PHOrgChem (Lecture) | Module 10 (PART 1: AMINES, AMIDE, and NITRILES)

Amine

Derivatives of ammonia with one or more organic groups attached to nitrogen making them basic, and reactive.

Basic, and Reactive

Amines are derivatives of ammonia with one or more organic groups attached to nitrogen making them?

Amide

are formed when carboxylic acid’s OH group is replaced by a Nitrogen group creating strong bonds that are highly polar, found in proteins, and used in creating industrial and pharmaceutical products.

Protein

Amides are formed when carboxylic acid’s OH group is replaced by a Nitrogen group creating strong bonds that are highly polar, found in _______, and used in creating industrial and pharmaceutical products.

Highly Polar

Amides are formed when carboxylic acid’s OH group is replaced by a Nitrogen group creating strong bonds that are?

Nitrile

Containing a carbon triple-bonded to nitrogen, are highly polar and used creating many pharmaceutical and industrial products.

Amine, Amide, and Nitrile

Key building blocks in both living systems and chemical manufacture.

Amine

Organic compounds derived from ammonia (NH₃) where one or more hydrogen atoms are replaced by carbon containing groups.

Amine

Contain a nitrogen atom with a lone pair of electrons.

Lone Pair of Electrons

Contain a nitrogen atom with a?

Basic, and Reactive

Key Feature of Amine

Amine

Classified as primary (1°), secondary (2°), or tertiary (3°) based on the number of organic groups attached to nitrogen.

Amine

Act as bases and nucleophiles.

Bases, and Nucleophiles

Amines act as?

Amine

Found widely in biological systems and pharmaceuticals.

• Found everywhere in nature and in medicine, playing a crucial role in making proteins, neurotransmitters, and many types of drugs.

Polar

PHYSICAL PROPERTIES: Polarity of Amine

Nitrogen Atom's Lone Pair

PHYSICAL PROPERTIES: Amines are POLAR due to the _________________ of electrons, making it exhibit basicity

Basicity

PHYSICAL PROPERTIES: Amines are POLAR due to the nitrogen atom's lone pair of electrons, making it exhibit?

Hydrocarbons

PHYSICAL PROPERTIES: Amines typically have HIGHER boiling points than _________ of similar molecular weight

Alcohols

PHYSICAL PROPERTIES: Amines have LOWER boiling points than _________, because amines can only form hydrogen bonds by the hydrogen, and nitrogen interactions as opposed to alcohols which can hydrogen bond through both their hydroxyl group and nitrogen

Hydrogen, and Nitrogen Interactions

PHYSICAL PROPERTIES: Amines have LOWER boiling points than alcohol, because amines can only form hydrogen bonds by the ____________________ as opposed to alcohols which can hydrogen bond through both their hydroxyl group and nitrogen

Soluble

PHYSICAL PROPERTIES: Amines are in __________ water and polar solvents, especially smaller amines because of hydrogen bonding

Hydrogen Bonding

PHYSICAL PROPERTIES: Amines are SOLUBLE in water and polar solvents, especially smaller amines because of?

Methylamine, and Ethylamine

PHYSICAL PROPERTIES: Smaller amines such as __________, and __________ are generally soluble in water due to their ability to form hydrogen bonds with water molecules.

Decreases

PHYSICAL PROPERTIES: As the size of the amine increases, solubility _______, but they remain soluble in other polar solvents

Fishy, or Ammonia-Like

PHYSICAL PROPERTIES: Odor of Amines, especially for smaller amines

Smaller Amines

PHYSICAL PROPERTIES: Typically less dense than water for?

Heavier Amines

PHYSICAL PROPERTIES: Can be greater denser than water for larger for?

Ammonium Salts

CHEMICAL PROPERTIES: Amines act as bases due to the lone pair of electrons on nitrogen atoms, readily accepting protons (H⁺) from acid to form?

Bases

CHEMICAL PROPERTIES: Amines act as _____ due to the lone pair of electrons on nitrogen atoms, readily accepting protons (H⁺) from acid to form ammonium salts

Acids

CHEMICAL PROPERTIES: Amines react with ____ to form ammonium salts (e.g., amine + HCl → ammonium chloride).

Nucleophilic Substitution, and Addition Reactions

CHEMICAL PROPERTIES: Because of the basicity, Amines are highly nucleophilic and can participate in?

Highly Nucleophilic

CHEMICAL PROPERTIES: Because of the basicity, Amines are _______________ and can participate in nucleophilic substitution and addition reactions.

Imine

CHEMICAL PROPERTIES: Amines can interact with aldehydes and ketones to form ______, a reaction used in organic synthesis

Nitroso Compounds, Nitrites, or Ammonia Under Certain Conditions

CHEMICAL PROPERTIES: Amines can be oxidized to?

Schiff Bases

CHEMICAL PROPERTIES: Amines react with aldehydes and ketones to form imines (_________).

Aromatic Amines

CHEMICAL PROPERTIES: In _____________, the amine group can activate the aromatic ring for electrophilic substitution reactions

Electrophilic Substitution Reactions

CHEMICAL PROPERTIES: In aromatic amines, the amine group can activate the aromatic ring for?

Aromatic Amines

CHEMICAL PROPERTIES: In a____________, the lone pair on nitrogen, can donate electron density to the aromatic ring, activating it for electrophilic substitution reaction, making aromatic amines more reactive than simple hydrocarbons in reactions like halogenation and nitration.

Amphetamine

DRUGS: a stimulant used to treat ADHD and narcolepsy

Primary Amine

DRUGS: Functional Group of AMPHETAMINE that can affect its stability and effectiveness

Amphetamine

DRUGS: Primary amine makes it sensitive to oxidation. It can react with oxygen or oxidizing agents over time leading to degradation or loss of potency

Oxidation

DRUGS: Primary amine makes Amphetamine sensitive to __________.

Amphetamine

DRUGS: Primary amine on this drug is sensitive to oxidation—it can react with oxygen or oxidizing agents over time leading to degradation or loss of potency

Amphetamine

DRUGS: In acidic conditions, like stomach acid, the amine can get protonated (from NH2 to NH3), making it more water soluble but more chemically stable.

Acid Conditions

DRUGS: In these conditions, like stomach acid, the amine in Amphetamine can get protonated (from NH2 to NH3), making it more water soluble but more chemically stable.

Protonated

DRUGS: In acidic conditions, like stomach acid, the amine on Amphetamine can get ________ (from NH2 to NH3), making it more water soluble but more chemically stable.

More Chemically Stable

DRUGS: In acidic conditions, like stomach acid, the amine in Amphetamine can get protonated (from NH2 to NH3), making it more water soluble but?

Amphetamine

DRUGS: In basic conditions, the free amine form (NH2 form) is less stable.

Basic Conditions

DRUGS: In these conditions, Amphetamine—the free amine form (NH2 form) is less stable.

Less Stable

DRUGS: In basic conditions, the free amine in Amphetamine form (NH2 form) is?

Amphetamine

DRUGS: The free form or the non-protonated form (NH2) is lipophilic enough to cross the blood brain barrier reaching the brain where it acts

Free form, or non-protonated form

DRUGS: The _________, or ___________ (NH2) is lipophilic enough to cross the blood brain barrier reaching the brain where it acts (AMPHETAMINE)

Morphine

DRUGS: Contains amine functional group, which is a powerful painkiller or an opioid analgesic

Morphine

DRUGS: Tertiary amine functional group

Tertiary Amine

DRUGS: Functional Group of MORPHINE

Morphine

DRUGS: The tertiary amine is less reactive than secondary and primary amines, making this drug relatively stable against oxidation.

Less Reactive

DRUGS: The tertiary amine is _____________ than secondary and primary amines, making morphine relatively stable against oxidation.

Morphine

DRUGS: This is still sensitive to light, heat, and acidic or basic conditions but its amine group is not the weakest. The phenol groups and the double bonds are more reactive.

Phenol Groups, and Double Bonds

DRUGS: Morphine is still sensitive to light, heat, and acidic or basic conditions but its amine group is not the weakest. What groups are most reactive in Morphine?

Morphine

DRUGS: The tertiary amine can be protonated which carries a positive charge, at physiological pH, which can limit how easily this drug crosses the blood brain barrier compared to lipophilic or fat loving drugs.

Positive Charge

DRUGS: The tertiary amine in Morphine can be protonated which carries a _____________, at physiological pH, which can limit how easily this drug crosses the blood brain barrier compared to lipophilic or fat loving drugs.

Lower, and Less Complete

DRUGS: Morphine’s brain entry is ________, and _________ compared to drugs like heroin, which masked the amine with acetyl groups, making it more lipophilic and faster-acting.

Acetyl Groups

DRUGS: Morphine’s brain entry is lower and less complete compared to drugs like heroin, which masked the amine with ______________, making it more lipophilic and faster-acting.

Amide

Generally less basic than amines because the nitrogen lone pair is partially shared with the carbonyl group, making it less available to accept protons.

Amide

Found in proteins as peptide bonds and in many synthetic materials.

Amide

They are extremely important in nature as they create the peptide bonds that make the amino acids together to form proteins.

Amide

PHYSICAL PROPERTIES: Polar compounds due to the presence of the carbonyl group (C=O) and nitrogen (N-H) bond.

Carbonyl Group, and N-H Bonds

PHYSICAL PROPERTIES: Due to the polarity of the _______, and ________ that makes Amides polar, which significantly influences their physical and chemical properties

Amide

PHYSICAL PROPERTIES: Boiling point—Generally high, higher than amines and similar to carboxylic acids, and other atoms of the same molecular weight due to hydrogen bonding.

Polar

PHYSICAL PROPERTIES: Polarity of Amides

High Boiling Point

PHYSICAL PROPERTIES: One of the most notable features of amides

Hydrogen Bonding

PHYSICAL PROPERTIES: Boiling point—Generally high, higher than amines and similar to carboxylic acids, and other atoms of the same molecular weight due to?

Carboxylic Acid

PHYSICAL PROPERTIES: Amides have higher boiling point than amines and similar to?

Nitrogen Atom, and Oxygen Atom

PHYSICAL PROPERTIES: High boiling points and melting point because amides can form strong hydrogen bonds between the _______, and ________ of the carbonyl group, as well as between amide molecules.

Water, and Organic Solvents

PHYSICAL PROPERTIES: Amides are soluble in ______, and _________, due to their ability to form hydrogen bonds and engage with water molecules.

Soluble

PHYSICAL PROPERTIES: Amides are _________ in water and other polar solvents, due to their ability to form hydrogen bonds and engage with water molecules.

Amide

PHYSICAL PROPERTIES: Their solubility tends to decrease as the length of the alkyl group attached to the nitrogen increases.

Formamide, and Acetamide

PHYSICAL PROPERTIES: Smaller amides such as ______, and _______ are highly soluble in water.

Little to No Odor

PHYSICAL PROPERTIES: Amides often have _________________, though some may have a faint, characteristic smell.

Greater

PHYSICAL PROPERTIES: Usually have a density ______ than water, particularly for smaller amides.

Hydrolysis

CHEMICAL PROPERTIES: Amides can undergo this reaction to form carboxylic acids and amines (can be acid- or base-catalyzed)

Carboxylic acid, and Amine

CHEMICAL PROPERTIES: A hydrolysis reaction in which the amide bond is broken due to water, resulting in the formation of?

Acid, or Base

CHEMICAL PROPERTIES: Hydrolysis in Amides—this process can be catalyze by either?

Amines

CHEMICAL PROPERTIES: Amides can be reduced to _______ using reducing agents like lithium aluminum hydride (LiAlH₄)

Lithium aluminum hydride

CHEMICAL PROPERTIES: Reducing agent for amides to reduce it to amines

Reduction

CHEMICAL PROPERTIES: A transformation useful in chemical synthesis in Amides

Grignard reagents

CHEMICAL PROPERTIES: Amides react with _______________ to form ketones, which further demonstrate their utility in creating other important compounds.

Ketones

PHYSICAL PROPERTIES: Amides react with Grignard reagents to form ______, which further demonstrate their utility in creating other important compounds.

Dehydration

PHYSICAL PROPERTIES: Under certain conditions, amides can undergo ______ to form nitriles.

Nitriles

CHEMICAL PROPERTIES: Under certain conditions, amides can undergo dehydration to form?

Electrophilic Substitution

CHEMICAL PROPERTIES: Amides can participate in __________________, especially when aromatic, but this is less common than in nitriles or carboxylic acids.

Aromatic

CHEMICAL PROPERTIES: Amides can participate in electrophilic substitution, especially when ________, but this is less common than in nitriles or carboxylic acids.

Nitriles, or Carboxylic Acid

CHEMICAL PROPERTIES: Amides can participate in electrophilic substitution, especially when aromatic, but this is less common than in?

Hydrolysis, Reduction, Reaction with Grignard Reagents, and Electrophilic Substitution

Amides’ ability to engage in various chemical reactions including?

Acetaminophen, or Paracetamol

DRUGS: N-(4-HYDROXYPHENYL)ACETAMIDE is also known as?

Acetaminophen

DRUGS: PAIN RELIEVER or ANTIPYRETIC used reduce fever

Acetaminophen

DRUGS: Amide group contributes to the drug stability and plays a crucial role in effectiveness as a pain reliever and an antipyretic.

Relatively Stable

DRUGS: The amide group in Acetaminophen is ____________ under normal conditions.

Acetaminophen

DRUGS: It is not as reactive as an amino/amine group or carbonyl group in aldehydes or ketones, which makes this drug more resistant to hydrolysis and oxidation under typical storage conditions.