Substitution Reactions: Halogenation of Alkanes

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Questions and Answers

What is the expected observation when ketones are tested with Fehling's solution?

  • A red precipitate forms
  • No change is observed (correct)
  • The solution turns yellow
  • Bubbles are produced

What is the first step in the Tollen's reagent procedure?

  • Heating the solution in a water bath
  • Adding ethanal to the test tube
  • Mixing silver nitrate with sodium hydroxide (correct)
  • Dissolving the precipitate with concentrated sulfuric acid

What gas is produced when magnesium is tested in a solution, as observed?

  • Hydrogen is produced (correct)
  • Oxygen is released
  • Carbon dioxide is generated
  • Nitrogen is emitted

When anhydrous sodium carbonate is added to a test tube, which of the following observations is expected?

<p>The lighted taper is extinguished (A)</p> Signup and view all the answers

Which is NOT a step in the mass spectrometry process?

<p>Formation of more complex molecules (D)</p> Signup and view all the answers

What occurs during the ionisation stage of mass spectrometry?

<p>Electrons are knocked off the sample particles (C)</p> Signup and view all the answers

What is formed as a result of the polymerisation reaction of chloroethene?

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

Which breakdown product is associated with the thermal cracking of 1,2-dichloroethane?

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

What must occur for ethane to be formed in a chain reaction involving chloromethane?

<p>Two methyl free radicals must combine. (D)</p> Signup and view all the answers

Which substance acts as a catalyst in the esterification process mentioned?

<p>Sulfuric acid (D)</p> Signup and view all the answers

In an addition reaction, what is a key characteristic of the bonds involved?

<p>They occur on double or triple bonds. (B)</p> Signup and view all the answers

What is the primary outcome when the C=C double bond in ethene is polarized by Br2?

<p>A carbonium ion is formed. (A)</p> Signup and view all the answers

What happens to the geometry of the molecules during an addition reaction on a double or triple bond?

<p>It changes from planar to tetrahedral. (C)</p> Signup and view all the answers

Which of the following statements about free radicals in the reaction is true?

<p>Only reactions using free radicals will speed up with the addition of more free radicals. (C)</p> Signup and view all the answers

What is the role of the brine in the soap preparation process?

<p>It allows the soap to precipitate out of solution. (C)</p> Signup and view all the answers

What is the primary function of anti-bumping granules in the soap preparation process?

<p>To prevent bumping and ensure smooth boiling. (B)</p> Signup and view all the answers

What determines whether particles pass through the spectrometer to the detector?

<p>The particles' mass (B)</p> Signup and view all the answers

What does the height of a peak in a mass spectrum indicate?

<p>The relative abundance of particles of that mass (A)</p> Signup and view all the answers

Which factor influences the separation in paper chromatography?

<p>Solubility of materials in the mobile phase (B)</p> Signup and view all the answers

In gas chromatography, what does the gaseous mobile phase carry?

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

What is the stationary phase in column chromatography?

<p>Silica gel (D)</p> Signup and view all the answers

Which application is NOT typically associated with mass spectrometry?

<p>Gel electrophoresis (D)</p> Signup and view all the answers

What happens during the elution process in column chromatography?

<p>The solvent is passed through the column (B)</p> Signup and view all the answers

In paper chromatography, where should the spot of the sample mixture be placed?

<p>1 cm above the water line (C)</p> Signup and view all the answers

What type of reaction produces ethene from ethanol?

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

Which of the following statements is true regarding polymerization?

<p>Polymers are made up of repeating units called monomers. (D)</p> Signup and view all the answers

When a primary alcohol is oxidized, it is converted to which compound?

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

What is formed when a secondary alcohol reacts with acidified sodium dichromate?

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

What is the primary product formed when ethene undergoes the addition of bromine in the presence of chlorine ions?

<p>1,2-dibromethane (D)</p> Signup and view all the answers

Which reagent is used in the mandatory experiment to oxidize ethanal?

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

What is the purpose of adding dilute sulfuric acid in the experiment with ethanal and potassium manganate(VII)?

<p>To provide acidity for oxidation (A)</p> Signup and view all the answers

In the oxidation experiment using Fehling's solution, what is the initial color of the solution?

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

What is the role of the mobile phase in gas chromatography?

<p>To carry the sample through the column (B)</p> Signup and view all the answers

How does high-performance liquid chromatography (HPLC) achieve effective separation of components?

<p>By employing a high-pressure pump to force the liquid through the packed column (C)</p> Signup and view all the answers

What type of information can ultraviolet (UV) spectroscopy provide that infrared (IR) spectroscopy cannot?

<p>It can analyze the concentration of a compound (D)</p> Signup and view all the answers

In what application is gas chromatography frequently used?

<p>Measuring alcohol levels in urine samples (C)</p> Signup and view all the answers

Which bonded structure would absorb infrared radiation at a different frequency than C=O in IR spectroscopy?

<p>O-H bond (B)</p> Signup and view all the answers

What is one of the main uses of infrared (IR) spectroscopy?

<p>To identify illegal drugs (D)</p> Signup and view all the answers

What does the coiled column in gas chromatography primarily serve as?

<p>The stationary phase for separating components (A)</p> Signup and view all the answers

During the mandatory experiment of separating ink components using paper chromatography, how is the mobile phase initially prepared?

<p>By pouring the solvent into a tank to a depth of 10 mm (A)</p> Signup and view all the answers

What is the primary purpose of refluxing during the preparation of soap?

<p>To allow time for reaction without losing volatile material (B)</p> Signup and view all the answers

What type of reaction occurs in Stage 1 of soap preparation?

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

Which substance is removed during the distillation in Stage 2?

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

What is the function of the brine in Stage 3 of the soap preparation?

<p>To precipitate the soap (B)</p> Signup and view all the answers

Why is it important to wash the soap thoroughly in Stage 4?

<p>To remove sodium hydroxide (D)</p> Signup and view all the answers

What co-product is formed during the soap preparation process?

<p>Propane-1,2,3-triol (C)</p> Signup and view all the answers

How does sodium stearate interact with oils and salts in sweat?

<p>Its non-polar tail dissolves oils while the ionic head attracts salts (A)</p> Signup and view all the answers

What is the maximum possible yield of soap from 4.45 g of glyceryl tristearate?

<p>4.59 g (C)</p> Signup and view all the answers

Flashcards

Chain Reaction (Chemistry)

A reaction where one step produces a species that starts another step, and so on, similar to a chain.

Free Radical

An atom or molecule with an unpaired electron, highly reactive.

Addition Reaction

A reaction where two or more molecules combine to form a bigger one, often across a double or triple bond.

Esterification

Reaction of carboxylic acid and alcohol to form an ester, catalyzed by acid.

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Saponification

The chemical process of making soap from fats or oils and a base (like potassium hydroxide).

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Hydrogenation of Vegetable Oils

Process that adds hydrogen to vegetable oils to make them more saturated and solid.

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Heterolytic Fission

Bond breaking where electrons are split between the forming ions.

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Ionic Addition Reaction (Mechanism)

A reaction type where a polar molecule adds across a double or triple bond, involving the formation of a cation and an anion and later creating a molecule

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1,2-Dibromoethane Formation

The reaction of ethene with bromine water results in the formation of 1,2-dibromoethane. This happens through an electrophilic addition reaction, where the bromine molecule adds across the double bond of ethene.

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Polymerization

The process of joining many small molecules (monomers) together to form a long chain molecule called a polymer. This occurs through repeated addition reactions involving monomers.

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Repeating Unit

The smallest part of a polymer that, when repeated, makes up the entire polymer chain. It's like the basic building block of the polymer.

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Elimination Reaction

A chemical reaction where a small molecule is removed from a larger molecule, resulting in the formation of a double bond in the larger molecule.

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Oxidation of Primary Alcohol

When a primary alcohol reacts with an oxidizing agent, it is converted into an aldehyde. This involves the removal of two hydrogen atoms from the alcohol.

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Oxidation of Secondary Alcohol

When a secondary alcohol reacts with an oxidizing agent, it is converted into a ketone. This also involves the removal of two hydrogen atoms from the alcohol.

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Reduction of Aldehydes and Ketones

Aldehydes and ketones can be reduced back into alcohols by using hydrogen and a nickel catalyst. This is the reverse reaction of oxidation.

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Ethanal Oxidation

Ethanal (an aldehyde) is easily oxidized by strong oxidizing agents like potassium permanganate (KMnO4) or Fehling's solution. This results in the formation of a carboxylic acid.

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Fehling's Test

A chemical test used to identify reducing sugars (like glucose) by reacting them with Fehling's solution. This solution contains copper ions that are reduced to a red precipitate of copper(I) oxide in the presence of reducing sugars.

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Tollen's Test

A chemical test used to identify aldehydes by reacting them with Tollen's reagent. This reagent is a solution of silver ions that are reduced to metallic silver, forming a silver mirror on the test tube walls in the presence of an aldehyde.

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What does a positive magnesium test indicate?

A positive magnesium test, characterized by fizzing, indicates the presence of an acid. The fizzing is due to the reaction of magnesium with the acid, producing hydrogen gas.

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What does a positive sodium carbonate test indicate?

When anhydrous sodium carbonate reacts with an acid, it produces carbon dioxide gas, which extinguishes a flame and turns limewater milky white, indicating the presence of an acid.

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PVC (Polyvinyl Chloride)

A synthetic polymer produced by polymerizing chloroethene (vinyl chloride). It's widely used in various applications like pipes, insulation, and window frames.

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Mass Spectrometry

A technique that measures the mass-to-charge ratio of ions. This allows the identification and quantification of different molecules in a sample.

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Stages of Mass Spectrometry

Mass spectrometry involves five sequential stages: vaporization, ionization, acceleration, separation, and detection. Each stage plays a critical role in analyzing the sample and generating data.

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Mass Spectrum

A graph that displays the relative abundance of ions with different mass-to-charge ratios.

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What does the height of a peak in a mass spectrum represent?

The height of a peak represents the relative abundance of particles with that specific mass-to-charge ratio.

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Paper Chromatography

A separation technique that uses a stationary phase (paper) and a mobile phase (solvent) to separate components based on their solubility.

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Stationary Phase

The immobile phase in chromatography, which interacts with the components of the mixture being separated.

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Mobile Phase

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

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Gas Chromatography

A separation technique that uses a gaseous mobile phase and a solid stationary phase, separating components based on their boiling points and interactions with the stationary phase.

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Elution

The process of passing a solvent (eluent) through a column containing the stationary phase in chromatography.

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Refluxing

A technique used in chemistry to heat a reaction mixture at its boiling point while preventing the loss of volatile reactants or solvents. It involves the continuous condensation and return of vapors to the reaction flask.

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Distillation

A technique used to separate components of a liquid mixture based on their different boiling points. The mixture is heated, and the component with the lowest boiling point vaporizes and is collected separately.

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Brine

A saturated solution of salt (usually sodium chloride) in water. It is used in various chemical processes to precipitate out certain substances like soap from mixtures.

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Why wash soap?

Washing the soap thoroughly with brine is essential to remove any remaining sodium hydroxide (lye), which is a strong base and can be irritating to skin.

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Co-product of saponification

During saponification, the reaction produces soap and glycerol (propane-1,2,3-triol). Glycerol is a viscous liquid often used in cosmetics and pharmaceuticals.

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Maximum Yield

The theoretical maximum amount of product that can be produced from a given amount of reactants. It is based on the stoichiometry of the reaction, assuming complete conversion of the limiting reagent.

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How soap works

Soap molecules have a polar 'head' (carboxylate group) that is attracted to water (hydrophilic) and a non-polar 'tail' (hydrocarbon chain) that is attracted to oils and fats (hydrophobic). This structure allows soap to dissolve both oils and ionic salts, making it effective in cleaning.

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Gas Chromatography (GC)

A separation technique that uses a non-reactive gas (mobile phase) to carry a mixture through a coiled column packed with a coated silica gel (stationary phase). The components of the mixture separate based on their boiling points and interactions with the stationary phase.

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Uses of GC

Gas Chromatography is used to separate and analyze mixtures, with applications such as measuring alcohol levels in urine samples and drug testing in athletes.

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GC-MS

A combination technique where the separated components from GC are then passed through a Mass Spectrometer to identify each component.

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High Performance Liquid Chromatography (HPLC)

A separation technique that uses a liquid solvent (mobile phase) under high pressure to carry a mixture through a tightly packed column filled with coated silica gel (stationary phase).

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Uses of HPLC

HPLC is used for analyzing mixtures with applications such as testing for Growth Hormones in food and measuring the amount of Caffeine in drinks.

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Infrared Spectroscopy (IR)

A technique that uses infrared radiation to identify organic compounds. Different types of bonds absorb different frequencies of IR radiation, creating a unique spectral fingerprint for each compound.

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Uses of IR Spectroscopy

IR spectroscopy is used for identifying compounds, such as plastics, illegal drugs, and analyzing breathalyser results.

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Ultraviolet Spectroscopy (UV)

A technique that measures how a compound absorbs UV light of different wavelengths. This results in a unique spectral fingerprint for the compound and can also measure the concentration of the compound.

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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 substitution reactions with halogens in the presence of ultraviolet light.
  • Example: CH4 + Cl2 → CH3Cl + HCl (methane reacts with chlorine to form chloromethane and hydrogen chloride).

Halogenation of Alkanes

  • Halogenation is a type of substitution reaction.
  • Halogen atoms replace hydrogen atoms in an alkane molecule.
  • Continued halogenation can lead to the formation of di-, tri-, or tetrachloromethanes.

Mechanism of Monochlorination of Methane

  • The mechanism of a reaction is a step-by-step description of how the overall reaction proceeds.
  • The mechanism of monochlorination of methane is a free-radical substitution mechanism.

Initiation

  • A chlorine molecule is broken down into two chlorine atoms in the presence of ultraviolet light.
  • This creates chlorine free radicals.

Propagation

  • A chlorine free radical attacks a methane molecule, forming hydrogen chloride and a methyl free radical.
  • The methyl free radical attacks another chlorine molecule, forming chloromethane and a chlorine free radical.

Termination

  • When most reactants are used up, remaining chlorine and methyl radicals combine to form Cl2, chloromethane, and ethane, ending the chain reaction.

Evidence for the Mechanism

  • Reaction occurs when exposed to UV light.
  • Thousands of chloromethane molecules are formed for every photon of light absorbed.
  • Ethane is a product of the reaction.
  • Free radicals speed up the reaction.

Addition Reactions

  • An addition reaction is a reaction where two or more molecules combine to form a single molecule.
  • Addition reactions always occur at double or triple bonds.
  • The geometry of the molecule changes from planar to tetrahedral bonds.
  • Examples include hydrogenation of vegetable oils and the formation of plastics.

Polarisation

  • The C=C double bond in ethane has a high concentration of negative charge.
  • As Br2 approaches ethane, electrons are repelled, polarising the Br2 molecule.

Heterolytic Fission

  • The Br2 molecule splits into Br⁺ and Br⁻ ions.

Carbonium Ion Formation

  • The Br⁺ ion attacks the electron-rich C=C double bond.
  • This forms a carbonium ion.

Ionic Addition

  • The carbonium ion is attacked by the Br⁻ ion.
  • This results in the formation of 1,2-dibromethane.

Polymerisation Reactions

  • Polymers are long chain molecules made by joining together many small molecules.
  • Polymers are repeating structures consisting of thousands of monomers linked together.
  • Polyvinyl chloride (PVC) is a common plastic.
  • The repeating unit of a polymer is the part whose repetition forms the complete polymer chain, excluding end groups.

Elimination Reactions

  • An elimination reaction is a reaction where a small molecule is removed from a larger molecule, often producing a double bond in the larger molecule.

Redox Reactions

  • When a primary alcohol reacts with an oxidizing agent, the primary alcohol is converted into an aldehyde.
  • Two hydrogen atoms are removed from the primary alcohol.
  • If a secondary alcohol reacts with acidified sodium dichromate, a ketone is formed.
  • Aldehydes and ketones can be reduced back to alcohols using hydrogen and a nickel catalyst.

Mandatory Experiment: To Prepare Soap

  • Detailed procedures are outlined (using 2.5g of lard, 2.5g KOH, and 20cm³ ethanol, in a reflux apparatus using a water bath, then distillation, dissolution in water, and precipitation in brine followed by filtration).
  • Testing the soap is also outlined.

Mandatory Experiment: To Study Reactions of Ethanal

  • Experiments on ethanal using acidified potassium permanganate, Fehling's reagent, and ammoniacal silver titrate are described.
  • Observations and analysis are discussed for each step.

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