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Questions and Answers
What kind of intermolecular forces are primarily responsible for the liquid state of alcohols?
What kind of intermolecular forces are primarily responsible for the liquid state of alcohols?
- Hydrogen bonds (correct)
- Ionic bonds
- Covalent bonds
- Van der Waals forces
How does the solubility of alcohols change with an increase in the length of the carbon chain?
How does the solubility of alcohols change with an increase in the length of the carbon chain?
- Solubility in water becomes very high
- Solubility in water remains constant
- Solubility in water decreases (correct)
- Solubility in water increases significantly
Which characteristic is true for alcohols in biological systems?
Which characteristic is true for alcohols in biological systems?
- They serve as a primary source of energy
- They are highly toxic and not soluble in water
- They inhibit all enzyme activity
- They can act as both weak acids and weak bases (correct)
What is the product formed when a primary alcohol undergoes oxidation?
What is the product formed when a primary alcohol undergoes oxidation?
Which type of alcohol is most resistant to oxidation?
Which type of alcohol is most resistant to oxidation?
What characteristic of low molecular mass aldehydes and ketones contributes to their solubility in water?
What characteristic of low molecular mass aldehydes and ketones contributes to their solubility in water?
Which statement accurately describes the reactivity of aldehydes compared to ketones?
Which statement accurately describes the reactivity of aldehydes compared to ketones?
In the reaction between a nucleophile and an aldehyde, what is formed after the nucleophile donates its electron pair?
In the reaction between a nucleophile and an aldehyde, what is formed after the nucleophile donates its electron pair?
Why are ketones generally stable to oxidation, unlike aldehydes?
Why are ketones generally stable to oxidation, unlike aldehydes?
What effect does adding an acid have on the reactivity of the C=O bond in aldehydes and ketones?
What effect does adding an acid have on the reactivity of the C=O bond in aldehydes and ketones?
After reduction, what is the product obtained from aldehydes and ketones?
After reduction, what is the product obtained from aldehydes and ketones?
Which reaction is characterized by the conversion of a C=O bond to a C=N bond?
Which reaction is characterized by the conversion of a C=O bond to a C=N bond?
What role do aldehydes and ketones play in biological systems?
What role do aldehydes and ketones play in biological systems?
What is the reason for supplying many acidic drugs as salts?
What is the reason for supplying many acidic drugs as salts?
Which statement best describes the boiling points of esters compared to amides?
Which statement best describes the boiling points of esters compared to amides?
What factor decreases the water solubility of esters and amides?
What factor decreases the water solubility of esters and amides?
What type of reaction primarily characterizes the reactivity of carboxylic acids?
What type of reaction primarily characterizes the reactivity of carboxylic acids?
What is true about the oxidation of carboxylic acids under normal conditions?
What is true about the oxidation of carboxylic acids under normal conditions?
Which of the following statements about amides is correct?
Which of the following statements about amides is correct?
How does the ability to form hydrogen bonds affect the solubility of amides in water?
How does the ability to form hydrogen bonds affect the solubility of amides in water?
What is the significance of hydrolysis in the context of esters and amides?
What is the significance of hydrolysis in the context of esters and amides?
What is the general formula for alcohols and how does it contribute to their physical properties?
What is the general formula for alcohols and how does it contribute to their physical properties?
Explain the trend in water solubility of alcohols as the R group increases in length.
Explain the trend in water solubility of alcohols as the R group increases in length.
Describe the oxidation products of a primary alcohol and a secondary alcohol.
Describe the oxidation products of a primary alcohol and a secondary alcohol.
Why are tertiary alcohols resistant to oxidation?
Why are tertiary alcohols resistant to oxidation?
What unique characteristic of alcohols contributes to their weak acidity and basicity?
What unique characteristic of alcohols contributes to their weak acidity and basicity?
Why are amides considered neutral compared to amines?
Why are amides considered neutral compared to amines?
What are cyclic amides and how are they referred to?
What are cyclic amides and how are they referred to?
Explain the trend in base strength among primary, secondary, and tertiary amines.
Explain the trend in base strength among primary, secondary, and tertiary amines.
How do low molecular mass amines interact with water?
How do low molecular mass amines interact with water?
What is the primary consequence of hydrolysis reactions for amides during storage?
What is the primary consequence of hydrolysis reactions for amides during storage?
Describe the physical state of amines with low molecular mass at room temperature.
Describe the physical state of amines with low molecular mass at room temperature.
What is the general structural formula of a primary amine?
What is the general structural formula of a primary amine?
Why are amides resistant to oxidation under normal conditions?
Why are amides resistant to oxidation under normal conditions?
What is formed when an alcohol reacts with an acid?
What is formed when an alcohol reacts with an acid?
Why are low molecular mass ethers soluble in water?
Why are low molecular mass ethers soluble in water?
What is the general formula for ethers?
What is the general formula for ethers?
What is a significant concern regarding the storage of diethyl ether?
What is a significant concern regarding the storage of diethyl ether?
What distinguishes aldehydes and ketones from alkenes in terms of bonding?
What distinguishes aldehydes and ketones from alkenes in terms of bonding?
What type of bonds do ethers form with each other?
What type of bonds do ethers form with each other?
How does the presence of the carbonyl group impact the physical properties of aldehydes and ketones?
How does the presence of the carbonyl group impact the physical properties of aldehydes and ketones?
What type of esters are biologically important, and why?
What type of esters are biologically important, and why?
What is the primary advantage of supplying acidic drugs as salts?
What is the primary advantage of supplying acidic drugs as salts?
What limits the solubility of higher molecular mass aldehydes and ketones in water?
What limits the solubility of higher molecular mass aldehydes and ketones in water?
Why can aldehydes undergo oxidation while ketones cannot?
Why can aldehydes undergo oxidation while ketones cannot?
What type of mechanism do carboxylic acids mainly undergo in reactions with nucleophiles?
What type of mechanism do carboxylic acids mainly undergo in reactions with nucleophiles?
How do the boiling points of esters compare to those of amides, and why?
How do the boiling points of esters compare to those of amides, and why?
In the nucleophilic addition reaction of aldehydes, which atom does the nucleophile typically attack?
In the nucleophilic addition reaction of aldehydes, which atom does the nucleophile typically attack?
What type of reaction occurs when an amine acts as a nucleophile with aldehydes?
What type of reaction occurs when an amine acts as a nucleophile with aldehydes?
What is the reactivity trend of amides compared to esters?
What is the reactivity trend of amides compared to esters?
What is the main product of the reaction between an alcohol and a carboxylic acid?
What is the main product of the reaction between an alcohol and a carboxylic acid?
How do low molecular mass aldehydes and ketones interact with water?
How do low molecular mass aldehydes and ketones interact with water?
What is the main product of the reduction reaction of aldehydes?
What is the main product of the reduction reaction of aldehydes?
What role does hydrolysis play in the context of esters and amides?
What role does hydrolysis play in the context of esters and amides?
Why are carboxylic acids more stable than aldehydes under normal storage conditions?
Why are carboxylic acids more stable than aldehydes under normal storage conditions?
What role does protonation of the carbonyl oxygen play in aldehyde reactivity?
What role does protonation of the carbonyl oxygen play in aldehyde reactivity?
How does the carbon chain length affect the water solubility of esters and amides?
How does the carbon chain length affect the water solubility of esters and amides?
In aqueous solutions, how do sugars form their cyclic structures involving aldehydes?
In aqueous solutions, how do sugars form their cyclic structures involving aldehydes?
How do metal hydrides like LiAlH4 selectively reduce C=O groups but not C=C double bonds?
How do metal hydrides like LiAlH4 selectively reduce C=O groups but not C=C double bonds?
What is the significance of the acyl group in carboxylic acids?
What is the significance of the acyl group in carboxylic acids?
Explain why low molecular mass carboxylic acids are highly soluble in water.
Explain why low molecular mass carboxylic acids are highly soluble in water.
What effect does an electron withdrawing group have on the strength of carboxylic acids?
What effect does an electron withdrawing group have on the strength of carboxylic acids?
How does the presence of electron donating groups affect the acidity of carboxylic acids?
How does the presence of electron donating groups affect the acidity of carboxylic acids?
What happens to aldehydes when they are exposed to air compared to ketones?
What happens to aldehydes when they are exposed to air compared to ketones?
Describe the process of neutralizing a carboxylic acid using a base.
Describe the process of neutralizing a carboxylic acid using a base.
What determines the physical properties of carboxylic acids, such as their state at room temperature?
What determines the physical properties of carboxylic acids, such as their state at room temperature?
Flashcards
Solubility of Aldehydes/Ketones
Solubility of Aldehydes/Ketones
Low molecular weight aldehydes and ketones are soluble in water due to hydrogen bonding with water.
Reactivity of Aldehydes/Ketones
Reactivity of Aldehydes/Ketones
Aldehydes and ketones react with nucleophiles through nucleophilic addition reactions. The C=O bond is the reactive site.
Nucleophilic Addition Reaction
Nucleophilic Addition Reaction
A reaction where a nucleophile gives an electron pair to the positive carbon of the carbonyl which leads to the formation of a new single bond.
Oxidation of Aldehydes
Oxidation of Aldehydes
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Ketone Oxidation
Ketone Oxidation
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Reduction of Aldehydes/Ketones
Reduction of Aldehydes/Ketones
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Cyclic Sugar Formation
Cyclic Sugar Formation
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Importance of carbonyl reactions
Importance of carbonyl reactions
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Alcohol general formula
Alcohol general formula
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Alcohol property related to solubility
Alcohol property related to solubility
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1° alcohol oxidation
1° alcohol oxidation
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2° alcohol oxidation
2° alcohol oxidation
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3° alcohol oxidation
3° alcohol oxidation
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Salt Formation of Carboxylic Acids
Salt Formation of Carboxylic Acids
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Nucleophilic Substitution in Acyl Groups
Nucleophilic Substitution in Acyl Groups
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Ester Formation
Ester Formation
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Oxidation Resistance of Carboxylic Acids
Oxidation Resistance of Carboxylic Acids
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Amide Classification
Amide Classification
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Boiling Point Difference Between Esters and Amides
Boiling Point Difference Between Esters and Amides
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Solubility of Esters and Amides
Solubility of Esters and Amides
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Reactivity of Esters & Amides: Nucleophilic Substitution
Reactivity of Esters & Amides: Nucleophilic Substitution
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Amide Basicity
Amide Basicity
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Lactams
Lactams
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Amines Structure
Amines Structure
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Amine Solubility
Amine Solubility
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Amines as Bases
Amines as Bases
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Base Strength Order
Base Strength Order
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Steric Hindrance in Amines
Steric Hindrance in Amines
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Amide Oxidation Resistance
Amide Oxidation Resistance
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Alcohol Solubility
Alcohol Solubility
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Aldehyde Solubility
Aldehyde Solubility
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Ketone Solubility
Ketone Solubility
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Nucleophilic Addition
Nucleophilic Addition
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Amine Reaction Importance
Amine Reaction Importance
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Aldehyde Oxidation
Aldehyde Oxidation
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Aldehyde/Ketone Reduction
Aldehyde/Ketone Reduction
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Phosphate Esters
Phosphate Esters
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Ether General Formula
Ether General Formula
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Ether Solubility
Ether Solubility
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Ether Reactivity
Ether Reactivity
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Aldehyde and Ketone Structure
Aldehyde and Ketone Structure
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Aldehyde and Ketone Properties
Aldehyde and Ketone Properties
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Storage of Ethers
Storage of Ethers
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LiAlH4
LiAlH4
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Hydride Ion Attack
Hydride Ion Attack
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Selective Reduction
Selective Reduction
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Carboxylic Acid Formula
Carboxylic Acid Formula
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Acyl Group
Acyl Group
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Carboxylic Acid Acidity
Carboxylic Acid Acidity
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Why are carboxylic acids resistant to oxidation?
Why are carboxylic acids resistant to oxidation?
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Electron Withdrawing Group
Electron Withdrawing Group
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What is the main reaction type for acyl groups?
What is the main reaction type for acyl groups?
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Salt Formation
Salt Formation
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What is the structure of an ester?
What is the structure of an ester?
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What is the difference in boiling point between esters and amides?
What is the difference in boiling point between esters and amides?
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What is a 1º, 2º, 3º amide?
What is a 1º, 2º, 3º amide?
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Why are amides less reactive than esters?
Why are amides less reactive than esters?
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What is the main pharmaceutical importance of hydrolysis?
What is the main pharmaceutical importance of hydrolysis?
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Study Notes
Organic Functional Groups - Lecture 4
- Alcohols:
- General formula: R-OH
- Physical properties: Form H-bonds between molecules, even low molar mass alcohols are liquids. H-bonds with water, so lower molar mass alcohols are very soluble in water. Longer chains result in decreased water solubility.
- Weakly basic and weakly acidic.
- Reversible protonation by strong acids.
- Dissociate slightly in dilute aqueous solution by donating a proton to water.
- Reactivity/Stability: Stable under normal conditions but reactive with other compounds, particularly mild oxidizing agents. Oxidation type depends on the alcohol's degree (1°, 2°, or 3°).
- 1° alcohols oxidize to aldehydes, then to carboxylic acids.
- 2° alcohols oxidize to ketones..
- 3° alcohols are resistant to oxidation
- Ester formation: Reaction with organic acids results in esters. Biologically, phosphate esters are important.
Acidity Constants of Alcohols and Phenols
- Specific examples of pKa values for various alcohols and phenols are provided. This table shows the increasing acidity from CH3CH2OH to 2,4,6-Trinitrophenol, with decreasing pKa values.
Reactivity/Stability of Alcohols
- Stable under normal conditions, but reactive towards other compounds.
- Significant reaction with mild oxidizing agents. Oxidation type depends on 1°, 2°, or 3° alcohol.
Ethers
- General formula: R-O-R
- Physical properties: Cannot form H-bonds amongst themselves, thus low RMM ethers are gases/liquids at room temperature. Can form H-bonds with water, so low RMM ethers are soluble in water. Solubility decreases with increasing chain length.
- Reactivity/Stability: Relatively unreactive and are commonly used as solvents (e.g., diethyl ether). Like alkenes, they can form peroxides in air. Storing in an airtight container is recommended to avoid peroxide formation.
Aldehydes and Ketones
- Both contain a carbonyl (C=O) group.
- Two R groups = ketone
- At least one H = aldehyde
- Physical properties: Polar C=O bond leads to intermolecular attractions but not H-bonds. Liquids at room temperature. Lower RMM compounds are water-soluble. Solubility decreases with increasing molecular mass.
- Reactivity/stability: React with nucleophiles via nucleophilic addition reactions/Can be oxidized (aldehydes only).
- When nucleophile is an alcohol, reaction products are hemiacetals (aldehydes) or hemiketals (ketones). These reactions are important in sugar chemistry.
- Also important in drug-receptor combinations and enzyme reactions.
Carboxylic Acids (Alkanoic Acids)
- Formula: R-COOH
- Physical properties: Long chains are solids at room temperature, while lower RMM are liquids. Considerable H-bonding results in high boiling points and solubility in water. Low RMM compounds are soluble in water, while higher RMM solubility decreases with increasing chain length.
- Acidic nature: Donate protons (H+) to more basic substances (e.g., water). Carboxylate ion is stabilized by resonance.
- Relative strength: Depends on R groups. Electron-withdrawing groups increase acid strength, while electron-donating groups decrease it..
Salt Formation
- An acid can be neutralized by reacting with a base (e.g., NaOH) to form a salt.
- This process can significantly increase the water solubility of insoluble carboxylic acids, which is practically useful in medicine.
Reactivity of Carboxylic Acids
- Reactions involving acyl (R-C=O) groups are usually nucleophilic substitutions.
- When reacting with an alcohol, the resulting product is an ester.
Oxidation of Carboxylic Acids
- Under normal conditions, carboxylic acids are resistant to oxidation. They are significantly more stable to oxidation than aldehydes.
Esters and Amides
- General Structure
- Ester: R-C(=O)-O-R'
- Amide: R-C(=O)-N-R1R2
- Esters and amides have different boiling points and water solubility.
- Amides:
- Can form hydrogen bonds, allowing higher boiling points than esters.
- Generally, less reactive than esters, with significant reactions involving nucleophilic substitutions when acting as the carboxylic acid derivative group.
Amines
- General Structure: R-NH2 (primary), R-NHR (secondary), R-NR2 (tertiary).
- Properties:
- Lower molar mass amines are gases at room temperature
- Higher molar mass amines tend to be liquids
- Low RMM amines are soluble in water, solubility decreases with increasing chain length (becomes more "alkane-like")
- Amines as Bases:
- Take up protons from acid due to the pair of electrons on the N atom.
- Relative base strength differs in the 1°, 2°, and 3° amines. Steric hindrance can affect the strength.
Storage Considerations
- Aldehydes and ketones require storage in a cool dry location
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Description
This quiz covers the properties and reactions of alcohols, including their general formula, physical properties, and reactivity with other compounds. Key concepts such as acidity constants, protonation, and the formation of esters are also explored. Test your knowledge of these fundamental aspects of organic chemistry!