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Amines

A-Level AQA Chemistry

This pack of flashcards covers the chemistry of amines, including their nomenclature, basicity, and reactions with acids, halogenoalkanes, and acyl chlorides. It also discusses the preparation of primary, secondary, and tertiary amines, quaternary ammonium salts, and the role of excess reactants in synthesis reactions.

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"What are the base properties of primary aliphatic amines?"	"Primary aliphatic amines act as Bronsted-Lowry bases and readily accept a proton due to the lone pair of electrons on the nitrogen."
"Compare the base strength of primary amines and ammonia."	"Primary amines are stronger bases than ammonia due to the electron-releasing effect of alkyl groups, which makes the lone pair of electrons on the nitrogen more readily available."
"Why are secondary amines stronger bases than primary amines?"	"Secondary amines have more alkyl groups substituted onto the nitrogen atom, which increases the electron density on the nitrogen atom and makes them stronger bases."
"Why are tertiary amines and corresponding ammonium salts less soluble in water?"	"Tertiary amines and corresponding ammonium salts are less soluble in water, making them less strong bases than secondary amines. This point will not be examined."
"Why do primary aromatic amines not form basic solutions?"	"Primary aromatic amines do not form basic solutions because the lone pair of electrons on the nitrogen delocalizes with the ring of electrons in the benzene ring, making the nitrogen less able to accept protons."
"What is the overall order of base strength for amines?"	"Aromatic amines < ammonia < primary amines < tertiary amines < secondary amines."
"What happens when amines react with acids?"	"Amines react with acids to form ammonium salts."
"How can a basic buffer be made from an amine?"	"A basic buffer can be made by combining a weak base with a salt of that weak base, such as ammonia and ammonium chloride or methylamine and methylammonium chloride."
"Describe the process of forming a primary amine in a one-step reaction of halogenoalkanes with ammonia."	"The nucleophilic substitution reaction between halogenoalkanes and ammonia in a one-step reaction forms primary amines."
"What are the potential further reactions that can occur when a primary amine is formed?"	"Primary amines can react in a successive series of reactions forming secondary, tertiary amines, and quaternary ammonium salts."
"Why is the reaction between halogenoalkanes and ammonia not a good method for making a primary amine?"	"The further reactions that can occur would require the desired product to be separated from the other products."
"How can the further subsequent reactions be limited in the formation of primary amine?"	"Using an excess of ammonia can limit the further subsequent reactions and maximize the amount of primary amine formed."
"Describe the mechanism of the reaction between halogenoalkanes and ammonia to form a primary amine."	"In the first step, the nucleophile attacks the halogenoalkane to form an intermediate. In the second step, a second ammonia removes a proton from the intermediate to form the primary amine."
"What is the role of ammonia or the primary amine in the second step of the mechanism?"	"In the second step, either ammonia or the primary amine can remove a proton from the intermediate to form the amine."
"Describe the reaction mechanism for the formation of a tertiary amine from a secondary amine."	"The same reaction mechanism occurs with the secondary amine reacting to form a tertiary amine."
"Describe the overall scheme of reactions for forming a quaternary ammonium salt."	"The overall scheme involves reacting a halogenoalkane (RX) with excess ammonia to form a primary amine, and then reacting the primary amine with excess RX to form the quaternary ammonium salt."
"Define quaternary ammonium salt."	"A quaternary ammonium salt is a compound that contains a positively charged nitrogen atom (quaternary ammonium ion) and is often used as a cationic surfactant."
"How do quaternary salts function as surfactants?"	"Quaternary salts reduce the surface tension of liquids and are attracted to negatively charged surfaces, making them useful in fabric softeners, hair conditioners, and sewage flocculants."
"Describe the two-step reaction scheme for preparing amines from nitriles."	"Step 1: React halogenoalkane with KCN in aqueous ethanol to form nitrile. Step 2: Reduce the nitrile to amine using LiAIH4 in ether or by reducing with H2 using a Ni catalyst."
"What is a disadvantage of the two-step reaction for preparing amines from nitriles?"	"The two-step reaction may have a low yield."
"What is the product of reducing nitrobenzene?"	"The product of reducing nitrobenzene is phenylamine."
"What type of reaction occurs when aliphatic amines and phenylamine react with acyl chlorides and acid anhydrides?"	"A nucleophilic addition-elimination reaction occurs."
"What is the change in functional group when reacting acyl chlorides with primary amines?"	"The change in functional group is from acyl chloride to secondary amide."
"What is the change in functional group when reacting acid anhydrides with primary amines?"	"The change in functional group is from acid anhydride to secondary amide."

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What are the base properties of primary aliphatic amines?

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Primary aliphatic amines act as Bronsted-Lowry bases and readily accept a proton due to the lone pair of electrons on the nitrogen.

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[{"id":979338,"front":"What are the base properties of primary aliphatic amines?","back":"Primary aliphatic amines act as Bronsted-Lowry bases and readily accept a proton due to the lone pair of electrons on the nitrogen.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Primary aliphatic amines have a lone pair of electrons on the nitrogen atom, which allows them to act as Bronsted-Lowry bases. This means they can readily accept a proton from an acid. The aliphatic nature of these amines refers to the presence of alkyl groups attached to the nitrogen atom, which can affect their reactivity and physical properties.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979340,"front":"Compare the base strength of primary amines and ammonia.","back":"Primary amines are stronger bases than ammonia due to the electron-releasing effect of alkyl groups, which makes the lone pair of electrons on the nitrogen more readily available.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Primary amines are stronger bases than ammonia because the presence of alkyl groups in primary amines increases their electron-releasing effect. This effect makes the lone pair of electrons on the nitrogen atom more readily available, increasing the base strength.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979341,"front":"Why are secondary amines stronger bases than primary amines?","back":"Secondary amines have more alkyl groups substituted onto the nitrogen atom, which increases the electron density on the nitrogen atom and makes them stronger bases.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Secondary amines are stronger bases than primary amines due to the presence of more alkyl groups attached to the nitrogen atom. This increases the electron density on the nitrogen, enhancing its ability to donate a pair of electrons, thus making it a stronger base.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979344,"front":"Why are tertiary amines and corresponding ammonium salts less soluble in water?","back":"Tertiary amines and corresponding ammonium salts are less soluble in water, making them less strong bases than secondary amines. This point will not be examined.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Tertiary amines and corresponding ammonium salts are less soluble in water due to their molecular structure. The presence of three alkyl groups in tertiary amines reduces their ability to form hydrogen bonds with water molecules, making it harder for them to dissolve. This decreased solubility also affects the corresponding ammonium salts, as they are derived from the protonation of tertiary amines. This reduced solubility in water results in weaker interactions with water molecules, leading to lower solubility and weaker basicity compared to secondary amines.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979346,"front":"Why do primary aromatic amines not form basic solutions?","back":"Primary aromatic amines do not form basic solutions because the lone pair of electrons on the nitrogen delocalizes with the ring of electrons in the benzene ring, making the nitrogen less able to accept protons.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The delocalization of the lone pair of electrons on the nitrogen atom with the aromatic benzene ring reduces the availability of the lone pair for proton acceptance, hindering the formation of basic solutions. This phenomenon is specific to primary aromatic amines due to their molecular structure.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979348,"front":"What is the overall order of base strength for amines?","back":"Aromatic amines < ammonia < primary amines < tertiary amines < secondary amines.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The overall order of base strength for amines is determined by the availability of the lone pair of electrons on the nitrogen atom. This order is based on the ability of the amine to donate its lone pair of electrons to accept a proton, with aromatic amines being the weakest and secondary amines being stronger due to steric hindrance.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979349,"front":"What happens when amines react with acids?","back":"Amines react with acids to form ammonium salts.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"When amines react with acids, they undergo a process called protonation. This involves the amine molecule accepting a proton from the acid, resulting in the formation of an ammonium salt. This reaction is important in various biological and chemical processes, including the synthesis of pharmaceuticals and the functioning of neurotransmitters in the human body.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979351,"front":"How can a basic buffer be made from an amine?","back":"A basic buffer can be made by combining a weak base with a salt of that weak base, such as ammonia and ammonium chloride or methylamine and methylammonium chloride.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"A basic buffer can be created using an amine by combining it with a salt of the same weak base. This forms a solution that resists changes in pH when an acid or base is added. The salt provides the conjugate acid needed to maintain the buffer capacity.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979354,"front":"Describe the process of forming a primary amine in a one-step reaction of halogenoalkanes with ammonia.","back":"The nucleophilic substitution reaction between halogenoalkanes and ammonia in a one-step reaction forms primary amines.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The reaction involves the halogenoalkane acting as an electrophile, while ammonia acts as a nucleophile. The ammonia displaces the halogen atom, resulting in the formation of a primary amine. This one-step process is a type of nucleophilic substitution reaction.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979357,"front":"What are the potential further reactions that can occur when a primary amine is formed?","back":"Primary amines can react in a successive series of reactions forming secondary, tertiary amines, and quaternary ammonium salts.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"When a primary amine is formed, it can undergo further reactions due to its reactive nature. These reactions can lead to the formation of secondary and tertiary amines, as well as quaternary ammonium salts. This occurs through a series of successive reactions involving the primary amine group.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979359,"front":"Why is the reaction between halogenoalkanes and ammonia not a good method for making a primary amine?","back":"The further reactions that can occur would require the desired product to be separated from the other products.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The reaction between halogenoalkanes and ammonia is not a good method for making a primary amine because it can lead to further reactions, resulting in the formation of multiple products. Separating the desired primary amine from these other products becomes challenging.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979361,"front":"How can the further subsequent reactions be limited in the formation of primary amine?","back":"Using an excess of ammonia can limit the further subsequent reactions and maximize the amount of primary amine formed.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Excess ammonia limits further reactions by ensuring that the amine functional group is not further modified. This allows for the primary amine to be maximized in the reaction mixture. The excess ammonia outcompetes other reactants, favoring the formation of primary amines.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979362,"front":"Describe the mechanism of the reaction between halogenoalkanes and ammonia to form a primary amine.","back":"In the first step, the nucleophile attacks the halogenoalkane to form an intermediate. In the second step, a second ammonia removes a proton from the intermediate to form the primary amine.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The reaction between halogenoalkanes and ammonia to form a primary amine involves a two-step mechanism. In the first step, a nucleophile attacks the halogenoalkane, leading to the formation of an intermediate. In the second step, a second ammonia molecule acts as a base, removing a proton from the intermediate to yield the primary amine. This reaction is an example of nucleophilic substitution, where the halogen atom is replaced by the amino group.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979364,"front":"What is the role of ammonia or the primary amine in the second step of the mechanism?","back":"In the second step, either ammonia or the primary amine can remove a proton from the intermediate to form the amine.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"In the second step, ammonia or a primary amine acts as a base, abstracting a proton from the intermediate species. This deprotonation step is crucial for the formation of the final amine product in the reaction mechanism. Ammonia and primary amines are capable of serving as nucleophiles due to the lone pair of electrons on the nitrogen atom.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979368,"front":"Describe the reaction mechanism for the formation of a tertiary amine from a secondary amine.","back":"The same reaction mechanism occurs with the secondary amine reacting to form a tertiary amine.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The reaction mechanism for the formation of a tertiary amine from a secondary amine involves the secondary amine undergoing a substitution reaction with an alkyl halide or alkyl sulfonate to replace one of its alkyl groups with a new alkyl group, resulting in the formation of a tertiary amine. This process is known as quaternization and is a common method for synthesizing tertiary amines.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979370,"front":"Describe the overall scheme of reactions for forming a quaternary ammonium salt.","back":"The overall scheme involves reacting a halogenoalkane (RX) with excess ammonia to form a primary amine, and then reacting the primary amine with excess RX to form the quaternary ammonium salt.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The formation of a quaternary ammonium salt typically follows a two-step process involving the conversion of a halogenoalkane to a primary amine through reaction with excess ammonia, followed by the reaction of the primary amine with excess halogenoalkane to yield the quaternary ammonium salt. This method allows for the gradual substitution of halogen atoms with amine groups, ultimately leading to the formation of the quaternary salt.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979374,"front":"Define quaternary ammonium salt.","back":"A quaternary ammonium salt is a compound that contains a positively charged nitrogen atom (quaternary ammonium ion) and is often used as a cationic surfactant.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Quaternary ammonium salts are widely used in various industries due to their surfactant properties. They are positively charged, making them effective at interacting with negatively charged surfaces. This characteristic makes them valuable in applications such as disinfectants, fabric softeners, and pharmaceuticals.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979375,"front":"How do quaternary salts function as surfactants?","back":"Quaternary salts reduce the surface tension of liquids and are attracted to negatively charged surfaces, making them useful in fabric softeners, hair conditioners, and sewage flocculants.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Quaternary salts function as surfactants due to their ability to lower the surface tension of liquids and their attraction to negatively charged surfaces. This makes them effective in various applications such as fabric softeners, hair conditioners, and sewage flocculants.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979378,"front":"Describe the two-step reaction scheme for preparing amines from nitriles.","back":"Step 1: React halogenoalkane with KCN in aqueous ethanol to form nitrile. Step 2: Reduce the nitrile to amine using LiAIH4 in ether or by reducing with H2 using a Ni catalyst.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The first step involves the conversion of a halogenoalkane to a nitrile using KCN in aqueous ethanol. In the second step, the nitrile is reduced to an amine either by using LiAlH4 in ether or by hydrogenation with H2 using a Ni catalyst. These steps are crucial in synthesizing amines from nitriles efficiently.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979379,"front":"What is a disadvantage of the two-step reaction for preparing amines from nitriles?","back":"The two-step reaction may have a low yield.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"The two-step reaction for preparing amines from nitriles can result in a low yield due to the multiple reaction steps involved. This can lead to inefficiency in the overall process and potentially result in the loss of starting materials.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979381,"front":"What is the product of reducing nitrobenzene?","back":"The product of reducing nitrobenzene is phenylamine.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Nitrobenzene can be reduced to phenylamine through a process called nitro group reduction. This reaction involves the conversion of the nitro group (-NO2) to an amino group (-NH2), resulting in the formation of phenylamine as the final product.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979382,"front":"What type of reaction occurs when aliphatic amines and phenylamine react with acyl chlorides and acid anhydrides?","back":"A nucleophilic addition-elimination reaction occurs.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"Amines are nucleophiles due to the lone pair on nitrogen. Acyl chlorides and acid anhydrides are electrophiles. The reaction involves the nucleophile attacking the electrophile, followed by elimination of a leaving group, resulting in the formation of an amide. This process is known as nucleophilic addition-elimination.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979383,"front":"What is the change in functional group when reacting acyl chlorides with primary amines?","back":"The change in functional group is from acyl chloride to secondary amide.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"When acyl chlorides react with primary amines, the functional group changes from acyl chloride to a secondary amide. This transformation occurs through a nucleophilic acyl substitution reaction, where the amine replaces the chlorine atom in the acyl chloride, resulting in the formation of a secondary amide.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}},{"id":979384,"front":"What is the change in functional group when reacting acid anhydrides with primary amines?","back":"The change in functional group is from acid anhydride to secondary amide.","front_language":"English","back_language":"English","front_image":"","back_image":"","order":0,"explanation":"When acid anhydrides react with primary amines, the functional group undergoes a transformation. Acid anhydrides have a carbonyl group between two acyl groups, while primary amines have an amino group attached to a carbon atom. The reaction results in the formation of a new functional group called a secondary amide, where the carbonyl group is now bonded to two alkyl or aryl groups and an amino group. This change in functional group is due to the replacement of one of the acyl groups in the acid anhydride with the amino group from the primary amine.","deleted_at":null,"flashcard_deck_id":"e474a","original_id":null,"examMode":{"text":"","correct":"","incorrect":"","info":""}}]

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