Functional Groups 1

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Questions and Answers

Which cyclic alkane behaves more like an unsaturated molecule?

  • Cyclopentane
  • Cyclopropane (correct)
  • Cyclohexane
  • Cyclobutane

What is the consequence of the electron delocalization in conjugated alkenes?

  • Decreased reactivity of the alkene
  • Generation of a mixture of products (correct)
  • Formation of a single product
  • Increase in the stability of the compound

What structural feature is characteristic of alkyl halides?

  • Presence of alkenes
  • R-X bond where R is an alkyl group and X is a halogen (correct)
  • Formation of strong hydrogen bonds with water
  • Cyclic structure with multiple bonds

Why are alkyl halides typically insoluble in water?

<p>Weak van der Waals forces between molecules (A)</p> Signup and view all the answers

Which factor significantly affects the stability of carbocations?

<p>Hybridization of the carbon atom (D)</p> Signup and view all the answers

What storage precaution should be taken with alkenes?

<p>Store in well-sealed containers to prevent peroxide formation (B)</p> Signup and view all the answers

What is a common result of nucleophilic substitution reactions involving alkyl halides?

<p>Replacement of the halogen atom by a nucleophile (C)</p> Signup and view all the answers

Which cyclic alkane is known for having similar stability/reactivity to open-chain alkanes?

<p>Cyclopentane (C), Cyclohexane (D)</p> Signup and view all the answers

What type of substitution reaction occurs when the reaction rate depends only on the concentration of the substrate?

<p>SN1 reaction (D)</p> Signup and view all the answers

Which alkyl halide structure is more likely to undergo nucleophilic substitution through an SN1 mechanism?

<p>Tertiary alkyl halide (A)</p> Signup and view all the answers

What is the result when a nucleophile attacks a tertiary alkyl halide from either side?

<p>Formation of enantiomers (A)</p> Signup and view all the answers

What happens to the configuration of the central carbon atom during an SN2 reaction?

<p>It gets inverted (A)</p> Signup and view all the answers

Which functional group is produced from the nucleophilic substitution with hydroxide (OH)?

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

What is indicated by the polar nature of the C-X bond in alkyl halides?

<p>Partial charges are formed (A)</p> Signup and view all the answers

Which condition is essential for an SN2 reaction to occur?

<p>The presence of a primary or secondary substrate (D)</p> Signup and view all the answers

Which of the following compounds is commonly used as a solvent in organic reactions?

<p>Chloroform (CHCl3) (D)</p> Signup and view all the answers

What is the primary reason that nucleophilic substitution reactions can occur with various functional groups?

<p>Many functional groups can act as either a nucleophile or a leaving group. (C)</p> Signup and view all the answers

How do conjugated systems influence the reactivity of a molecule compared to isolated π bonds?

<p>Conjugated π bonds make a molecule less reactive and more stable. (D)</p> Signup and view all the answers

What can be concluded about the stability of alkenes compared to alkyl halides?

<p>Alkenes are generally more reactive than alkyl halides. (D)</p> Signup and view all the answers

What characterizes the leaving group in a nucleophilic substitution reaction?

<p>It is the atom or group that is replaced in the reaction. (B)</p> Signup and view all the answers

Which statement correctly describes the UV absorption of conjugated systems?

<p>The absorption of UV light is proportional to the extent of conjugation. (C)</p> Signup and view all the answers

What is a significant factor contributing to the color of compounds like β-Carotene?

<p>Extended systems of conjugation allow UV absorptions to reach the visible spectrum. (D)</p> Signup and view all the answers

Why might elimination reactions compete with nucleophilic substitution reactions?

<p>Both involve the use of bases and result in different products. (B)</p> Signup and view all the answers

Which statement is true regarding the stability of alkyl halides in air?

<p>Chloroform is an alkyl halide that can form a toxic compound when exposed. (D)</p> Signup and view all the answers

What role does water play in the formation of alcohol during the hydration of propene?

<p>Water acts as a nucleophile, providing electrons that facilitate the formation of an alcohol after losing H+.</p> Signup and view all the answers

Explain the stability of carbocations and how it affects their formation.

<p>Carbocations are more stable with increasing substitution; tertiary carbocations are the most stable and easiest to form, while primary are the least stable.</p> Signup and view all the answers

Describe the reactivity of epoxides and their behavior when protonated.

<p>Epoxides are highly reactive due to their strained structure and become protonated when exposed to H+, making them susceptible to nucleophilic attack.</p> Signup and view all the answers

What are peroxides and why are they considered unstable?

<p>Peroxides are compounds with a O-O bond that are often unstable and can be explosive due to the weak nature of this bond.</p> Signup and view all the answers

How does the formation of carbocations differ in hydration compared to nucleophilic substitution reactions?

<p>In hydration, carbocation formation is a key intermediate for alcohol synthesis, while in nucleophilic substitution, carbocations can also be intermediates but vary in stability based on substrate structure.</p> Signup and view all the answers

What is the general formula for alkanes and what does it signify?

<p>The general formula for alkanes is $CnH_{2n+2}$, indicating that for every $n$ carbon atoms, there are $2n+2$ hydrogen atoms.</p> Signup and view all the answers

Why are alkanes considered to be non-polar and how does it affect their solubility?

<p>Alkanes are non-polar because they contain only non-polar C-C and C-H bonds, making them insoluble in water but soluble in other non-polar substances.</p> Signup and view all the answers

Describe the stability and reactivity of alkanes.

<p>Alkanes are very stable and inert due to their non-polar bonds, showing little reactivity under normal conditions.</p> Signup and view all the answers

Define primary (1º) and secondary (2º) alkyl groups with examples.

<p>A primary alkyl group has one carbon replacing a hydrogen, such as $CH_3CH_2$; a secondary alkyl group has two carbons replacing two hydrogens, like $(CH_3)_2CH$.</p> Signup and view all the answers

How do the physical properties of alkanes change as the number of carbon atoms increases?

<p>As the number of carbon atoms increases, alkanes transition from gases to liquids due to increased van der Waals interactions.</p> Signup and view all the answers

Explain why alkanes are often classified as lipids.

<p>Alkanes are classified as lipids because they are insoluble in water but soluble in non-polar solvents, similar characteristics to fats and oils.</p> Signup and view all the answers

What role does bond polarity play in the reactivity of organic molecules, particularly alkanes?

<p>Bond polarity affects the physical properties and reactivity of organic molecules; for alkanes, the non-polar bonds result in their reduced chemical reactivity.</p> Signup and view all the answers

How do the solubility characteristics of alkanes impact their behavior in biological systems?

<p>Alkanes' insolubility in water means they can pass through biological membranes and enter lipid materials, which is essential for drug delivery.</p> Signup and view all the answers

What distinguishes alkenes from alkanes in terms of molecular structure?

<p>Alkenes contain at least one double bond, while alkanes only have single bonds.</p> Signup and view all the answers

Explain why low molecular mass alkenes exist as gases at room temperature.

<p>Low molecular mass alkenes have weak van der Waals interactions and lack polar bonds, resulting in gaseous states.</p> Signup and view all the answers

What role do acid catalysts play in hydration reactions of alkenes?

<p>Acid catalysts act as electrophiles, facilitating the addition of water to the double bond in alkenes.</p> Signup and view all the answers

Describe the solubility of alkenes in water and explain why.

<p>Alkenes are insoluble in water due to their non-polar nature and inability to form hydrogen bonds.</p> Signup and view all the answers

What is a primary characteristic of the addition reaction involving alkenes?

<p>The primary characteristic is the conversion of the double bond into single bonds, resulting in a saturated hydrocarbon.</p> Signup and view all the answers

Identify how the physical properties of alkenes relate to their molecular structure.

<p>The absence of polar bonds in alkenes results in weak intermolecular forces, affecting their physical states.</p> Signup and view all the answers

What effect does the presence of double bonds have on the reactivity of alkenes?

<p>Double bonds increase the reactivity of alkenes, making them more prone to addition reactions.</p> Signup and view all the answers

Explain the difference between isolated and conjugated double bonds in alkenes.

<p>Isolated double bonds are separated by single bonds, while conjugated double bonds are alternating with single bonds.</p> Signup and view all the answers

What is the effect of the polar nature of the C-X bond in alkyl halides on their reactivity?

<p>The polar C-X bond creates partial charges, allowing the δ+ carbon to attract nucleophiles, which facilitates nucleophilic substitution reactions.</p> Signup and view all the answers

Describe the difference in nucleophilic substitution reactions between 1° and 3° alkyl halides.

<p>1° alkyl halides typically undergo SN2 reactions with a transition state, while 3° alkyl halides undergo SN1 reactions through ionization, forming a more stable carbocation first.</p> Signup and view all the answers

What influences the outcome of a nucleophilic substitution reaction when using different nucleophiles?

<p>The type of nucleophile determines the functional group formed; for example, hydroxide (OH) produces an alcohol, while OCH3 yields an ether.</p> Signup and view all the answers

What structural characteristic leads to the formation of mirror image products in certain nucleophilic substitution reactions?

<p>When the central carbon atom in a 3° haloalkane is bonded to four different groups, it creates chiral centers that produce enantiomers upon nucleophilic attack.</p> Signup and view all the answers

Why is the configuration of the central carbon atom inverted during an SN2 reaction?

<p>In an SN2 reaction, the nucleophile attacks the carbon from the opposite side of the leaving group, resulting in the inversion of stereochemistry.</p> Signup and view all the answers

Explain how the reactivity of alkyl halides is related to their type of substitution reaction.

<p>The reactivity of alkyl halides varies by structure: 3° undergo SN1 due to stable carbocations, while 1° and 2° undergo SN2 due to the formation of a transition state.</p> Signup and view all the answers

How does the stability of carbocations affect their formation during nucleophilic substitution reactions?

<p>More stable carbocations (like 3°) form more readily during SN1 reactions, while less stable carbocations (1° and 2°) will involve transition states in SN2 reactions.</p> Signup and view all the answers

What is one consequence of the interaction between drugs and their enantiomers during nucleophilic substitution reactions?

<p>One enantiomer may be active while the other is inactive or toxic, highlighting the significance of chirality in drug efficacy and safety.</p> Signup and view all the answers

What is the main reason for the formation of a mixture of products when butadiene reacts with an A-B addition?

<p>The delocalization of electrons leads to different possible positions for the addition, resulting in multiple products.</p> Signup and view all the answers

Why does cyclopropane behave more like an unsaturated molecule compared to other cycloalkanes?

<p>Cyclopropane has significant angle strain and torsional strain, making it less stable and more reactive, akin to unsaturated compounds.</p> Signup and view all the answers

How do the physical properties of alkyl halides relate to their bonding characteristics?

<p>Alkyl halides have polar C-X bonds but only weak van der Waals interactions, resulting in low RMM alkyl halides being gases or liquids at room temperature.</p> Signup and view all the answers

What storage precautions should be taken to prevent the formation of peroxides with alkenes?

<p>Alkenes should be stored in well-sealed containers to minimize exposure to air and light, which can lead to peroxide formation.</p> Signup and view all the answers

Describe the solubility of alkyl halides in water and explain why this occurs.

<p>Alkyl halides are insoluble in water due to their inability to form significant hydrogen bonds with water molecules.</p> Signup and view all the answers

Discuss how reactivity in conjugated alkenes is influenced by electron delocalization.

<p>Electron delocalization in conjugated alkenes stabilizes the molecule, yet it can also create multiple reactive sites that lead to varied product formation.</p> Signup and view all the answers

What role does the general structure R-X play in the properties of alkyl halides?

<p>The structure R-X defines the nature of the alkyl halide, influencing its reactivity, polarity, and boiling points based on the alkyl group and the halogen used.</p> Signup and view all the answers

How does the stability of cyclic alkanes compare to that of open-chain alkanes?

<p>Cyclic alkanes generally exhibit similar stability and reactivity to open-chain alkanes, with cyclopropane being an important exception due to its strain.</p> Signup and view all the answers

What distinguishes conjugated dienes from isolated dienes in terms of their p orbital overlap?

<p>Conjugated dienes have adjacent p orbitals that can overlap, allowing for delocalization of π electrons, whereas isolated dienes have p orbitals that do not overlap.</p> Signup and view all the answers

How does the extent of conjugation in a molecule affect its UV absorption?

<p>Increased conjugation results in lower energy absorption and longer wavelengths in the UV spectrum.</p> Signup and view all the answers

What role do leaving groups play in nucleophilic substitution reactions?

<p>Leaving groups are atoms or groups that depart from the substrate, facilitating the substitution of nucleophiles.</p> Signup and view all the answers

Why are alkyl halides often used as solvents in organic reactions?

<p>Alkyl halides are relatively stable in air and can dissolve a variety of organic compounds, making them suitable solvents.</p> Signup and view all the answers

What is the relationship between the structure of colored compounds and their conjugated systems?

<p>Colored compounds typically have extended conjugated systems that allow UV absorption to extend into the visible spectrum.</p> Signup and view all the answers

How do elimination reactions compete with nucleophilic substitution reactions?

<p>Both reactions can occur when heat is applied with bases for elimination, but ranging nucleophiles may promote substitution instead.</p> Signup and view all the answers

What factor contributes to the stability of molecules with conjugated π bonds compared to those with isolated π bonds?

<p>Molecules with conjugated π bonds are more stable due to the delocalization of electrons across multiple p orbitals.</p> Signup and view all the answers

In what way does irradiation with UV light affect conjugated molecules?

<p>Irradiation promotes π electrons from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO).</p> Signup and view all the answers

Flashcards

Nucleophilic substitution reaction

A reaction where a nucleophile replaces a leaving group on a molecule.

Elimination reaction

A reaction that forms a double bond by losing atoms/groups.

Conjugated dienes

Multiple double bonds with overlapping p-orbitals.

Isolated dienes

Multiple double bonds with non-overlapping p-orbitals.

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Conjugation

Alternating single and multiple bonds, allowing p-orbital overlap.

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UV Spectroscopy

Using UV light to identify conjugated systems by measuring absorption.

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HOMO

Highest Occupied Molecular Orbital.

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LUMO

Lowest Unoccupied Molecular Orbital

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Conjugated Alkene Reactivity

Conjugated alkenes react with electrophiles in a way that leads to multiple products, instead of just one. This happens because the electrons are "delocalized" across multiple carbon atoms, making the reaction sites less specific.

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Cycloalkanes vs. Alkanes

Cycloalkanes are cyclic versions of alkanes, meaning they form rings. Most cycloalkanes behave similarly to alkanes in terms of stability and reactivity. However, cyclopropane is an exception.

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Cyclopropane Reactivity

Cyclopropane, unlike other cycloalkanes, behaves more like an unsaturated molecule. It's more reactive due to its strained ring structure

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Alkyl Halides: General Structure

Alkyl halides are organic compounds with a halogen atom (like chlorine, bromine, or fluorine) bonded to a carbon atom in an alkyl group.

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Alkyl Halide Physical Properties

Alkyl halides have weak van der Waals forces between molecules due to the polar carbon-halogen bond. This results in low boiling points, making smaller alkyl halides gases or liquids at room temperature.

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Alkyl Halide Solubility

Alkyl halides are generally insoluble in water. The reason is their inability to form strong interactions (like hydrogen bonding) with water molecules.

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Storing Alkenes

Alkenes are prone to forming peroxides, which can be dangerous. Therefore, they should be stored in well-sealed containers to prevent exposure to oxygen.

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Nucleophile

A species with an electron pair that can attack an electron-deficient atom, usually a carbon with a partial positive charge.

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Peroxide Formation

Peroxides form when alkenes react with oxygen. They can be explosive and should be handled with care. Proper storage helps prevent their formation.

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SN1 reaction

A nucleophilic substitution reaction with a 3° alkyl halide that proceeds through a carbocation intermediate. The rate depends only on the alkyl halide concentration.

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Carbocation

A positively charged carbon atom with only 3 bonds and an empty p orbital. Tertiary carbocations are the most stable.

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SN2 reaction

A nucleophilic substitution reaction with 1° or 2° alkyl halide that proceeds through a transition state. The rate depends on both the substrate and nucleophile concentrations.

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Stereochemistry in SN2

The nucleophile attacks from the opposite side of the leaving group in an SN2 reaction, inverting the configuration of the carbon atom.

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Biological activity and stereochemistry

Enantiomers of a drug often have different biological activities due to their different interactions with target molecules.

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Alkyl Group

An alkyl group is a branched or unbranched chain of carbon atoms, often represented by the symbol 'R'. It forms the basic structure of many organic molecules.

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Primary (1º) Alkyl Group

A primary alkyl group has one carbon atom directly attached to the main chain.

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Secondary (2º) Alkyl Group

A secondary alkyl group has two carbon atoms directly attached to the main chain.

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Alkane Structure

Alkanes are hydrocarbons with only single bonds between carbon atoms. Their general formula is CnH2n+2, where 'n' represents the number of carbon atoms.

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Alkane Properties

Alkanes are non-polar molecules due to the similar electronegativity of carbon and hydrogen. This results in weak intermolecular forces, leading to low boiling points and insolubility in water.

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Alkane Reactivity

Alkanes are very stable and unreactive due to the strong C-H and C-C bonds. They are often called 'paraffins', meaning 'little affinity' in Latin.

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Lipid Solubility of Alkanes

Alkanes are soluble in lipids (fats and oils) due to their non-polar nature. This allows them to cross cell membranes and enter the brain.

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Alkanes and Anesthetics

Some alkanes can be used as general anesthetics because their lipid solubility allows them to easily pass through cell membranes and reach the brain.

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Carbocation Stability

Carbocations, positively charged carbons, have varying stabilities. Tertiary (3°) carbocations are most stable, followed by secondary (2°), then primary (1°).

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How do we form an epoxide?

Epoxides form through oxidation, adding an oxygen atom across a double bond. This process is common in biochemical pathways.

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Epoxide Reactivity

Epoxides are highly reactive due to ring strain. They are easily protonated and then readily attacked by nucleophiles.

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What makes peroxides dangerous?

Peroxides are notoriously unstable due to the weak oxygen-oxygen bond. This makes them prone to decomposition, which can be explosive.

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Alkene general formula

The general formula for alkenes is CnH2n, indicating the presence of a double bond.

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Alkene physical properties

Alkenes are nonpolar molecules with weak intermolecular forces. Low molecular weight alkenes are gases, while higher molecular weight alkenes are liquids.

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Alkene solubility

Alkenes are insoluble in water due to their nonpolar nature. They dissolve in nonpolar solvents like lipids (fats and oils).

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Alkene addition reaction

In an addition reaction, a molecule breaks apart, and its pieces add across the double bond of an alkene, forming a single bond.

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Alkene hydrogenation

Hydrogenation is the addition of hydrogen (H2) across the double bond of an alkene, converting it to an alkane. This process saturates the molecule.

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Alkene hydration

Hydration is the addition of water (H2O) across the double bond of an alkene, forming an alcohol. This reaction requires an acid catalyst.

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Alkene storage

Alkenes should be stored in sealed containers to prevent exposure to oxygen, which can lead to the formation of explosive peroxides.

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Why Conjugated Alkenes React Differently?

Conjugated alkenes contain alternating single and double bonds, creating delocalized electrons. This delocalization leads to multiple products when they react with electrophiles, unlike regular alkenes.

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What are Cycloalkanes?

Cycloalkanes are cyclic versions of alkanes, meaning they form rings. Most cycloalkanes behave similarly to alkanes in terms of stability and reactivity.

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Is Cyclopropane Different?

Cyclopropane, unlike other cycloalkanes, behaves more like an unsaturated molecule. It's more reactive due to its strained ring structure.

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Alkyl Halides: The Basics

Alkyl halides are organic compounds with a halogen atom (like chlorine, bromine, or fluorine) bonded to a carbon atom in an alkyl group.

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Why Are Alkyl Halides Insoluble in Water?

Alkyl halides are generally insoluble in water. The reason is their inability to form strong interactions (like hydrogen bonding) with water molecules.

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Why Store Alkenes Carefully?

Alkenes are prone to forming peroxides, which can be dangerous. Therefore, they should be stored in well-sealed containers to prevent exposure to oxygen.

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Why Can't You Just Store Alkenes Any Way?

Peroxide formation is a serious concern because peroxides are unstable and can decompose explosively.

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Leaving Group

The atom or group that is replaced in a nucleophilic substitution reaction.

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Competing Reactions

Nucleophilic substitution and elimination reactions compete because both involve nucleophiles with unshared electron pairs.

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Polar C-X Bond

The C-X bond in alkyl halides is polar, meaning it has a partial positive charge on the carbon and a partial negative charge on the halogen.

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Conjugated System

A molecule with alternating single and double bonds where all adjacent p orbitals can overlap.

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HOMO & LUMO

HOMO: Highest Occupied Molecular Orbital; LUMO: Lowest Unoccupied Molecular Orbital. These orbitals are involved in UV absorption.

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SN2 Stereochemistry

The nucleophile attacks from the opposite side of the leaving group in an SN2 reaction, causing an inversion of configuration at the carbon atom.

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Color & Conjugation

Colored compounds have extended systems of conjugation, meaning their UV absorptions extend into the visible region.

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Enantiomers and Biological Activity

Enantiomers, mirror-image molecules, can have significantly different biological activities because they interact with target molecules in different ways.

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Stability & Conjugation

Molecules with conjugated π bonds tend to be more stable and less reactive than those with isolated π bonds.

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Alkyl Halides: Synthesis & Solvent

Alkyl halides are useful for synthesizing other functional groups and as solvents.

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3° Carbocation Formation

Tertiary alkyl halides (R3CX) readily form stable carbocations due to the electron-donating effect of the three alkyl groups, which stabilizes the positive charge.

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Study Notes

Organic Functional Groups

  • The majority of drugs are organic molecules.
  • These molecules can be small and simple, or large and complex.
  • They differ in their functionality due to different functional groups attached to a basic organic structure.
  • Functional groups are essential for drug properties and interactions with target molecules.

General Features of Molecules

  • Understanding reactivity (stability), physical properties (e.g., solubility), and interactions with targets in the body are important.

Bond Polarity

  • Bonds between atoms with differing electronegativity are polar.
  • Electron pairs in the bond move towards the more electronegative atom.
  • This creates a dipole in the bond.
  • C-H bonds are typically nonpolar.
  • C-O and C-halogen bonds are polar.
  • Polarisation in one bond can influence polarity in adjacent bonds (e.g., in chloroethane).
  • The inductive effect describes how polarity is transmitted through σ bonds.

Alkyl Groups

  • R represents an alkyl group.
  • Methyl (CH3) is the simplest alkyl group.
  • Alkyl groups can replace one or more H atoms in other alkyl groups.
  • Primary (1°) alkyl groups have one alkyl group attached to a single carbon atom.
  • Secondary (2°) alkyl groups have two alkyl groups attached to a single carbon atom.
  • Tertiary (3°) alkyl groups have three alkyl groups attached to a single carbon atom.

Alkanes

  • General formula: CnH2n+2
  • Alkanes consist of only nonpolar C-C and C-H bonds.
  • They are very stable and inert (also called paraffins).
  • Low molecular weight alkanes (1-4 carbons) are gases at room temperature.
  • Higher molecular weight alkanes are liquids.
  • Alkanes are insoluble in water but soluble in lipids.
  • They are stored safely in various conditions of light, heat, moisture, and air.

Alkenes

  • General formula: CnH2n
  • Alkenes contain a carbon-carbon double bond.
  • They are often referred to as unsaturated hydrocarbons.
  • Alkenes can have isolated or conjugated double bonds.
  • Alkenes are less reactive than alkanes but more reactive than alkanes.
  • They can undergo addition reactions.

Solubility of Alkenes

  • Alkenes are insoluble in water.
  • Alkenes are soluble in other nonpolar molecules like lipids (e.g., alkanes, fats, and oils).

Reactivity and Stability of Alkenes

  • Alkenes are similar to alkanes in their physical properties but differ in reactivity.
  • The double bond is the reactive functional group.
  • Addition reactions are characteristic of alkenes.
  • Hydration reactions involve adding water to the double bond.
  • Hydration reactions require an acid catalyst.
  • Addition reactions involve the introduction of a molecule to an alkene.

Mechanism

  • The mechanism of the hydration reaction involves the acid catalyst.
  • Carbocation formation involves a step where a carbon atom with a positive charge is formed.
  • The stability of the carbocation determines whether a specific reaction will occur.
  • The hydration of propene involves the formation of carbocations, and the most stable carbocation is favored in the reaction.

Oxidations

  • One type of oxidation is epoxide formation.
  • Epoxides are very reactive.
  • Epoxides can become protonated and then attacked by nucleophiles.
  • Oxidation reactions can also lead to peroxide formation.
  • Peroxides are unstable and can be explosive.

Conjugated Alkenes

  • Conjugated alkenes have multiple double bonds where the p orbitals can overlap.
  • This delocalization of electrons stabilizes the molecule.
  • Conjugated alkenes tend to be more stable and less reactive than those with isolated double bonds.

UV Spectroscopy

  • UV spectroscopy is a method used to determine the structure of conjugated molecules.
  • When a conjugated molecule is exposed to UV light, energy absorption takes place and electron promotion occurs from the Highest Occupied Molecular Orbital (HOMO) to the Lowest Unoccupied Molecular Orbital (LUMO).
  • More extensive conjugation leads to less energy required for absorption.

Alkyl Halides

  • General structure: R-X
  • Alkyl halides have a polar bond between the carbon atom and the halogen but overall have weak van der waals bonds.
  • Alkyl halides are gases or liquids at room temperature.
  • They are insoluble in water but soluble in other nonpolar solvents.
  • They are relatively stable.
  • They are involved in nucleophilic substitution reactions to form other functional groups.

Nucleophilic Substitution Reactions

  • Alkyl halides commonly undergo nucleophilic substitution reactions.
  • The substituted atom or group is a leaving group.
  • Other functional groups also undergo these reactions.
  • The rate of nucleophilic substitution may depend on the substrate and nucleophile concentration.

Elimination Reactions

  • Heating alkyl halides with bases can lead to elimination reactions, producing alkenes.
  • Nucleophiles, having unbonded electron pairs, often compete in reactions with nucleophilic substitution reactions.

Storage

  • Alkyl halides are typically stable in air.
  • Chloroform can, under certain conditions, form phosgene, a toxic compound.

Conjugation

  • Conjugated systems of double bonds enhance compound reactivity.
  • Conjugated systems have 2 or more double bonds, and have overlapping p orbitals.
  • Conjugated double bonds in conjugated systems are more stable than those in isolated systems.
  • 1,4-pentadiene has isolated double bonds while 1,3-pentadiene has conjugated double bonds.

Cycloalkanes

  • Cycloalkanes share the same formula as alkenes, CnH2n.
  • Cycloalkanes are cyclic derivatives of alkanes.
  • Cycloalkanes behave like open-chain alkanes in terms of stability/reactivity, with the exception of cyclopropane.
  • Cyclopropane is more akin to an unsaturated molecule.

Additional Notes

  • The stability of carbocations is related to the degree of alkyl substitution.
  • More substituted carbocations are more stable than less substituted ones, and the most stable ones are tertiary.
  • SN1 reactions involve a carbocation intermediate, with the rate depending only on the substrate concentration (alkyl halide).
  • SN2 reactions involve a transition state, with the rate depending on both substrate and nucleophile concentrations.
  • The configuration of the carbon involved in the reaction is inverted in an SN2 reaction.

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