Substitution and Addition Reactions

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Questions and Answers

Free radicals speed up the ______.

reaction

Inhibitors such as ______ slow down the reaction.

oxygen

An ester is formed when a carboxylic acid is reacted with an ______.

alcohol

The process of preparing soap is referred to as ______.

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

An addition reaction always occurs on a ______ or triple bond.

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

The C=C double bond in ______ has a high concentration of negative charge.

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

The Br2 molecule splits into Br^+______ and Br^-.

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

The carbonium ion is then attacked by the ______ ion.

<p>Br^-</p> Signup and view all the answers

The formation of 1,2-dibromethane occurs when the reaction is carried out in bromine water with ______ ions added.

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

Polymers are long chain molecules made by joining together many small ______.

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

The repeating unit of a polymer is that part of the polymer whose repetition produces the complete polymer ______.

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

Ethene can be produced from ethanol by means of an ______ reaction.

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

When a primary alcohol reacts with an oxidising agent, it is converted to an ______.

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

Aldehydes and ketones can be reduced back to alcohols in the presence of ______ and a nickel catalyst.

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

To oxidise ethanal with potassium manganate(VII), one needs to add dilute sulfuric ______.

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

In the reaction with Fehling's solution, the initial formation of a blue ______ is observed.

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

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

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

The height of each peak in a 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

Less soluble materials will appear as a spot closer to the ______ of the paper.

<p>bottom</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

The principle of gas chromatography is that a mixture of components is carried by a gaseous mobile phase and separated based on their different interactions with a solid ______ phase.

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

The process of passing a solvent through a column in chromatography is known as ______.

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

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

<p>Fehling</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 ______ solution drop by drop, with shaking, until the precipitate formed is just dissolved.

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

The lighted taper is extinguished and limewater turns a milky white ______ when sodium carbonate is tested.

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

In the synthesis of PVC from ethene, ethene and chlorine react to form ______.

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

In Mass Spectrometry, the sample material is vaporised into a ______.

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

The chloroethene undergoes a ______ reaction to form polychloroethene (PVC).

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

A magnetic field of a particular strength is used to ______ the particles in Mass Spectrometry.

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

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

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

The mobile phase in Gas Chromatography is an inert carrier ______.

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

Gas Chromatography is often paired with Mass ______ for component identification.

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

In High Performance Liquid Chromatography, the stationary phase is a coated ______.

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

Ultraviolet Spectroscopy provides a ______ for each compound by measuring how it absorbs UV light.

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

Infra-red Spectroscopy identifies organic compounds based on how they absorb ______ radiation.

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

In paper chromatography, a solvent is added to the tank to a depth of about ______ mm.

<p>10</p> Signup and view all the answers

The mobile phase in High Performance Liquid Chromatography is a suitable liquid ______ under high pressure.

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

The ______ level in the tank must be below the line on which the indicator samples are spotted.

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

The process of heating the mixture for a prolonged time without losing volatile materials is called ______.

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

During Stage 2, the substance removed by distillation was ______.

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

To precipitate the soap, the function of ______ in Stage 3 was crucial.

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

Washing the soap thoroughly in Stage 4 was necessary to remove ______.

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

The co-product of the reaction, also known as propane-1,2,3-triol, was found in the ______ at the end of the process.

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

Sodium stearate can dissolve both non-polar oils and ionic salts in sweat due to its ______ structure.

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

The reaction type that occurred during the soap preparation is known as ______.

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

Flashcards

Chain Reaction (in Chemistry)

A reaction where one step produces something that starts the next step, repeating the process.

Free Radicals and Reaction Speed

Adding free radicals speeds up reactions involving free radicals.

Esterification

Reaction between a carboxylic acid and an alcohol, using sulfuric acid as a catalyst, to form an ester.

Addition Reaction

Two or more molecules combine to form a single molecule, typically on a double or triple bond.

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Hydrogenation of Vegetable Oils

An addition reaction used to turn vegetable oils into more solid fats.

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Polarization (in Chemistry)

Distortion of electron distribution in a molecule when a different molecule approaches, making one side slightly positive and the other negative.

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Heterolytic Fission

A molecule splitting into positively and negatively charged parts (ions).

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Ionic Addition Reaction

An addition reaction where the attacking species and the target molecule both become ions and react, forming a carbonium ion before an ion to the target.

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Polymer Definition

A polymer is a long molecule made of many small molecules (monomers) joined together.

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Repeating Unit (Polymer)

The part of a polymer that repeats to form the whole chain, excluding the end groups.

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Elimination Reaction

A reaction where a small molecule is removed from a larger molecule, creating a double bond.

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Ethene Production

Ethene can be made from ethanol by removing water (elimination reaction).

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Primary Alcohol Oxidation

When a primary alcohol reacts with an oxidizer, it forms an aldehyde, losing hydrogen atoms.

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Secondary Alcohol Oxidation

A secondary alcohol reacts with acidified sodium dichromate to form a ketone.

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Aldehyde Reduction

Aldehydes can be changed back to alcohols by using hydrogen and a nickel catalyst.

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1,2-dibromomethane formation

In a reaction with bromine water and added chloride ions, sometimes other products are formed including 1-bromo-2-chloroethane and 2-bromoethanol

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Mass Spectrometry

A technique that measures the mass-to-charge ratio of ions.

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Mass Spectrum

A graph that displays the relative abundance of different masses of particles.

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Chromatography

A separation technique using a stationary and mobile phase.

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Paper Chromatography

A chromatography type using paper as a stationary phase and a solvent as a mobile phase.

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Stationary Phase

The stationary material in chromatography.

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Mobile Phase

The moving liquid or gas that carries the mixture in chromatography.

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Elution

The process of passing a solvent (eluent) through a column in chromatography.

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Gas Chromatography

A chromatography technique using a gaseous mobile phase.

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Refluxing

Heating a reaction mixture while continuously condensing and returning vapors back to the reaction vessel.

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Saponification

A chemical reaction that breaks down fats (like glyceryl tristearate) into soap and glycerol, using a strong base like sodium hydroxide.

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Distillation

Separating components of a mixture based on their different boiling points by vaporizing and condensing them.

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Brine

Concentrated saltwater solution used to precipitate soap.

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Co-product of Saponification

Glycerol (propane-1,2,3-triol) is the other main product formed along with soap during saponification.

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Maximum Yield Calculation

Finding the highest possible amount of product that can be made from a given amount of reactants.

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Soap Structure and Function

Sodium stearate (soap) has a long non-polar hydrocarbon chain that dissolves oils and an ionic head (COO^-Na+) that attracts salts and polar molecules in sweat.

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R*f* Value

The ratio of the distance traveled by a substance to the distance traveled by the solvent in a chromatography experiment.

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Gas Chromatography (GC)

A technique used to separate components of a mixture based on their different boiling points. It uses a carrier gas (mobile phase) to move the mixture through a column packed with a stationary phase.

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GC-MS

A combination of Gas Chromatography and Mass Spectrometry. After separating components by GC, each component is passed through a Mass Spectrometer, which identifies each component by its mass-to-charge ratio.

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High Performance Liquid Chromatography (HPLC)

A technique similar to GC, but uses a liquid solvent (mobile phase) under high pressure to move the mixture through a column packed with a stationary phase. It's useful for separating components with similar boiling points or those that decompose at high temperatures.

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HPLC Stationary Phase

A tightly packed material, often coated silica gel, that interacts with the components of the mixture based on their chemical properties. It's similar to GC, but tailored for liquid mobile phases.

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HPLC Mobile Phase

A liquid solvent, like ethanol, under high pressure that pushes the mixture through the column. It's chosen based on the properties of the components to be separated.

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Infrared Spectroscopy (IR)

A technique that measures the absorption of infrared radiation by a compound. Different types of bonds in molecules absorb specific frequencies of IR light, creating a unique fingerprint for each compound.

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Fehling's Test

A test for the presence of aldehydes. It involves reacting the compound with Fehling's solution, a mixture of copper(II) sulfate and sodium hydroxide. If the compound is an aldehyde, it will be oxidized to a carboxylic acid, and a red precipitate of copper(I) oxide will form.

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Tollen's Reagent

A solution of silver nitrate and ammonia used to detect aldehydes. In this reagent, the silver ions are reduced to metallic silver by an aldehyde, creating a silver mirror on the inside of the test tube.

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What does a positive Tollen's test indicate?

A positive Tollen's test indicates the presence of an aldehyde. The aldehyde is oxidized to a carboxylic acid, and the silver ions are reduced to metallic silver, forming a silver mirror.

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Magnesium Test

A reaction involving a magnesium strip placed in a test tube with a solution of the compound. Fizzing and a pop sound indicate the presence of an acid.

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Sodium Carbonate Test

A reaction where sodium carbonate is added to a solution of the compound. If the lighted taper is extinguished and limewater turns milky white, it indicates the presence of carbon dioxide.

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Thermal Cracking

A process where a large molecule is broken down into smaller molecules by heating it. This is a critical step in the production of chloroethene from 1,2-dichloroethane.

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Polymerization

A process where many small molecules (monomers) join together to form a large chain-like molecule (polymer). PVC is formed by polymerizing chloroethene.

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Study Notes

Substitution Reactions

  • Substitution reaction: A chemical reaction where an atom or group of atoms in a molecule is replaced by another atom or group.
  • Halogenation of alkanes: Alkanes react with halogens (e.g., chlorine, bromine) in the presence of ultraviolet light, undergoing substitution.
  • Mechanism of monochlorination of methane: A free-radical substitution mechanism.
    • Initiation: A chlorine molecule breaks down into two chlorine atoms.
    • Propagation: A chlorine atom attacks a methane molecule, chlorine atom reacts with methyl free radical, methyl free radical attacks a chlorine molecule forming chloromethane and chlorine atom.
    • Termination: Chlorine radicals and methyl radicals combine to form Cl2, chloromethane and ethane.
    • Evidence: Reaction occurs when exposed to UV light, thousands of chloromethane molecules are formed, free radicals speed up the reaction, and inhibitors slow the reaction down.

Addition Reactions

  • Addition reaction: Two or more molecules combine to form a single molecule, always on a double or triple bond causing a change in geometry from planar to tetrahedral bonds.
    • Used in hydrogenation of vegetable oils, and to form plastics.
    • Polarisation: The C=C double bond in ethene has a high concentration of negative charge; as Br2 approaches, the electrons repel away polarising Br2.
    • Heterolytic fission: Br2 splits into Br⁺ and Br⁻ ions.
    • Carbonium ion formation: Br+ attacks the electron-rich C=C bond. Forming a carbonium ion.
    • Ionic Addition: The cation is attacked by the bromide ion to form 1,2-dibromoethane.
    • Evidence: Reaction takes place when exposed to UV light; thousands of chloromethane molecules are formed and free radicals speed up the reaction.

Polymerisation Reactions

  • Polymer definition: Long-chain molecules formed by combining many small molecules (monomers).
  • Polymers are repeating structures consisting of thousands of monomers linked together. PVC is a common plastic.
  • Polymer repeating unit: The part of the polymer whose repetition produces the complete polymer chain, excluding the end groups.

Elimination Reactions

  • Elimination reaction: A small molecule is removed from a larger molecule, leaving a double bond in the larger molecule.

Redox Reactions

  • Redox reactions: Reactions involving the transfer of electrons between molecules.
    • Primary alcohols oxidised to aldehydes, losing 2 hydrogen atoms.
    • Secondary alcohols oxidised to ketones, also losing 2 hydrogen atoms.
      • Aldehydes and ketones reduced back to alcohols by hydrogen and a nickel catalyst.
  • Mandatory experiment: Studying the reaction of ethanal with acidified potassium permanganate solution, Fehling's reagent, and ammoniacal silver titrate (oxidation by acidified potassium manganate).

Esterification

  • Esterification: Carboxylic acid reacts with an alcohol in the presence of H2SO4 catalyst, forming an ester. Saponification is the term for the reaction.
  • Mandatory experiment: Preparing a sample of soap involves reaction of lard, potassium hydroxide, and ethanol, followed by distillation to remove ethanol, dissolving the residue in hot water, and precipitating the soap via the addition of brine.

Organic Acids

  • Carboxylic acid group involves inductive effect, making the carbon atom of the carbonyl group slightly positive; Inductive effect means that the carbon atom pulls electrons from the oxygen atom to the -OH group.
  • Stability of carboxylate ion: The negative charge is delocalised between the two oxygens and is not localised to just one oxygen.
  • Mandatory experiment: Testing the effects of ethanoic acid with sodium carbonate, magnesium, and ethanol.

Other reactions and experiments

  • Mandatory experiment to separate components of ink using paper chromatography.
  • Separation from a mixture by paper chromatography (solvent in a beaker that soaks up through the paper separating components based on extent of dissolving).

Mass Spectrometry

  • Principle of Mass Spectrometry: Charged particles moving in a magnetic field are deflected by different amounts due to their masses, separating the particles based on mass.
  • Processes involved in mass spectrometry: Vaporisation, Ionisation, Acceleration, Separation, Detection.
  • Mass spectrum output: Peaks in the mass spectrum, with abundance of particles.

Chromatography (general)

  • Chromatography: Separation technique using a mobile phase that carries mixtures and a stationary phase with selective adsorption of components.
    • Types of chromatography: Paper chromatography, column chromatography, GC, HPLC.
      • Paper chromatography principle: components dissolve different to varying degrees (more soluble = higher it goes) on stationary phase (paper).

Spectroscopy

  • Spectroscopy, measuring how compounds react to different frequencies (energies) of light or radiation, including infrared (IR), ultraviolet (UV).

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