Carboxylic Acids and Derivatives Flashcards

Describe the change in functional group when acid anhydride reacts with primary amine.

The acid anhydride is converted into a secondary amide.

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Describe the change in functional group when acid anhydride reacts with primary amine.	The acid anhydride is converted into a secondary amide.
Is biodiesel considered carbon-neutral?	Biodiesel produced from vegetable oils can be considered carbon-neutral as the carbon dioxide released during combustion would have been extracted from the air during photosynthesis.
What factors can affect the carbon neutrality of biodiesel?	Factors such as energy sources used for extraction, processing, and production can affect the carbon neutrality of biodiesel, as well as the impact on land available for food production.
Describe the reactivity of acyl chlorides compared to carboxylic acids.	Acyl chlorides are much more reactive than carboxylic acids.
What are the main products formed when acyl chlorides react with water?	The main products are carboxylic acid and hydrogen chloride gas.
What are the main products formed when acid anhydrides react with water?	The main products are two molecules of carboxylic acid.
Define leaving groups in the context of acyl chlorides and acid anhydrides.	The Cl and -OCOCH3 groups are considered good leaving groups due to their delocalization.
What is the advantage of using acid anhydrides instead of carboxylic acids to make esters?	The reaction is much quicker and not reversible.
Describe the mechanism of nucleophilic addition-elimination in the context of acyl chlorides and acid anhydrides.	Nucleophile adds to the carbonyl carbon, followed by elimination of a leaving group to form a new functional group.
Describe the change in functional group when acyl chloride reacts with ammonia.	The acyl chloride is converted into a primary amide.
What is the observation when acyl chloride reacts with ammonia?	White smoke of NH4Cl is given off.
Define nucleophilic addition.	It is a reaction in which a nucleophile attacks an electrophile, resulting in the addition of a new group to the electrophile.
Describe the process of converting vegetable oils into biodiesel.	Vegetable oils can be converted into biodiesel by reacting with methanol in the presence of a strong alkali catalyst.
What are the conditions for the reaction between acid anhydride and primary amine?	The reaction occurs at room temperature.
Do primary amines undergo nucleophilic addition or elimination when reacting with acid anhydride?	Primary amines undergo nucleophilic addition.
Describe the process of making aspirin.	Aspirin is made by reacting hydroxybenzoic acid with ethanoic anhydride to form an ester. Ethanoic anhydride is used instead of acid chlorides due to its cost-effectiveness, lower corrosiveness, and reduced vulnerability to hydrolysis.
What is the purpose of recrystallization in the purification of aspirin?	Recrystallization is used to purify aspirin by dissolving the impure compound in a hot solvent, filtering out insoluble impurities, cooling the solution to allow crystals to form, washing the crystals to remove soluble impurities, and drying them.
How does the use of ethanoic anhydride in making aspirin differ from acid chlorides?	Ethanoic anhydride is preferred over acid chlorides in making aspirin due to its lower cost, reduced corrosiveness, decreased vulnerability to hydrolysis, and improved safety.
Define recrystallization.	Recrystallization is a purification technique that involves dissolving an impure compound in a hot solvent, allowing it to cool to form crystals, and separating the crystals from impurities through filtration.
What is the purpose of washing the crystals with distilled water during recrystallization?	Washing the crystals with distilled water helps remove soluble impurities that may be present on the surface of the crystals, improving their purity.
Describe one way of testing for the degree of purity.	Determining the melting point or melting range of the sample.
What can cause the melting point of a sample to be lowered?	Impurities, including solvent from the recrystallization process.
How can the melting point of a sample be measured?	Using an electronic melting point machine or a practical setup with a capillary tube and a thermometer immersed in heating oil.
What can be used to verify the degree of purity of a sample?	Comparing the experimentally determined melting point value with one quoted in a data source.
What can cause an error in determining the melting point of a sample?	If the temperature on the thermometer is not the same as the temperature in the actual sample tube.
Explain the process of hydrolysis of esters with sodium hydroxide.	When an ester is hydrolysed with sodium hydroxide, it forms a carboxylic acid salt and an alcohol. This reaction goes to completion and is not reversible.
What is the name of a carboxylic acid with carboxylic acid groups on both ends of the chain?	It is called a dioic acid.
Define solubility of carboxylic acids in water.	Carboxylic acids are weak acids that dissolve in water and slightly dissociate.
How are carboxylic acid salts stabilized?	Carboxylic acid salts are stabilized by delocalization, which makes dissociation more likely.
Describe the strength of carboxylic acids with increasing chain length.	Increasing chain length pushes electron density onto the COO- ion, making it more negative and the acid less strong.
What effect do alkyl groups have on the acidity of carboxylic acids?	Alkyl groups are electron-releasing and decrease the acidity of carboxylic acids.
How does the presence of chlorine atoms affect the acidity of carboxylic acids?	Chlorine atoms are electron-withdrawing and increase the acidity of carboxylic acids.
What is the purpose of delocalization in carboxylic acid salts?	Delocalization stabilizes the carboxylic acid salts, making dissociation more likely.
Describe the salt formation reactions of carboxylic acids.	Carboxylic acids can form salts with metals, alkalis, and carbonates.
What is the product of the reaction between carboxylic acid and metal (Na)?	The product is salt and hydrogen gas.
How can the effervescence caused by the reaction between carboxylic acids and solid NaCO or aqueous NaHCO be used?	It can be used as a functional group test for carboxylic acids.
Define esterification.	Esterification is the reaction between carboxylic acids and alcohols, in the presence of a strong acid catalyst, to form esters and water.
What are some uses of esters?	Esters can be used in perfumes, flavorings, solvents for polar organic substances, and as plasticizers for polymers.
Describe the process of hydrolysis of esters with acid.	When an ester is hydrolysed with acid, a carboxylic acid and an alcohol are formed. This reaction is reversible and does not give a good yield of the products.
What are the reagents and conditions required for hydrolysis of esters with acid?	Reagents: dilute acid (HCI), Conditions: heat under reflux.
Describe the naming convention for carboxylic acids.	Carboxylic acids are named by replacing the -e ending of the corresponding alkane with -oic acid.
What are the reagents and conditions required for hydrolysis of esters with sodium hydroxide?	Reagents: dilute sodium hydroxide, Conditions: heat under reflux.
How can the ester be completely hydrolysed during the reaction with sodium hydroxide?	Using excess sodium hydroxide will ensure the ester is completely hydrolysed.
What happens when a strong acid, such as hydrochloric acid, is added to the carboxylic acid salt formed during hydrolysis with sodium hydroxide?	The salt is converted back to the carboxylic acid form.
Describe the practical method for the formation of esters and hydrolysis of esters.	Both formation of esters and hydrolysis of esters can be done by heating under reflux. Most esters are liquids, so they can be purified using the steps outlined in practical guide AQA required practical 10 purification of an organic liquid.
How can ethyl benzoate be hydrolysed?	Ethyl benzoate can be hydrolysed by heating under reflux with sodium hydroxide for 30 minutes.
What is the product formed when ethyl benzoate is hydrolysed with sodium hydroxide?	Sodium benzoate is formed.
How can benzoic acid be obtained from the reaction of ethyl benzoate with sodium hydroxide?	After the reaction is complete, hydrochloric acid is added to the mixture, resulting in the formation of a precipitate of benzoic acid that can be filtered off using suction filtration.
Why is benzoic acid insoluble in water?	Benzoic acid is insoluble in water because even though the polar COOH group can form hydrogen bonds, the benzene ring is non-polar.
Describe the process of hydrolysis of vegetable oils and animal fats.	Hydrolysis of vegetable oils and animal fats produces glycerol and long chain carboxylic (fatty) acids.
What are the components of soap?	Soap is composed of glycerol and long chain carboxylic (fatty) acids.
Define glycerol.	Glycerol, also known as propane-1,2,3-triol, is a compound that forms hydrogen bonds easily and is soluble in water.
How do long chain carboxylic acids act as soaps?	Long chain carboxylic acids, produced by the hydrolysis of fats, act as soaps by having a hydrophilic CO2 end that mixes with water and a hydrophobic hydrocarbon chain that mixes with grease.

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