Organic Chemistry Halogen Reactions
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Questions and Answers

What is the order of reactivity for halogens in halogenation reactions of alkanes?

  • F2 > Cl2 > Br2 > I2 (correct)
  • Br2 > F2 > I2 > Cl2
  • Cl2 > F2 > Br2 > I2
  • I2 > Br2 > Cl2 > F2
  • Which halogen requires light to react during substitution reactions?

  • Iodine
  • Chlorine (correct)
  • Bromine (correct)
  • Fluorine
  • What product is formed from the reaction of isobutane under chemical oxidation?

  • Butyric acid
  • Hexane
  • Propane
  • Tertiary butyl alcohol (correct)
  • Which halogen does not react at room temperature with alkanes?

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

    What process is described as thermal decomposition or cracking of alkanes?

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

    What is produced when acetic acid is treated with sodium hydroxide and heated?

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

    Which of the following compounds acts as a bridge in the conversion from ethyl chloride to ethyl alcohol involving zinc dust?

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

    What is the resulting compound when sodium iodide is used on a vicinal dihalide?

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

    Which reagent is necessary for converting acetic acid to methane through a series of reactions?

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

    What is formed when ethane is exposed to UV light in the presence of Cl2?

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

    What does Frankland's reaction produce?

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

    Which of the following represents the correct end products of the reaction involving acetone?

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

    What condition is required for the Corey-house synthesis?

    <p>200 o C (D)</p> Signup and view all the answers

    In the Frankland's reaction, what is the role of zinc?

    <p>A reducing agent (C)</p> Signup and view all the answers

    When is the Corey-house synthesis particularly suitable?

    <p>For odd number of alkanes (B)</p> Signup and view all the answers

    What is the starting reactant in the Corey-house synthesis process?

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

    What type of reaction does the combination of CH3-CH2-Cl and lithium lead to?

    <p>Formation of a new alkane (B)</p> Signup and view all the answers

    What byproducts are formed from the reaction involving acetyl chloride?

    <p>Iodine and hydrogen chloride (B)</p> Signup and view all the answers

    What temperature range is used in vapour phase cracking?

    <p>600 – 800°C (A)</p> Signup and view all the answers

    Which compound's presence increases the octane number of gasoline?

    <p>Branched chain hydrocarbons (A)</p> Signup and view all the answers

    What is the effect of increasing the length of the straight chain hydrocarbons on octane number?

    <p>Decreases octane number (A)</p> Signup and view all the answers

    Which method produces a slightly higher yield than the Bergius process?

    <p>Fischer-Tropsch process (B)</p> Signup and view all the answers

    What is added to fuels to reduce knocking properties?

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

    What effect do cyclic alkanes have on octane number?

    <p>They can have a high octane number (C)</p> Signup and view all the answers

    Which of the following processes was invented by Bergius?

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

    Which of these has exceptionally high octane numbers?

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

    What is the primary product of the hydroformylation process described?

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

    Which reagent is necessary to follow the anti Markownikoff's rule in the given reaction?

    <p>C6H5CO3H (C)</p> Signup and view all the answers

    What additional compound is produced when CO and H2O are used in the reaction?

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

    Which of the following best describes the structure of the intermediate formed during the hydroformylation?

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

    In the reaction described, what role does H2 play?

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

    What type of reaction is indicated by the term 'combustion' in the given context?

    <p>Oxidation-reduction (B)</p> Signup and view all the answers

    Which compound acts as a source of carbon monoxide in the hydroformylation reaction?

    <p>CoH(CO)4 (D)</p> Signup and view all the answers

    Which statement best describes the overall reaction involving R-CH=CH-R?

    <p>It results in the formation of a compound with CO and H2. (D)</p> Signup and view all the answers

    What is formed when hydrocarbons undergo combustion in the presence of oxygen?

    <p>Carbon dioxide and water (A)</p> Signup and view all the answers

    What is the role of ozonolysis in organic chemistry?

    <p>To locate the position of double bonds in alkenes (C)</p> Signup and view all the answers

    Which reaction involves the addition of water in an ozonolysis process?

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

    What type of flame is produced during the combustion of hydrocarbons?

    <p>Luminous flame (A)</p> Signup and view all the answers

    What is one of the products formed during the ozonolysis of an alkene?

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

    Which of the following compounds forms an explosive mixture with air during combustion?

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

    What is the chemical fate of alkenes during ozonolysis?

    <p>They are converted to ozonides and then to other products (D)</p> Signup and view all the answers

    When alkenes undergo ozonolysis, which reagent is typically involved in the process?

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

    What class of compounds does ozonolysis help to identify the structure of?

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

    What is the product of the ozonolysis of an alkene followed by a reduction step involving hydrogen?

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

    Flashcards

    Vapour phase cracking

    A process that breaks down larger hydrocarbon molecules into smaller, more volatile ones, typically used to produce gasoline from kerosene or gas oil.

    Octane number

    A measure of a gasoline's resistance to knocking (premature detonation) in an engine. Higher octane numbers mean better performance and less knocking.

    Straight chain hydrocarbons

    A type of hydrocarbon with a straight chain structure. They tend to have lower octane numbers.

    Branched chain hydrocarbons

    Hydrocarbons with branched chains, which generally have higher octane numbers than straight chain hydrocarbons.

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    Antiknock compounds

    Chemicals added to gasoline to improve its anti-knock properties and increase its octane number.

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    TEL (Tetraethyl lead)

    A specific antiknock compound that was widely used but has been phased out due to environmental concerns.

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    Bergius process

    A process that converts coal into a mixture of hydrocarbons, including liquid fuels like gasoline.

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    Fischer-Tropsch process

    A process that converts synthesis gas (CO and H2) into a mixture of hydrocarbons, including liquid fuels like gasoline.

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    Halogenation of Alkanes

    A type of reaction where an alkane reacts with a halogen molecule, replacing a hydrogen atom with a halogen atom.

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    Reactivity of Halogens

    The reactivity of halogens in halogenation reactions decreases as you move down the group in the periodic table. Fluorine is the most reactive, followed by chlorine, bromine, and then iodine.

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    Reaction Conditions for Halogenation

    Fluorine reacts with alkanes even in the dark. Chlorine and bromine require light to initiate the reaction, while iodine is not reactive at room temperature and needs high temperatures for iodination.

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    Thermal Decomposition or Cracking

    A process where an alkane is broken down into smaller hydrocarbons by heating it at high temperatures in the absence of oxygen.

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    Chemical Oxidation of Alkanes

    A process where an alkane is converted to a carboxylic acid by reacting it with oxygen at high temperatures.

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    Reaction of Ethanal with HI

    A reaction where an aldehyde (Ethanal) reacts with hydrogen iodide (HI) in the presence of red phosphorus to form an alkane (Propane) with an even number of carbon atoms. This reaction results in the formation of water and iodine as byproducts.

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    Frankland's Reaction

    A chemical reaction where two alkyl halides (RX) react with zinc to form an alkane with two alkyl groups (R-R) and zinc halide (ZnX2).

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    Reaction of Acetyl Chloride with HI

    A reaction where an acyl chloride (ethanoyl chloride) reacts with hydrogen iodide (HI) in the presence of red phosphorus to form an alkane (ethane) with two carbon atoms. This reaction results in the formation of water, hydrogen chloride (HCl), and iodine as byproducts.

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    Corey-House Synthesis

    A series of chemical reactions used to synthesize alkanes with an odd number of carbon atoms. It involves reacting an alkyl halide with lithium to form a lithium dialkyl cuprate (R2LiCu), which then reacts with another alkyl halide to form an alkane.

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    Lithium Dialkyl Cuprate Formation

    A specific type of reaction used in the Corey-House Synthesis. It involves reacting an alkyl halide with lithium to form a lithium dialkyl cuprate.

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    Reaction of Amide with HI

    The reaction of an amide (CH3-C(=O)-NH2) with hydrogen iodide (HI) in the presence of red phosphorus to form an alkane (Ethane) with two carbon atoms. This reaction results in the formation of water, ammonia (NH3), and iodine as byproducts.

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    Red Phosphorus's Role

    The use of red phosphorus in various reactions with HI, like those mentioned above, to create conditions suitable for the formation of alkanes.

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    Alkane Synthesis

    The main outcome of these reactions: producing alkanes with either an even or an odd number of carbon atoms depending on the specific reagents and method used.

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    Oxidation of an alcohol to an aldehyde

    A chemical reaction where an alcohol is oxidized to an aldehyde, using an oxidizing agent like potassium dichromate (K2Cr2O7) in acidic conditions. The alcohol loses two hydrogen atoms, forming a carbonyl group.

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    Oxidation of an aldehyde to a carboxylic acid

    A chemical process where an aldehyde is further oxidized to a carboxylic acid. This reaction typically involves using oxidizing agents like potassium permanganate (KMnO4) or chromic acid (H2CrO4) in acidic conditions.

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    Halogenation of an alkane

    A reaction where an alkane reacts with chlorine in the presence of UV light to form an alkyl halide. The reaction involves the substitution of a hydrogen atom in the alkane with a chlorine atom.

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    Reduction of an aldehyde to an alcohol

    The reduction of an aldehyde to an alcohol using zinc dust and a strong acid (HX). In this reaction, hydrogen atoms are added to the carbonyl group of the aldehyde, converting it into an alcohol.

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    Conversion of carboxylic acid to a salt

    A reaction where a carboxylic acid is converted into a salt by reacting it with a base like sodium hydroxide (NaOH). This reaction involves the replacement of the acidic hydrogen atom in the carboxylic acid with a sodium atom.

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    Anti-Markovnikov's rule

    A reaction where an electrophile (like H+ from water) adds to the less substituted carbon atom of a double bond, against what would be expected based on Markovnikov's rule.

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    Kharasch Effect

    A specific instance of the anti-Markovnikov's rule where a hydrogen atom adds to the less substituted carbon atom of a double bond, triggered by the presence of peroxy compounds like benzoyl peroxide or peracetic acid.

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    Hydroformylation reaction

    A chemical reaction that adds hydrogen and carbon monoxide to an alkene, forming an aldehyde or ketone.

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    Cobalt tetracarbonyl hydride (CoH(CO)4)

    A catalytic compound used in the hydroformylation reaction, specifically cobalt tetracarbonyl hydride.

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    Oxirane

    A three-membered cyclic ether (containing an oxygen atom) formed by the addition of a hydroxyl group (OH) and a hydrogen atom across the double bond of an alkene.

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    Hydroformylation with water

    A reaction where the hydroformylation reaction is carried out in the presence of water, resulting in the formation of an acid.

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    Combustion reaction

    The process of burning a compound with oxygen, typically resulting in the release of heat and light.

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    Organic reactions and the impact of specific catalysts and reagents

    Anti-Markovnikov's rule, Kharasch Effect, and the hydroformylation reaction all illustrate how reactants can behave in an unexpected way depending on the reaction conditions and presence of specific catalysts.

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    Ozonolysis

    A chemical reaction that breaks down carbon-carbon double bonds (C=C) in alkenes using ozone (O3), followed by a reductive workup.

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    Addition of Formaldehyde

    The process of adding formaldehyde (HCHO) to an alkene, which results in the formation of a cyclic acetal.

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    Alkene

    A type of organic compound with a carbon-carbon double bond (C=C).

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    Ozonolysis: Locating Double Bonds

    The specific position of the double bond in an alkene molecule can be determined using ozonolysis, which breaks the double bond and produces identifiable fragments.

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    Ozonide Formation

    A reaction where an alkene reacts with a molecule of ozone (O3) to form an unstable intermediate called an ozonide.

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    Reductive Workup

    The process of treating an ozonide with a reducing agent like zinc and water to break it down and generate carbonyl compounds.

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    Cyclic Acetal

    A cyclic compound formed by the reaction of an alkene with formaldehyde, where the formaldehyde molecule is attached to the carbon atoms of the double bond.

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    1,2-Diol

    A compound containing a carbon-carbon double bond (C=C) that is specifically located between the first and second carbon atoms of a molecule.

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    Hydrogenation

    A chemical reaction that typically involves the addition of hydrogen (H2) to a double bond, leading to the formation of a saturated compound.

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    Hydration of Alkenes

    A common laboratory procedure that involves heating a mixture of an alkene and a strong acid, leading to the formation of an alcohol.

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    Study Notes

    Hydrocarbons

    • Organic compounds composed of only carbon and hydrogen
    • Two types: Aliphatic and Aromatic
    • Organic compounds composed of only carbon and hydrogen are called hydrocarbons.

    Aliphatic Hydrocarbons

    • Alkanes, Alkenes, and Alkynes
    • Sources: Mineral oil (crude oil), petroleum
      • Petroleum is a dark, oily liquid found underground, often floating on saltwater.
    • Composition:
      • Alkanes: 30-70%; up to 40 carbon atoms, mostly straight chains and some branched chain isomers.
      • Cycloalkanes: 16-64%; cyclohexane, methylcyclopentane, etc.
      • Aromatic hydrocarbons (Arenes), 8-15%: Benzene, Toluene, Xylene, Naphthalene, etc.
      • Sulphur, nitrogen, and oxygen compounds: Sulphur compounds (mercaptans and sulphides), nitrogen compounds (pyridines, quinolines, and pyrroles), oxygen compounds (alcohols, phenols, and resins).
    • Natural Gas: Methane (80%), Ethane (13%), Propane (3%), Butane (1%), low-boiling pentanes and hexanes (0.5%), Nitrogen (1.3%)
      • Used as cooking gas (LPG)
    • Compressed Natural Gas (CNG): Highly compressed natural gas
      • Main component is methane.
    • Theories of Origin: Mendeleev's carbide theory, Engler's organic theory, Modern theory
    • Mining: Petroleum is mined at depths ranging from 500 to 15,000 feet by artificial drilling.
    • Refining: Separation of useful fractions by fractional distillation.
      • Fractions and Uses: Varying boiling points yield different fractions with specific uses (e.g., fuels, lubricants, etc.).
    • Purification: Various treatments like using sulphuric acid to remove aromatic compounds, doctor sweetening process (remove sulphur compounds), and using adsorbents (like alumina, silica or clay).
    • Artificial Petrol/Gasoline Manufacture: Methods like cracking and synthesis are used in artificial petrol/gasoline manufacture.

    Aromatic Hydrocarbons (Arenes)

    • Benzene, Toluene, Xylenes, etc.

    General Methods of Preparation

    • Alkanes:
      • Reaction of alkyl halides with sodium in an aprotic solvent; Wurtz reaction
      • From carboxylic acids: Decarboxylation reaction (Duma reaction)
      • From Grignard reagents
    • Alkenes:
      • From alkyl halides: Dehydrohalogenation reactions (e.g., using alcoholic KOH)
      • From alcohols: Dehydration reactions (e.g., using concentrated H2SO4)
      • From esters: pyrolysis (heating) of esters
    • Alkynes
      • From dihalides
      • From hydrocarbons: By Catalytic Hydrogenation of alkenes and alkynes.
      • From metal acetylide

    Properties and Uses of hydrocarbons

    • Physical properties: State (gas, liquid, solid), boiling point, melting point, density, solubility
    • Chemical properties: Combustion (reaction with oxygen), Substitution, Oxidation, Addition
      • Substitution reactions: Halogenation, Nitration, Sulphonation, Friedel-Crafts alkylation and acylation
      • Addition reactions: Reaction with hydrogen, halogen, hydrogen halides, water and other reagents.
    • Other properties:
      • Isomerisation: Changing a straight-chain alkane to a branched-chain alkane.
      • Aromatisation: Converting a saturated cyclic hydrocarbon molecule into an aromatic hydrocarbon.
    • Specific Uses: Fuel, solvents, feedstock for various industrial processes.
    • Different types of Hydrocarbons have different properties and uses. Their characteristics can be distinguished by different chemical tests.

    Important Numerical Values (For Alkanes, Alkenes, and Alkynes)

    • Bond lengths, bond energies: Vary depending on the type of hydrocarbon

    Degree of Unsaturation

    • Calculations for hydrocarbons to determine if there are multiple bonds or rings

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    Description

    Test your knowledge on halogenation reactions of alkanes and various organic reactions involving halogens. This quiz covers the reactivity order of halogens, reaction conditions, and products formed in these processes. Ideal for students studying organic chemistry.

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