Chemical Reactions: Substitution & Mechanisms

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Questions and Answers

For every photon of light absorbed, thousands of ______ molecules are formed.

chloromethane

Inhibitors, such as ______, slow down the reaction.

oxygen

The reaction of a carboxylic acid with an alcohol produces an ______.

ester

The process described for soap-making is referred to as ______.

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

An addition reaction occurs when two or more molecules react to form a single ______.

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

In the hydrogenation of vegetable oils, the geometry changes from ______ to tetrahedral bonds.

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

The Br2 molecule undergoes ______ fission to split into ions.

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

The ______ ion is formed when a Br~+~ attacks the C=C double bond.

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

A substitution reaction is a chemical reaction in which an atom or a group of atoms in a molecule is replaced by another atom or group at atoms, often involving ______.

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

The overall reaction of the halogenation of alkanes requires the presence of ______ light.

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

In the mechanism of monochlorination of methane, a chlorine atom attacks a methane molecule to form ______.

<p>hydrogen chloride</p> Signup and view all the answers

The mechanism described is known as a free-radical ______.

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

A product from one step of the reaction being a reactant for another step defines a ______ reaction.

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

When most of the reactants have been used up during the reactions, methane radicals and chlorine radicals combine to form ______.

<p>Cl2</p> Signup and view all the answers

In the first step of initiation, a chlorine molecule is broken down into two chlorine atoms in the presence of ______.

<p>ultraviolet light</p> Signup and view all the answers

If excess chlorine is used in the halogenation of alkanes, further substitutions can lead to the formation of ______.

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

No red precipitate is observed. Ketones are not oxidised by ______.

<p>Fehling's solution</p> Signup and view all the answers

Using a graduated disposable pipette, place in a clean test-tube 3 cm^3^ of silver nitrate solution and 1 cm^3^ of ______ solution.

<p>sodium hydroxide</p> Signup and view all the answers

Add aqueous ammonia solution drop by drop, with shaking, until the precipitate formed in stage 1 is just ______.

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

Rinse out the test-tube with dilute ______ acid and then water.

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

Fizzing is observed in the test tube, a mild pop is heard when testing with ______.

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

The lighted taper is extinguished and limewater turns a milky white colour when testing with ______.

<p>sodium carbonate</p> Signup and view all the answers

Ethene and chlorine react to form ______.

<p>1,2-dichloroethane</p> Signup and view all the answers

The first stage of Mass Spectrometry is ______, where the sample material is vaporised into a gas.

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

Particles that are too ______ are deflected too much and hit the side of the spectrometer.

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

Only particles that have a certain ______ are deflected by just the right amount and make it through the spectrometer.

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

The height of each peak in the mass spectrum represents the relative ______ of particles of that mass.

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

Chromatography is a separation technique in which a mobile phase carrying a mixture moves in contact with a selectively ______ stationary phase.

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

In paper chromatography, the stationary phase is ______ paper.

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

In column chromatography, the stationary phase is ______ gel in a glass tube.

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

Passing a solvent through a column is known as ______.

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

The Principle of Gas Chromatography is that a mixture of components is carried by a gaseous mobile phase is separated based on their different ______ with a solid stationary phase.

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

Gas Chromatography uses an inert ______ gas as the mobile phase.

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

The stationary phase in Gas Chromatography is a coiled column filled with coated ______ gel.

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

High Performance Liquid Chromatography (HPLC) utilizes a suitable liquid solvent under high ______.

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

Infra-red spectroscopy helps identify organic compounds by analyzing their absorption of ______ radiation.

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

Ultraviolet spectroscopy results in a fingerprint for each compound and can also measure its ______.

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

In chromatography, a pencil line is made to mark the starting point for ______ placement.

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

Stationary phase for High Performance Liquid Chromatography is also a coated ______ gel.

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

The first step in paper chromatography involves adding ______ to the bottom of the tank.

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

To confirm that a colourless liquid sample was ethanoic acid, a student could add ______ potassium permanganate.

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

A sample of ethene gas can be shown to be unsaturated by adding a ______ solution, which changes from brown to colourless.

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

In paper chromatography, a mixture is applied using a dropper spot on paper slightly above the ______ in the beaker.

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

For recrystallizing impure benzoic acid, the suitable solvent is ______.

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

One flaw in the steam distillation apparatus assembly was that the end of the safety tube was ______ water.

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

Flashcards

Substitution Reaction

A chemical reaction where an atom or group of atoms are replaced by another.

Halogenation of Alkanes

Alkanes reacting with halogens (like chlorine) to form haloalkanes, which are alkanes with some hydrogens replaced by halogens.

Mechanism

Step-by-step, detailed explanation of a chemical reaction.

Free-radical substitution

A type of substitution reaction that involves free radicals as intermediates.

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Chain reaction

A reaction that keeps going because the products from one step make reactants for another.

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Monohalogenation

When one hydrogen atom from the original molecule is replaced by one halogen atom.

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UV light in substitution reactions

Ultraviolet light is required to start free radical substitution reactions, breaking existing bonds.

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Free Radical

An atom or group of atoms with an unpaired electron.

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Chain Reaction (Chloromethane)

A reaction where one step creates intermediates that cause further reactions, leading to many product molecules.

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Free Radicals and Reaction Rate

Reactions involving free radicals (unpaired electrons) are sped up by adding free radicals.

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Esterification Reaction

Combines a carboxylic acid and alcohol, using H2SO4 as a catalyst, to produce an ester.

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Addition Reaction

A reaction where two or more molecules combine to form a single molecule, usually across a double or triple bond.

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Hydrogenation of Oils

Converting unsaturated vegetable oils into saturated fats by adding hydrogen to double bonds.

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Polarization (Br2 and Ethane)

Distortion of electron distribution in a molecule (like Br2) due to proximity to another molecule, making it more reactive.

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Heterolytic Fission

Breaking a bond to form positive and negative ions.

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Carbonium Ion Formation

A positively charged carbon atom formed when a molecule like Br2 approaches and breaks a double bond

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Ketones and Fehling's solution

Ketones do not react with Fehling's solution, showing no oxidation.

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Magnesium and oxidation

Magnesium reacts with an acid or water producing bubbles (fizzing) and a sound.

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Sodium carbonate and litmus test

Sodium carbonate turns a litmus test paper towards a blue colour, showing its basic property and extinguishing a lighted taper.

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Mass spectrometry principle

Mass spectrometry separates charged particles based on their mass differences when in a magnetic field.

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Mass spectrometry vaporization

The initial stage in mass spectrometry where the sample is converted to a gas.

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Mass spectrometry ionization

High-energy electrons convert neutral sample particles into positively charged ions.

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Mass spectrometry acceleration

Positive ions are accelerated by an electric field, increasing their speed to a high rate.

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Mass spectrometry separation

A magnetic field separates these charged particles based on their unique masses.

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Mass Spectrometry

A technique used to identify and quantify different molecules in a sample by separating them based on their mass-to-charge ratio.

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Mass Spectrum

A graph that displays the abundance of ions of different masses, showing peaks corresponding to each ion's mass-to-charge ratio.

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Peak Height in Mass Spectrum

Represents the relative abundance of particles with a specific mass-to-charge ratio.

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Chromatography

A separation technique that separates components of a mixture based on their different affinities for a stationary phase and a mobile phase.

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Stationary Phase (Chromatography)

The fixed material in a chromatography system, which interacts selectively with the components of the mixture being separated.

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Mobile Phase (Chromatography)

The fluid or gas that carries the mixture through the stationary phase in chromatography.

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Paper Chromatography

A type of chromatography where the stationary phase is chromatography paper and the mobile phase is a liquid solvent.

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Elution

The process of eluting a substance from a stationary phase in column chromatography by passing a mobile phase (eluent) through the column.

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Ethanoic acid vs ethanol test

A simple chemical test to differentiate ethanoic acid from ethanol involves adding acidified potassium permanganate. If there is no color change, the liquid is ethanoic acid. If there is a color change, the liquid is ethanol.

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Unsaturated hydrocarbon test

To prove a gas sample is unsaturated, you can add bromine solution. If the bromine solution changes color from brown to colorless, the gas is unsaturated. This is due to the bromine reacting with the double bond present in the unsaturated hydrocarbon.

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Melting point and purity

A pure compound has a sharp melting point, while an impure compound has a wider melting range. This is because impurities disrupt the crystal lattice, causing the compound to melt over a broader temperature range.

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Recrystallization solvent

For recrystallization, a solvent that dissolves the compound well when hot, but poorly when cold is ideal. This allows the compound to crystallize upon cooling, leaving impurities behind in the solution.

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Gas Chromatography (GC)

A technique used to separate different components of a mixture based on their different boiling points. It involves a mobile phase (inert carrier gas) and a stationary phase (coated silica gel in a coiled column).

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Mass Spectrometry (MS)

A technique used to identify and quantify different components in a mixture by measuring their mass-to-charge ratio. Often used in conjunction with GC to analyze separated components.

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Infrared Spectroscopy (IR)

A technique used to identify organic compounds by analyzing their absorption of infrared radiation at different frequencies. Different bonds within a molecule absorb specific IR frequencies, creating a unique 'fingerprint' for each compound.

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Ultraviolet Spectroscopy (UV)

A technique used to identify and quantify organic compounds by analyzing their absorption of ultraviolet light at different wavelengths. Like IR, it creates a unique 'fingerprint' for each compound. It can also measure the concentration of the compound, making it quantitative.

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Stationary Phase

The material that remains fixed in a chromatography system, like the silica gel in GC or paper in paper chromatography, and interacts with the components of the mixture.

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Mobile Phase

The material that moves through a chromatography system, like the gas in GC or the liquid in HPLC, carrying the components of the mixture.

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Study Notes

Substitution Reactions

  • A substitution reaction is a chemical reaction where an atom or group of atoms in a molecule is replaced by another atom or group.
  • Alkanes undergo substitutions in their reactions with halogens in the presence of ultraviolet light.
  • Example: CH4 + Cl2 → CH3Cl + HCl (methane + chlorine → chloromethane + hydrogen chloride)
  • The mechanism of a reaction is a detailed step-by-step description of how the overall reaction occurs.
  • Halogenation of alkanes is a type of substitution reaction.
  • Further substitution can result in dichloromethane (CH2Cl2), trichloromethane (CHCl3), and tetrachloromethane (CCl4).

Mechanism of Monochlorination of Methane

  • The mechanism is known as free-radical substitution.
  • Initiation: A chlorine molecule breaks down into two chlorine atoms in the presence of ultraviolet light.
  • Propagation: A chlorine atom attacks a methane molecule to form hydrogen chloride and a methyl free radical.
  • Propagation: A methyl free radical attacks a chlorine molecule to form chloromethane and a chlorine atom.
  • Termination: When most reactants are used, chlorine and methyl radicals left combine to form Cl2, chloromethane, and ethane.

Evidence for Substitution Mechanisms

  • Reaction takes place when exposed to UV light.
  • For every photon of light absorbed, thousands of chloromethane molecules are formed.
  • Ethane is a product of the reaction.
  • Free radicals speed up the reaction.
  • Inhibitors such as oxygen slow down the reaction.

Addition Reactions

  • An addition reaction is one in which two or more molecules react together to form a single molecule.
  • Always occurs on a double or triple bond.
  • Geometry changes from planar to tetrahedral.
  • Used in the hydrogenation of vegetable oils and formation of plastics.
  • Polarisation: The C=C double bond in ethene has a high concentration of electrons. As Br2 approaches ethene, the electrons repel, polarising the Br2.
  • Heterolytic Fission: The Br2 molecule splits into Br⁺ and Br⁻ ions. Carbonium ion formation: The Br⁺ attacks the electron-rich C=C double bond forming a carbonium ion. Ionic addition: The carbonium ion is then attacked by a Br⁻ ion, forming 1,2-dibromoethane.

Polymerisation Reactions

  • Polymers are long-chain molecules formed by joining many small molecules (monomers) together.
  • Polymers are repeating structures of linked monomers e.g. (Poly)chloroethane, PVC.
  • Definition: The repeating unit of a polymer is the part of the polymer whose repetition produces the complete polymer chain, excluding the end groups. Polyvinyl chloride is synthesised from ethene.

Elimination Reactions

  • An elimination reaction is one where a small molecule is removed from a larger molecule to leave a double bond in the larger molecule.

Redox Reactions

  • When a primary alcohol reacts with an oxidizing agent, the primary alcohol converts to an aldehyde by removing two hydrogen atoms. Example: Primary alcohol → Aldehyde → Carboxylic acid
  • If a secondary alcohol reacts with acidified sodium dichromate, a ketone is formed. Example: Secondary alcohol → Ketone

Mandatory Experiment: To prepare a sample of Soap

  • Detailed procedures are given for the preparation of soap, including the use of lard, potassium hydroxide, and ethanol in a reflux apparatus.

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