Functional group 1

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Questions and Answers

What part of a drug molecule typically remains unreactive?

  • Analytical choice
  • Functional group
  • Therapeutic effect
  • Hydrocarbon part (correct)

Which of the following statements best describes functional groups?

  • They cause diverse properties among similar organic molecules.
  • They solely determine the hydrocarbon part of a molecule.
  • They are reactive parts of molecules that contribute to similar properties. (correct)
  • They have no impact on the reactivity of organic compounds.

Why is understanding physiochemical properties important in medicinal chemistry?

  • They dictate the syntactic structure of organic molecules.
  • They solely determine the metabolism efficiency of a drug.
  • They help distinguish between functional and non-functional groups.
  • They influence receptor binding and the therapeutic effect of drugs. (correct)

What typically influences the choice of analytical methods in pharmacology?

<p>The physiochemical properties of the substances being analyzed. (B)</p> Signup and view all the answers

What is a likely outcome when molecules have the same functional group?

<p>They share similar chemical reactivities and properties. (A)</p> Signup and view all the answers

What shape do sp3 hybridized carbon atoms adopt?

<p>Tetrahedral (B)</p> Signup and view all the answers

In a 3D representation of molecules, which bond indicates that it is pointing towards the viewer?

<p>Wedge bond (B)</p> Signup and view all the answers

What type of molecule has a chiral center?

<p>A molecule with four different groups attached (A)</p> Signup and view all the answers

What defines a nucleophile?

<p>Electron-rich species often having a negative charge (B)</p> Signup and view all the answers

What does the term 'electron-poor' refer to?

<p>Electrophiles that attract electrons (B)</p> Signup and view all the answers

What primarily determines the distribution patterns of substituted products in free radical reactions?

<p>The stability of the intermediate radicals (C)</p> Signup and view all the answers

Which classification describes the mechanism involving the movement of two electrons in turn?

<p>Polar mechanism (B)</p> Signup and view all the answers

Which type of carbon radical is the most stable?

<p>Tertiary (3o) (D)</p> Signup and view all the answers

Which of the following best describes the function of curly arrows in reaction mechanisms?

<p>Show the movement of electrons (B)</p> Signup and view all the answers

What effect does hyperconjugation have on molecular stability?

<p>It increases stability by allowing electron interaction with adjacent orbitals (C)</p> Signup and view all the answers

How can alkenes function in a chemical reaction?

<p>As nucleophiles (D)</p> Signup and view all the answers

Which radicals are identified as being unusually stable due to resonance effects?

<p>Benzyl and allyl radicals (B)</p> Signup and view all the answers

What role do alkyl groups play in the stability of radicals?

<p>Alkyl groups are weakly electron donating due to hyperconjugation. (C)</p> Signup and view all the answers

What represents the energy difference between reactants and products in a chemical mechanism?

<p>Standard free energy change (B)</p> Signup and view all the answers

What is necessary for two radicals to form a bond?

<p>Each radical must donate one electron (D)</p> Signup and view all the answers

What characterizes the transition states in a chemical reaction mechanism?

<p>They are high energy peaks (B)</p> Signup and view all the answers

In radical mechanisms, what occurs during homolysis?

<p>Each atom involved receives one electron (B)</p> Signup and view all the answers

What does the activation energy represent in a chemical reaction pathway?

<p>The energy difference between reactants and the transition state (D)</p> Signup and view all the answers

Which of the following best describes a lone pair in the context of electron-rich centers?

<p>A pair of electrons not used in bonding (D)</p> Signup and view all the answers

What defines an electron poor center in a molecule?

<p>Presence of positively charged fragments (A)</p> Signup and view all the answers

Which statement accurately describes the structure of alkanes?

<p>They contain only single bonds between carbon atoms. (B)</p> Signup and view all the answers

What is the primary purpose of studying mechanisms in chemistry?

<p>To understand how reactants transform into products (D)</p> Signup and view all the answers

What is a significant feature of the bonding in alkanes?

<p>They possess weak London dispersion forces as the only intermolecular force. (C)</p> Signup and view all the answers

Which of the following is true about the reactivity of alkanes?

<p>They combust in a flame, producing CO2 and H2O. (D)</p> Signup and view all the answers

What is the general formula for alkanes?

<p>C_nH_{2n+2} (B)</p> Signup and view all the answers

Which step in the halogenation of alkanes is responsible for radical formation?

<p>Initiation (C)</p> Signup and view all the answers

What characterizes the reaction of alkanes during halogenation?

<p>Free radicals are involved in propagating the reaction. (D)</p> Signup and view all the answers

How does the boiling point of alkanes trend with increasing molecular weight?

<p>It generally increases with molecular weight and carbon chain length. (D)</p> Signup and view all the answers

What is a key feature of the chlorination process of alkanes?

<p>Chlorine radicals serve as chain carriers during the reaction. (A)</p> Signup and view all the answers

What determines the physical state of alkanes at standard conditions?

<p>The molecular weight and chain length of the alkane. (B)</p> Signup and view all the answers

Which functional groups are characteristic of the products formed from alkane reactions?

<p>Haloalkanes and alkenes (B)</p> Signup and view all the answers

In metabolic processes that involve chemical mechanisms, which factor significantly affects drug stability?

<p>The understanding of chemical reactions involved (D)</p> Signup and view all the answers

What is true about covalent inhibitors like Amoxycillin?

<p>They can form stable adducts with the targeted enzyme. (D)</p> Signup and view all the answers

What happens to the carbon of the lactam in the mechanism involving Amoxycillin?

<p>It is converted into an ester during the reaction. (B)</p> Signup and view all the answers

Which of the following compounds are classified as halogens that react with alkanes?

<p>Chlorine and bromine (A)</p> Signup and view all the answers

What is the significance of resonance structures in reaction mechanisms?

<p>They help visualize electron/charge delocalisation. (A)</p> Signup and view all the answers

Which of the following statements about resonance structures is true?

<p>They represent extreme possibilities of electron location. (C)</p> Signup and view all the answers

In the context of resonance, which factor decreases the stability of a resonance form?

<p>Charge separation. (A)</p> Signup and view all the answers

Which types of electrons can be moved when drawing resonance structures?

<p>Only π electrons and lone-pair electrons. (D)</p> Signup and view all the answers

Why must the atoms be in the same plane for resonance structures?

<p>To facilitate overlap of p orbitals. (D)</p> Signup and view all the answers

What is incorrect about the representation of resonance structures?

<p>They indicate equilibrium between different states. (A)</p> Signup and view all the answers

Which statement regarding the energy of a molecule based on its resonance forms is true?

<p>It is lower than that of the most stable resonance form. (C)</p> Signup and view all the answers

What factor does NOT contribute to the stability of a resonance structure?

<p>Charge separation. (D)</p> Signup and view all the answers

The stability of the intermediate radical is determined by the number of carbon atoms bonded to the carbon with the lone ______.

<p>electron</p> Signup and view all the answers

Hyperconjugation results from the interaction of electrons in a σ-bond with an adjacent unfilled p orbital or a ______ orbital.

<p>pi</p> Signup and view all the answers

A tertiary radical is characterized by having ______ carbon atoms bonded to the carbon with the lone electron.

<p>three</p> Signup and view all the answers

The benzyl and allyl radicals are more stable due to ______, which allows for the delocalization of electrons.

<p>resonance</p> Signup and view all the answers

The hyperconjugation effect means that alkyl groups are weakly electron ______.

<p>donating</p> Signup and view all the answers

Functional groups are important in pharmacy because they help to deduce the properties of drugs such as ______.

<p>ionisation</p> Signup and view all the answers

In this course, students will learn to identify the ______, electrophile, and leaving group in organic molecules.

<p>nucleophile</p> Signup and view all the answers

Curly arrows are used to signify bond making and ______ processes in reaction mechanisms.

<p>breaking</p> Signup and view all the answers

Radical stability can be explained through concepts like ______ and resonance stabilisation.

<p>hyperconjugation</p> Signup and view all the answers

Alkane chemistry will be a focal point of the lecture, particularly in understanding their ______.

<p>properties</p> Signup and view all the answers

Most drugs are simple organic molecules composed of two parts: a hydrocarbon part that is usually ______

<p>unreactive</p> Signup and view all the answers

The functional group (FG) is where most of the ______ of the molecule occur.

<p>reactions/interactions</p> Signup and view all the answers

Molecules with the same functional group generally have similar ______.

<p>properties</p> Signup and view all the answers

In pharmacology, understanding ______ properties is essential for making analytical choices.

<p>physiochemical</p> Signup and view all the answers

Functional groups contribute to the ______ reactivities of the molecules they are part of.

<p>characteristic</p> Signup and view all the answers

Sp3 hybridized carbon atoms adopt a ______ shape.

<p>tetrahedral</p> Signup and view all the answers

A nucleophile is an atom or molecule that has a pair of electrons to ______.

<p>share</p> Signup and view all the answers

An electrophile is also known as an 'electron-______' species.

<p>loving</p> Signup and view all the answers

The sequence of bond-making and bond-breaking steps in a chemical reaction is described by the ______.

<p>mechanism</p> Signup and view all the answers

A ______ center is a carbon atom with four different groups attached.

<p>chiral</p> Signup and view all the answers

Ionic and polar mechanisms involve the movement of ______ electrons in turn.

<p>two</p> Signup and view all the answers

In 3D molecular representation, a wedge indicates a bond pointing ______ us.

<p>towards</p> Signup and view all the answers

Typically, nucleophiles possess a negative charge or a ______ pair of electrons.

<p>lone</p> Signup and view all the answers

Resonance structures are used to describe electron/charge ______.

<p>delocalisation</p> Signup and view all the answers

Only ______ electrons and lone-pair electrons/radicals are moved in resonance structures.

<p>Ï€</p> Signup and view all the answers

Resonance forms are not ______ or different compounds.

<p>isomers</p> Signup and view all the answers

The most stable resonance form makes the greatest ______ to the overall structure.

<p>contribution</p> Signup and view all the answers

Atoms must be in the same ______ for resonance structures to be valid.

<p>plane</p> Signup and view all the answers

Only representations of the extreme possibilities of ______ location exist in resonance.

<p>electron</p> Signup and view all the answers

The energy of the molecule is less than any of the contributing ______.

<p>structures</p> Signup and view all the answers

Resonance structures only exist on ______.

<p>paper</p> Signup and view all the answers

Some drugs work by covalently binding to their biological ______

<p>target</p> Signup and view all the answers

Drug degradation processes occur via chemical ______

<p>reactions</p> Signup and view all the answers

Amoxycillin acts as an example of a covalent ______

<p>inhibitor</p> Signup and view all the answers

Alkanes are also known as ______

<p>paraffins</p> Signup and view all the answers

The general formula for alkanes is ______

<p>CnH2n+2</p> Signup and view all the answers

Alkanes generally burn in a flame producing ______, H2O and heat.

<p>CO2</p> Signup and view all the answers

Weak London dispersion forces are the only ______ forces at play between alkanes.

<p>intermolecular</p> Signup and view all the answers

Halogenation of alkanes proceeds via a ______ mechanism.

<p>radical</p> Signup and view all the answers

For alkanes, melting and boiling points generally increase with ______ weight.

<p>molecular</p> Signup and view all the answers

The formation of chlorine radicals occurs during the ______ step in radical mechanisms.

<p>initiation</p> Signup and view all the answers

In halogenation, one radical is used to generate another, a process referred to as ______.

<p>propagation</p> Signup and view all the answers

In the termination step of radical reactions, two radicals combine to produce a ______ species.

<p>neutral</p> Signup and view all the answers

London dispersion forces can create ______ dipoles that temporarily form in alkanes.

<p>temporary</p> Signup and view all the answers

Alkanes react poorly with ionic or polar ______.

<p>substances</p> Signup and view all the answers

Amoxycillin starts its action at an electron-rich ______.

<p>alcohol</p> Signup and view all the answers

Flashcards

Functional Group

A part of a molecule that defines its reactivity and overall properties. It's responsible for how the molecule interacts with other molecules.

ADME

The study of how drugs are absorbed, distributed throughout the body, metabolized, and excreted.

Absorption

The process by which a drug enters the bloodstream.

Distribution

How a drug is transported throughout the body to reach its target.

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Metabolism

The process of breaking down a drug into smaller metabolites in the body.

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Chiral Centre

A carbon atom bonded to four different groups, creating a non-superimposable mirror image.

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3D Representations

A three-dimensional representation of molecules. Wedge bonds point towards you, hashed bonds point away, and plain bonds are in the plane of the screen.

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Reaction Mechanism

A step-by-step description of how a reaction occurs, showing the movement of electrons and formation/breaking of bonds.

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Nucleophile

A chemical species that donates electrons to form a new bond. It is typically electron-rich and has a negative charge or lone pair.

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Electrophile

A chemical species that accepts electrons to form a new bond. It is typically electron-deficient and has a positive charge or partial positive charge.

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Ionic/Polar Reaction

A type of reaction where two electrons move together in a single step.

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Radical Reaction

A type of reaction where one electron moves at a time, creating free radicals.

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Free Radical

A chemical species with an unpaired electron, giving it high reactivity.

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Single-headed arrow

A single-headed arrow that shows the movement of one electron.

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Radical

A species with an unpaired electron, often denoted with a dot.

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Homolysis

The process of breaking a covalent bond by dividing the shared electrons equally.

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Transition state

A high-energy state that occurs during a reaction, where bonds are breaking and forming.

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Intermediate

A stable molecule or ion that is formed during a reaction, existing between the reactants and products.

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Activation energy

The energy required to reach the transition state, and therefore initiate the reaction.

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Energy profile diagram

A representation of the energy changes that occur throughout a reaction.

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Radical Stability

The stability of the intermediate radical formed during a reaction determines the distribution of products.

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Hyperconjugation

A type of chemical bond interaction where electrons from a sigma bond (single bond) are delocalized into an adjacent empty p orbital, stabilizing the molecule.

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Benzyl Radical

A radical with one unpaired electron on a carbon atom directly attached to a benzene ring. It's unusually stable due to resonance.

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Allyl Radical

A radical with one unpaired electron on a carbon atom directly attached to a double bond. It's unusually stable due to resonance.

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Resonance

Describes the delocalization of electrons within a molecule, where electrons are not confined to a single bond but can be shared across multiple atoms.

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Resonance Structures

Structures that show the possible arrangements of electrons in a molecule; not actual isomers, but rather representations of the extreme possibilities of electron location.

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Resonance Hybrid

A structure representing the average of all possible resonance structures, where the electrons are delocalized and do not have a definite position.

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Pi (Ï€) Bond

A type of covalent bond formed by the overlap of p orbitals, allowing electrons to delocalize across multiple atoms.

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Resonance Stabilization

Describes the stability of a molecule due to the delocalization of electrons through resonance, which helps to distribute charges and lower the overall energy of the molecule.

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Double-Headed Resonance Arrow

A special type of arrow used to show the movement of electrons in resonance structures, indicating that different contributing forms are possible but only one actual structure exists.

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Major Resonance Contributor

A resonance structure that contributes more to the overall structure of the molecule than others, usually the one with the most covalent bonds and minimal charge separation.

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Minor Resonance Contributor

A resonance structure that contributes less to the overall structure of the molecule, usually the one with fewer covalent bonds and more charge separation.

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Alkanes

A chemical compound containing only carbon and hydrogen atoms joined by single bonds. They are saturated hydrocarbons, meaning they have no double or triple bonds.

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Oxidation

The process of breaking down a molecule into smaller parts, often through the addition of oxygen or other atoms.

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Reduction

The process of adding electrons to a molecule, often by removing oxygen or other atoms.

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Drug Target

The point at which a drug interacts with its target molecule to exert its effect. It can be a specific receptor, enzyme, or other cellular component.

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Inhibitor

A type of drug that binds to a specific receptor or enzyme and prevents it from working, effectively stopping the cellular process.

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Covalent Inhibitor

A type of inhibitor where the drug forms a strong, irreversible covalent bond with its target, permanently inactivating it.

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Metabolic Stability

The tendency of a molecule to resist degradation or breakdown, especially when exposed to various chemical environments.

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Excretion

The process by which a drug is eliminated from the body, typically through urine, feces, or breath. It's the way the body gets rid of the drug.

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Pharmacokinetics

The change in the concentration of a drug over time. It's a measure of how quickly the drug is absorbed, distributed, metabolized, and excreted.

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Pharmacodynamics

The effect of a drug on the body, including its therapeutic effects and potential side effects.

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Medicinal Chemistry

The study of the chemical processes involved in the synthesis, metabolism, and degradation of drugs.

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Curly Arrows

The movement of electrons in a chemical reaction, shown by curly arrows. A single-headed arrow indicates the movement of one electron, while a double-headed arrow indicates two electrons moving together.

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Drug Administration

The process of administering a drug into the body (e.g., swallowing a pill, injection, etc.)

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What are Resonance Structures?

Resonance structures are different ways of representing the electron distribution within a molecule, showing how electrons can be delocalized across multiple atoms. They are not real isomers, but rather extreme possibilities of where the electrons might be located.

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What is Resonance used for?

Resonance structures are used to describe the delocalization of electrons in a molecule. This delocalization helps to stabilize the molecule by distributing the charge and energy across multiple atoms.

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What atoms can't participate in resonance?

Sp3 hybridized atoms don't participate in resonance because they lack the necessary p-orbitals for electron delocalization. Only π electrons and lone-pair electrons can be moved in resonance structures.

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What is a Resonance Hybrid?

The resonance hybrid is a representation of the actual molecule, where the electrons are not in a fixed position, but rather delocalized across multiple atoms. It is essentially an average of all the possible resonance structures.

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What makes a resonance structure more stable?

The more covalent bonds a resonance structure has, the more stable it is. The more covalent bonds, the more the electrons are shared amongst atoms, resulting in a lower energy state.

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How does resonance impact the energy of a molecule?

The energy of the actual molecule is lower than any of the contributing resonance structures due to electron delocalization. The most stable resonance form makes the greatest contribution to the hybrid structure.

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What condition is necessary for resonance to occur?

Resonance structures can only be drawn if the atoms involved are in the same plane. This is because p-orbital overlap is required for electron delocalization.

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What does a double-headed resonance arrow represent?

A double-headed resonance arrow is used to indicate that the structures are resonance forms, meaning they are different representations of the same molecule, not separate isomers.

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What is a covalent inhibitor?

A covalent inhibitor binds permanently to its target molecule, preventing it from working.

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How does amoxycillin work?

Amoxycillin is an example of a covalent inhibitor that binds to the active site of an enzyme involved in bacterial cell wall synthesis.

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What are the key steps in amoxycillin's binding mechanism?

The reaction starts with an electron-rich alcohol (Serine) in the enzyme, and electrons move towards an electron-poor carbon atom (lactam) in the drug.

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What happens to amoxycillin after it binds to the enzyme?

The lactam ring in amoxycillin converts into an ester and a secondary amine. This ester is stable and doesn't break down easily.

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What is an alkane?

Alkanes are saturated hydrocarbons, containing only single bonds between carbon and hydrogen atoms.

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What are the key characteristics of alkanes?

General formula: CnH2n+2. They are very unreactive due to strong sigma bonds.

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Where do we find alkanes and what are they used for?

Alkanes are found in petroleum and are separated by distillation. They are used as fuels and raw materials for plastics.

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What happens when alkanes burn?

Alkanes undergo combustion reactions, burning in air to produce carbon dioxide, water, and heat.

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How do alkanes react with halogens?

Alkanes can react with chlorine or bromine in a radical mechanism, which involves three steps: initiation, propagation, and termination.

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What happens in the initiation step of alkane halogenation?

The initiation step involves the formation of chlorine radicals due to the absorption of light energy.

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Explain the propagation step in alkane halogenation.

The propagation step generates more radicals, where a chlorine radical abstracts a hydrogen atom from the alkane, forming a methyl radical.

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What happens in the termination step of alkane halogenation?

The termination step involves the combination of two radicals to form a neutral species.

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How does radical stability influence the products of a halogenation reaction?

The stability of a radical determines the products formed in a reaction. More stable radicals form in greater amounts.

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What is hyperconjugation in radicals?

Hyperconjugation is the delocalization of electrons from a sigma bond into an adjacent empty p-orbital, stabilizing the radical.

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What is a benzyl radical and why is it stable?

A benzyl radical is a carbon radical attached to a benzene ring - it's unusually stable due to resonance.

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What is an allyl radical and why is it stable?

An allyl radical is a carbon radical attached to a double bond - it's unusually stable due to resonance and hyperconjugation.

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Study Notes

PHA111 Functional Group Chemistry 1

  • The course covers functional group chemistry, important for pharmacy students.
  • Learning objectives include appreciating the importance of functional group chemistry, defining mechanistic terminologies for reaction mechanisms, identifying nucleophiles, electrophiles, and leaving groups in organic molecules, identifying functional groups in drug molecules, understanding the use of curly arrows for bond making/breaking processes, and explaining product distribution patterns.
  • Functional group chemistry enables understanding chemical structure, deducing properties of drugs, such as ionization, solubility (lipid vs. aqueous), and ADME (Absorption, Distribution, Metabolism, Excretion).
  • Functional groups are crucial for understanding receptor binding, therapeutic effects, designing medicines, and understanding physiochemical properties affecting analytical choices.
  • Drugs are typically composed of a hydrocarbon part (unreactive) and a functional group (where most reactions occur). These functional groups impart similar properties.
  • Chemical similarity in drugs is explored, exemplified by examples of molecules that could cause extreme bronchospasm.
  • Different types of hydrocarbon compounds (e.g., alkanes, alkenes, alkynes, alcohols) and their functional groups within such structures are described, which are crucial to knowing.
  • Key concepts of 3D representations, focusing specifically on sp³ hybridized carbon atoms and chiral centers.
  • Types of reaction mechanisms are defined, such as ionic/polar mechanisms where two electrons move, and radical mechanisms where one electron moves.
  • The lecture defines and discusses nucleophiles (electron-rich, often negatively charged) and electrophiles (electron-poor, often positively charged) while also exploring their properties.
  • Understanding leaving groups helps explain displacement reactions as part of mechanisms.
  • The terms heterolysis and homolysis, which describe different bond breaking mechanisms, are defined.
  • The use of curly arrows in reaction mechanisms emphasizing the importance of correct arrow placement are outlined, with a clear distinction between polar and radical mechanisms.
  • Transition states and intermediates in chemical reactions are discussed.
  • The importance of mechanisms regarding drug action in various biological processes and drug stability are highlighted. Case studies of penicillin-based drug reactivity are given.
  • Properties and reactivity of alkanes, including combustion and halogenation are detailed.
  • Radical reactions in halogenation have three distinct steps: initiation, propagation, and termination.
  • The stability of radicals, including hyperconjugation and resonance structures, are explained.
  • Different types of resonance structures will be understood and drawn.
  • The effect of oxidation on drugs, namely auto-oxidation, is illustrated (radical process linked to drug degradation and drug stability. Specific examples include auto-oxidation processes leading to drug degradation under light, heat, and presence of metal ions including peroxidative mechanisms.

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