and tertiary).
- How alcohols act as nucleophiles
- Sub-classification into different types of alcohols
Alcohols: pKa
- Factors influencing alcohol acidity.
- Alkyl groups positively affecting acidity
- Halogens negatively affecting acidity
- Resonance structure to stabilise phenoxide ion
Alcohols: Physical Properties
- Solubility of alcohols with water.
- Like dissolves like.
- Boiling points increase compared to the analogous alkane.
Alcohols: Preparation
- Methods for preparing various types of alcohols.
- Reactions such as hydration of alkenes, alkyl halide hydrolysis reactions, and reduction of carbonyl compounds are covered.
Reduction of Carbonyl Compounds
- Methods of reduction, such as using sodium borohydride and lithium aluminum hydride to reduce aldehydes and ketones (via hydrogen transfer).
Alcohols: Useful Reagents
- Key reagents/reactions.
Alcohols: Reactivity
- Complete combustion; alkoxide formation; ester formation; oxidation reactions; reactions with HX; conversion to haloalkanes
Ester Formation
- Fischer esterification is the classical method for forming esters.
Oxidation
- Oxidation reactions using high oxidation state metal salts and/or other reagents.
- Biological oxidation is a two-step procedure.
Haloalkanes: General
- Structure of haloalkanes.
- Reactivity as electrophiles and how they are affected by the nature of the halogen and alkyl groups.
Haloalkanes: Anaesthetics
- Uses of haloalkanes in anesthetic procedures.
- Factors relating to the choice and use of particular haloalkanes.
Haloalkanes: Physical Properties
- Boiling points.
- Density.
- Solubility.
Haloalkanes: Reactivity
- Free radical substitution of alkanes; electrophilic addition; halogenation of alkenes/alkynes; halogenation of alcohols.
- Nucleophilic substitution reactions.
SN1 and SN2 Reactions
- Mechanisms and characteristics of SN1 and SN2 reactions
- Explains the differences regarding rates of reaction with different types and sizes of alkyl substituents.
Nature of the Nucleophile
- Nucleophilicity of the group attacking the substrate.
Nature of the Nucleophile (continued)
- Basicity and its relationship to nucleophilicity.
Solvent Effects
- How solvents affect S$_\text{N}2$ reactions.
- Polar aprotic solvents.
Nature of the Leaving Group
- Properties of good leaving groups, including stability as an anion.
SN1 Reaction Mechanism
- The rate-determining step (RDS) is the loss of the leaving group which forms a carbocation intermediate.
Nature of the Alkyl Substituent
- The stability of carbocations and its relationship to the stability of the alkyl group substituent.
Racemisation of Stereocentres
- The SN1 reaction of a chiral alkyl halide produces a racemic mixture.
Characteristics of the SN1 Reaction
- Tertiary alkyl halides are more reactive.
- Stability of carbocation intermediates.
- Allylic and benzylic halides are more reactive to SN2 mechanism
A Note: Vinyl and Aryl Halides
- Vinyl and aryl halides do not react via S$\text{N}1$ or S$\text{N}2$.
Nucleophilic Substitution Examples in Biology/Pharmacy
- Examples of nucleophilic substitutions used in biological systems and drug synthesis, specifically, methylation.
SN1 vs SN2 Summary
- Summarizes reaction mechanisms, reaction types, and relative reactivity.
Amines: Occurrence
- Examples of amines in biological molecules.
Synthesis of Amines
- Different methods for synthesizing amines (reduction of nitriles and amides, reduction of imines) and the considerations for monoalkylation.
Reactions with Carboxylic Acid Derivatives
- Reactions in which primary/secondary amines can react with acid chlorides, amides, and sulfonyl chlorides.
Properties of Amines
- Structure and bonding characteristics, including hybridization and presence of lone pairs in amines.
- Lone pairs make amines basic and nucleophiles.
Amines - Classification
- Sub-classification of amines into primary, secondary, tertiary and quaternary ammonium salts.
Amines - Hydrogen Bonding
- Hydrogen bonding features of amines.
- Explains the difference in H-bonding ability between amines and alcohols.
Amine Salts
- Properties of amine salts.
- Includes properties such as water solubility, and the role of these properties in formulations of amine drugs.
Acid/Base Properties of Amino Acids
- Explains how amino acids behave like acids and bases in solution.
- Details of the Zwitterion as the dipolar ion that amino acids can exist as.
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Description
Test your knowledge on functional group chemistry relevant to pharmacy students. This quiz covers essential concepts such as electron pair donation, drug properties determination, and the limitations of Lewis structures. Assess your understanding of significant molecular characteristics and their implications in drug design and action.
