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Questions and Answers
What type of reaction is the conversion of an alcohol to an alkene?
What type of reaction is the conversion of an alcohol to an alkene?
Tertiary alcohols are easily oxidized using acidified potassium dichromate(VI).
Tertiary alcohols are easily oxidized using acidified potassium dichromate(VI).
False
What color change is observed when an alcohol is oxidized with potassium dichromate(VI)?
What color change is observed when an alcohol is oxidized with potassium dichromate(VI)?
orange to green
Primary alcohols can be oxidized to aldehydes, and further oxidized to ______.
Primary alcohols can be oxidized to aldehydes, and further oxidized to ______.
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Match the following alcohols with their oxidation products:
Match the following alcohols with their oxidation products:
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Which reagent can be used to convert an alcohol to an iodoalkane?
Which reagent can be used to convert an alcohol to an iodoalkane?
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Haloalkanes contain nonpolar bonds due to the similar electronegativity of carbon and halogen atoms.
Haloalkanes contain nonpolar bonds due to the similar electronegativity of carbon and halogen atoms.
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What type of product is formed when a secondary alcohol is oxidized?
What type of product is formed when a secondary alcohol is oxidized?
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What is the primary function of the condenser in a reflux apparatus?
What is the primary function of the condenser in a reflux apparatus?
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In a distillation setup, the liquid with the higher boiling point evaporates first.
In a distillation setup, the liquid with the higher boiling point evaporates first.
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What property difference allows a separating funnel to separate liquids?
What property difference allows a separating funnel to separate liquids?
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The purer a substance, the ______ to the databook boiling point it will be.
The purer a substance, the ______ to the databook boiling point it will be.
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Match each piece of apparatus with its primary use:
Match each piece of apparatus with its primary use:
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What is the purpose of using an inverted capillary tube when determining a substances boiling point?
What is the purpose of using an inverted capillary tube when determining a substances boiling point?
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Redistillation is done to obtain a less pure product.
Redistillation is done to obtain a less pure product.
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When determining boiling point, what observation is made to determine the exact boiling point temperature?
When determining boiling point, what observation is made to determine the exact boiling point temperature?
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The fingerprint region of an IR spectrum is unique to each molecule and can be used to identify it.
The fingerprint region of an IR spectrum is unique to each molecule and can be used to identify it.
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The absorption of infrared radiation by atmospheric gases containing C=O, O–H, and C–H bonds, such as CO₂, H₂O, and CH₄, is linked to ______.
The absorption of infrared radiation by atmospheric gases containing C=O, O–H, and C–H bonds, such as CO₂, H₂O, and CH₄, is linked to ______.
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Which of the following is NOT a use of Infrared Spectroscopy?
Which of the following is NOT a use of Infrared Spectroscopy?
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Match the following steps in TOF mass spectrometry with their corresponding descriptions.
Match the following steps in TOF mass spectrometry with their corresponding descriptions.
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What is a nucleophile described as?
What is a nucleophile described as?
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Nucleophilic substitution can occur for tertiary haloalkanes.
Nucleophilic substitution can occur for tertiary haloalkanes.
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What is the purpose of the magnetic field in TOF mass spectrometry?
What is the purpose of the magnetic field in TOF mass spectrometry?
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What does the 'm/z' value in mass spectrometry represent?
What does the 'm/z' value in mass spectrometry represent?
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What type of product is formed when haloalkanes react with aqueous potassium hydroxide?
What type of product is formed when haloalkanes react with aqueous potassium hydroxide?
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The greater the Mr of the halogen in the polar bond, the ______ the bond enthalpy.
The greater the Mr of the halogen in the polar bond, the ______ the bond enthalpy.
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The molecular ion peak in a mass spectrum is the peak furthest to the left, representing the ion with the lowest mass-to-charge ratio.
The molecular ion peak in a mass spectrum is the peak furthest to the left, representing the ion with the lowest mass-to-charge ratio.
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Match the nucleophiles with their products after reaction with haloalkanes:
Match the nucleophiles with their products after reaction with haloalkanes:
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Explain how the relative abundance of each isotope is determined in TOF mass spectrometry.
Explain how the relative abundance of each isotope is determined in TOF mass spectrometry.
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What role do chlorine radicals play in the breakdown of ozone?
What role do chlorine radicals play in the breakdown of ozone?
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CFCs are haloalkanes containing carbon, chlorine, and fluorine atoms, but not oxygen.
CFCs are haloalkanes containing carbon, chlorine, and fluorine atoms, but not oxygen.
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What is the overall equation for the breakdown of ozone by chlorine radicals?
What is the overall equation for the breakdown of ozone by chlorine radicals?
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Which of the following is a common anhydrous salt used for drying compounds?
Which of the following is a common anhydrous salt used for drying compounds?
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Addition reactions are less sustainable than substitution reactions.
Addition reactions are less sustainable than substitution reactions.
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What is the process called that involves converting an organic compound into a product through multiple stages?
What is the process called that involves converting an organic compound into a product through multiple stages?
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Bromine water is used to test for __________.
Bromine water is used to test for __________.
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Match the following tests with the substances they detect:
Match the following tests with the substances they detect:
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When analyzing synthetic routes, why is it preferable to choose reagents with fewer safety concerns?
When analyzing synthetic routes, why is it preferable to choose reagents with fewer safety concerns?
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The identification of functional groups can be performed using various tests.
The identification of functional groups can be performed using various tests.
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What effect does infrared (IR) radiation have on covalent bonds?
What effect does infrared (IR) radiation have on covalent bonds?
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Which functional group is identified by a sharp peak in the range of 1620-1680 cm-1?
Which functional group is identified by a sharp peak in the range of 1620-1680 cm-1?
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A broad, smooth peak in the IR spectrum indicates the presence of a carboxylic acid functional group.
A broad, smooth peak in the IR spectrum indicates the presence of a carboxylic acid functional group.
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What does the IR spectrum primarily measure when analyzing organic compounds?
What does the IR spectrum primarily measure when analyzing organic compounds?
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The characteristic peak range for the C=O carbonyl group is ________ cm-1.
The characteristic peak range for the C=O carbonyl group is ________ cm-1.
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Match the functional groups with their characteristic peak ranges:
Match the functional groups with their characteristic peak ranges:
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Which functional group can be identified by both a C=O bond peak and a broad O–H bond peak?
Which functional group can be identified by both a C=O bond peak and a broad O–H bond peak?
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At approximately what cm⁻¹ will most organic compounds produce a peak due to C–H bonds?
At approximately what cm⁻¹ will most organic compounds produce a peak due to C–H bonds?
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Infrared spectroscopy can distinguish between aldehydes and ketones solely by their C=O absorption peaks.
Infrared spectroscopy can distinguish between aldehydes and ketones solely by their C=O absorption peaks.
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Study Notes
Alcohols
- Alcohols contain an -OH group and follow the general formula CnH2n+1OH.
- They can be classified as primary (1°), secondary (2°), or tertiary (3°) depending on the position of the hydroxyl group.
- Alcohols are polar molecules due to the large electronegativity difference between carbon and oxygen, allowing hydrogen bonding with water.
- This hydrogen bonding makes alcohols water-soluble.
- Alcohols have both hydrogen bonding and van der Waals forces, making them less volatile than alkanes.
- Alcohols combust in air, reacting with oxygen to form carbon dioxide and water, releasing energy.
- (Example: 2CH3OH + 3O2 → 2CO2 + 4H2O)
Reactions of Alcohols
- Combustion: Alcohols react with oxygen to form carbon dioxide and water, releasing energy, making them good fuels.
- Reaction with halogenating agents: Alcohols can react with halogenating agents (like PCl3) to form haloalkanes, replacing the -OH group with a halogen. This reaction can be used as a test for alcohols.
- Elimination Reactions: Alkenes can be produced from alcohols through dehydration, where a molecule of water is removed, typically by heating the alcohol with concentrated phosphoric acid.
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Oxidation of Alcohols:
- Primary alcohols can be oxidised to aldehydes and further to carboxylic acids with acidified potassium dichromate(VI).
- Secondary alcohols are oxidised to ketones with acidified potassium dichromate(VI).
- Tertiary alcohols are not easily oxidised.
Haloalkanes
- Haloalkanes contain polar bonds because halogens are more electronegative than carbon.
- This creates a partial positive charge on the carbon and a partial negative charge on the halogen.
- They are classified as primary, secondary, or tertiary based on the position of the halogen in the carbon chain.
- Reactivity varies between halogens, decreasing down the group from fluorine to iodine. This is due to decreasing bond enthalpy.
Substitution Reactions of Haloalkanes
- Haloalkanes react with aqueous alkali (like NaOH) in a nucleophilic substitution reaction to form alcohols.
- Haloalkanes react with ethanolic potassium hydroxide (KOH) to form alkenes via an elimination reaction.
- Haloalkanes react with aqueous silver nitrate to form precipitates, with the colour of the precipitate indicating the halide ion. The rate of precipitate formation correlates to the stability of the haloalkane. Iodoalkanes are hydrolysed faster than bromoalkanes, which are faster than chloroalkanes.
Nucleophilic Substitution Mechanism
- Nucleophiles, electron-pair donors, attack haloalkanes in a specific mechanism.
- This depends on the type of nucleophile and the structure of the haloalkane (primarily 1° and 2°).
Environmental Concerns
- Organohalogen compounds, like CFCs, can break down the ozone layer in the atmosphere through a catalytic reaction.
- Ultraviolet radiation initiates the breakdown.
Organic Synthesis
- Practical Skills: Heating under reflux (for reactions that need extended heating) and distillation (to separate liquids with different boiling points) are important techniques.
- Synthetic Routes: In the preparation of an organic compound, choosing appropriate synthetic routes based on reagents, byproducts, and reaction conditions to ensure efficiency and safety is important.
- Multi-stage Synthesis: In the preparation of complex organic molecules, steps involving intermediate molecules can improve efficiency.
Analytical Techniques
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Infrared Spectroscopy (IR): IR radiation causes covalent bonds to vibrate, and the absorbed energy is used to identify functional groups by their unique absorption patterns in the IR spectrum.
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Mass Spectrometry: This is used to identify molecules and determines the mass of the organic molecule. It shows the breakdown of the original molecule and identifies the fragments.
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Description
This quiz covers the chemical properties of alcohols, including their structure, classifications, and reactions such as combustion and reaction with halogenating agents. It is designed to test your understanding of alcohol chemistry and their significance in organic reactions.