Organic Chemistry Lecture 4

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Questions and Answers

What type of reaction occurs when alkanes combust?

  • Reduction reaction
  • Oxidation reaction (correct)
  • Substitution reaction
  • Decomposition reaction

Which law states that equal volumes of gases at the same conditions contain the same number of molecules?

  • Boyle's Law
  • Charles's Law
  • Gay-Lussac's Law
  • Avogadro's Law (correct)

During the combustion analysis of a hydrocarbon, what products are typically formed?

  • Carbon monoxide and water
  • Methane and oxygen
  • Ethane and carbon
  • Carbon dioxide and water (correct)

What is the primary reason why alkanes are considered relatively inert?

<p>They are non-polar and covalent (B)</p> Signup and view all the answers

In combustion analysis, if 80 mL of the mixture after combustion is carbon dioxide, what information does it provide about the hydrocarbon?

<p>The molecular formula can be deduced using ratios (B)</p> Signup and view all the answers

What is the significance of the residual volume measured after combustion analysis?

<p>It shows the amount of oxygen unused (A)</p> Signup and view all the answers

The reaction of methane with chlorine exemplifies which type of reaction?

<p>Free radical halogenation (C)</p> Signup and view all the answers

What can be determined through combustion analysis of a known hydrocarbon?

<p>Its molecular weight (C)</p> Signup and view all the answers

What is the main characteristic of bromine compared to chlorine or fluorine in terms of selectivity?

<p>Bromine is more selective than chlorine. (C)</p> Signup and view all the answers

In the bromination reaction of alkane, what is a likely product when light is applied?

<p>An alkane with one bromine atom (C)</p> Signup and view all the answers

Which of the following statements about free radicals is true?

<p>Free radicals are thought to contribute to various human diseases. (B)</p> Signup and view all the answers

What reaction typically occurs when alkanes react with chlorine in the presence of light?

<p>Production of chlorinated alkanes with potential low yield (D)</p> Signup and view all the answers

During the termination phase of free radical reactions, what typically happens?

<p>Radicals combine to form stable molecules. (B)</p> Signup and view all the answers

What is a likely outcome of a reaction involving bromine and an alkane when using light as a catalyst?

<p>Yield of brominated compounds may vary greatly (D)</p> Signup and view all the answers

What is the purpose of determining the percent composition of elements in a compound?

<p>To determine the empirical and molecular formula (D)</p> Signup and view all the answers

What type of diseases can be explained by reactions of free radicals with biological substances?

<p>Most age-related diseases (C)</p> Signup and view all the answers

Which of the following products is typically expected from the reaction of alkanes with bromine in the presence of light?

<p>Mono-brominated alkanes (B)</p> Signup and view all the answers

Which formula represents the empirical formula of a compound?

<p>The relative proportions of elements in a molecule (B)</p> Signup and view all the answers

In the context of percent composition, what does the variable 'n' represent?

<p>Number of moles of an element (A)</p> Signup and view all the answers

During free radical halogenation, what is the primary role of the initiation step?

<p>To generate free radicals (D)</p> Signup and view all the answers

Which of the following statements is true regarding the stability of free radicals in halogenation reactions?

<p>Tertiary free radicals are the most stable (D)</p> Signup and view all the answers

What is formed during the dihalogenation of an alkane?

<p>A dichlorinated product and a hydrogen halide (A)</p> Signup and view all the answers

What is the primary risk associated with the use of fluorine in free radical halogenation?

<p>It is highly explosive (C)</p> Signup and view all the answers

In the molecular formula determination, what is the final step after obtaining the mole ratios?

<p>Convert the ratios to whole numbers (D)</p> Signup and view all the answers

What type of substitution reaction results in multiple halogen atoms being added to an alkane?

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

What happens during the termination step of free radical halogenation?

<p>Free radicals combine to form stable products (A)</p> Signup and view all the answers

Flashcards

What are alkanes?

Alkanes are hydrocarbons that contain only single bonds between carbon atoms. They are relatively unreactive due to their non-polar covalent bonds.

Combustion of Alkanes

The burning of alkanes in the presence of oxygen, releasing heat and light, forming carbon dioxide (CO2) and water (H2O).

Gay-Lussac's Law

This law states that the volumes of gases involved in a chemical reaction, at constant temperature and pressure, are in a simple ratio to each other.

Avogadro's Law

This law states that equal volumes of gases at the same temperature and pressure contain the same number of molecules.

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What is Combustion Analysis?

A technique used to determine the empirical formula of a hydrocarbon by reacting a known volume of the hydrocarbon with oxygen and measuring the volumes of the products (CO2 and H2O) and unreacted oxygen.

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What is the general equation for hydrocarbon combustion?

CxHy + (x + y/4)O2 -> xCO2 + (y/2)H2O

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What is the purpose of combustion analysis?

Combustion analysis can: 1) Determine the empirical formula of a hydrocarbon. 2) Determine the molecular weight of an alkane by knowing the volume of the hydrocarbon and the volumes of the products and unreacted oxygen.

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How does the volume of the product gases relate to the original volume of the hydrocarbon and oxygen?

The total volume of the product gases (CO2 and H2O) plus the unreacted oxygen is less than the original volume of the hydrocarbon and oxygen due to the formation of water (H2O), which is a liquid at room temperature.

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Propagation (Free Radical Reaction)

A series of steps in a free radical reaction where the radical intermediates are continuously regenerated.

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Termination (Free Radical Reaction)

The final step in a free radical reaction where two radicals combine to form a stable molecule, ending the chain reaction.

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Free Radical

An atom or molecule with an unpaired electron, making it highly reactive and seeking to pair up with another electron.

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Bromine Selectivity

Bromine is more selective than chlorine or fluorine in free radical reactions, preferentially reacting with the most stable radical intermediate.

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Free Radical Stability

The stability of a free radical is determined by the number of alkyl groups attached to the carbon atom with the unpaired electron. More alkyl groups = more stable.

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Free Radicals in Diseases

Free radicals are implicated in various diseases, especially those related to aging, by damaging biological molecules.

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Free Radical Damage

Free radicals can damage important biomolecules like DNA, proteins, and lipids, contributing to disease development.

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Age-Related Diseases

Many age-related diseases are linked to free radical damage to biological molecules over time.

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Empirical Formula

The simplest whole number ratio of atoms in a compound. It represents the relative proportions of elements, not the actual number of atoms.

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Percent Composition

The percentage by mass of each element in a compound. Found experimentally by determining the mass of each element in a given sample.

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Molecular Formula

The actual number of atoms of each element in a molecule. Shows the exact composition of a molecule.

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Free Radical Halogenation

A reaction involving alkanes and halogens where a halogen atom is substituted for a hydrogen atom on the alkane. It proceeds via a free radical mechanism.

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Initiation

The first step in the free radical halogenation mechanism. It involves the homolytic cleavage of a halogen molecule into two free radicals.

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Propagation

The chain reaction steps in halogenation where a free radical reacts with an alkane molecule, forming a new free radical which then continues the cycle.

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Termination

The final steps in halogenation where two free radicals combine to form a stable product. This stops the chain reaction.

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Primary (1o) Carbon

A carbon that is directly bonded to just one other carbon atom.

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Secondary (2o) Carbon

A carbon atom bonded to two other carbon atoms.

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Tertiary (3o) Carbon

A carbon atom bonded to three other carbon atoms.

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Study Notes

Organic Chemistry Lecture 4

  • Organic chemistry lecture 4 covers reactions of alkanes, combustion analysis of hydrocarbons, free radical halogenation, reactions of higher alkanes, cycloalkanes, and double bond equivalents.

Reactions of Alkanes

  • Alkanes have non-polar, covalent bonds, making them relatively inert.
  • They do not typically react with acids, bases, or reducing agents.
  • Alkanes are used as fuels.
  • Combustion (burning) of alkanes releases heat and light.
  • The general combustion reaction for methane is CHâ‚„ + 2Oâ‚‚ → COâ‚‚ + 2Hâ‚‚O + heat.

Combustion Analysis of Hydrocarbons

  • Gay-Lussac's Law: Volumes of gases in a reaction are numerically related at standard temperature and pressure (STP).
  • Avogadro's Law: Equal volumes of gases at STP contain equal numbers of molecules.
  • Combustion analysis involves reacting a known volume of hydrocarbon with a known volume of oxygen.
  • The volume of products and unreacted oxygen after cooling is measured.
  • This method determines the molecular weight of the alkane.

Free Radical Halogenation

  • The reaction of methane with chlorine is an example of free radical halogenation, a process with three steps.
  • Initiation, propagation and termination
  • The substitution reaction produces different products depending on the carbon’s position (primary, secondary, tertiary).
  • Bromine is more selective than chlorine or fluorine.

Cycloalkanes

  • Cycloalkanes are saturated hydrocarbons with at least one ring of carbon atoms.
  • Their general formula is Câ‚™Hâ‚‚â‚™.
  • They are named by adding the prefix "cyclo" to the corresponding alkane name.
  • Cis-trans isomerism is possible in cycloalkanes.

Double Bond Equivalents (DBE)

  • DBE provides information on the number of double bonds or rings in an organic compound.
  • DBE is related to the degree of saturation/unsaturation of the compound.
  • The formula for calculating DBE is: DBE = 1 + C - (H/2) - (X/2) + N/2

Past Paper Questions

  • Several past paper questions are included for practice, involving calculations and mechanisms. Example: 2-Methylpropane reacts with bromine (July/August 2004).

Determination of Molecular Formulae using Percent Composition

  • Percent composition (by mass) of elements in a sample is obtained experimentally.
  • It is used for determining the empirical and molecular formula of a compound.
  • Empirical formula shows the relative proportions of elements in a molecule. Calculation involves converting percent composition to moles, and then to mole ratios.

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