1 / 53

Classification of Amines

Amines. Classification of Amines Amines are basic nitrogen-containing compounds that are derivatives of ammonia. Amines are classified as: Primary (the nitrogen atom has one hydrocarbon group directly attached) Secondary (the nitrogen atom has two hydrocarbon groups directly attached)

sol
Télécharger la présentation

Classification of Amines

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Amines • Classification of Amines • Amines are basic nitrogen-containing compounds that are derivatives of ammonia. Amines are classified as: • Primary(the nitrogen atom has one hydrocarbon group directly attached) • Secondary(the nitrogen atom has two hydrocarbon groups directly attached) • Tertiary(the nitrogen atom has three hydrocarbon groups directly attached). 1

  2. Amines: Nomenclature and Physical Properties Examples of primary (1o), secondary (2o) and tertiary (3o) amines are shown here. 2

  3. Classify the following amines as 1o, 2o or 3o. Your Turn! 3

  4. Classify the following amines as 1o, 2o or 3o. Your Turn! 4

  5. Amines: Nomenclature and Physical Properties • IUPAC Rules for Naming Amines • Name the longest continuous carbon chain containing the amine group. The carbon atom attached to the amine group is the #1 carbon atom. • Drop –e from the corresponding alkane and add the suffix –amine. 5

  6. Amines: Nomenclature and Physical Properties Here are some examples of primary amines. 6

  7. Amines: Nomenclature and Physical Properties 3. Use a prefix with a capital N (italicized) if the amine nitrogen atom has an alkyl group or other group attached (2o and 3o amines). 7

  8. Amines: Nomenclature and Physical Properties Simple amines are most often referred to by their common names. The common names for aliphatic amines are formed by naming the alkyl group or groups attached to the nitrogen atom, followed by the ending –amine. 8

  9. Amines: Nomenclature and Physical Properties The common names of some amines are shown here. 9

  10. Amines: Nomenclature and Physical Properties The most important aromatic amine is aniline (C6H5NH2). Derivatives are named as substituted anilines. 10

  11. Give names for the following amines. Your Turn! 11

  12. Give names for the following amines. Your Turn! 12

  13. Chemical Properties of Amines Alkaline Properties of Amines Amines resemble ammonia in their reactions. Amines are bases, and like ammonia, produce OH- ions in water สารละลายเป็นเบส 17

  14. Chemical Properties of Amines Salt Formation Because amines are weak bases, they react with strong acids to form ammonium salts. Methylamine for example reacts with strong acid yielding the corresponding methylamoniumsalt. 18

  15. Chemical Properties of Amines Methylammonium chloride is a white crystalline solid made up of methylammonium ions, CH3NH3+, and chloride ions, Cl-. Many amines or amino compounds are more stable in the form of the hydrochloride salt. When the free amine is wanted, the HCl is neutralized to liberate the free amine. 19

  16. Sources and Uses of Selected Amines • Biogenic aminesare derived from amino acids and act as neurotransmitters and hormones in animals. • GABA (γ-aminobutyric acid) slows nerve action and can bring relaxation. 20

  17. Sources and Uses of Selected Amines Amphetamines are designed to mimic the action of biogenic amines and act as stimulants. They are used to treat depression, narcolepsy, and obesity. The most widely abused amphetamine is methamphetamine, commonly called “speed.” 21

  18. Sources and Uses of Selected Amines Barbiturates are another class of drugs that are amines. These drugs are classified as sedatives and depress the activity of brain cells. An example is pentobarbital. 22

  19. Sources and Uses of Selected Amines Basic compounds that are derived from plants and show physiological activity are known as alkaloids. These substances are usually amines. Nicotine, an alkaloid derived from tobacco leaves, acts to stimulate the nervous system. 23

  20. Sources and Uses of Selected Amines Coffee beans and tea leaves contain caffeine, an alkaloid stimulant. 24

  21. Sources and Uses of Selected Amines These drugs are classified as narcotics because they produce physical addiction, and they are strictly regulated by federal law. An example is methadone. 25

  22. Sources and Uses of Selected Amines Another common narcotic alkaloid, cocaine, is obtained from the leaves of the coca plant. 27

  23. Amides Amides

  24. Amides Amides are derivatives of carboxylic acids in which a nitrogen group (–NH2) replaces the –OH group of carboxylic acids. O O |||| CH3—C—OHCH3—C—NH2

  25. Preparation of Amides Amides are produced by reacting a carboxylic acid with ammonia or a 1 or 2 amine with heat.

  26. Amides: Nomenclature and Physical Properties IUPAC names for amides are formed from the IUPAC names of carboxylic acids. Here are two examples. 33

  27. Amides: Nomenclature and Physical Properties The common names for amides are formed from the common names of carboxylic acids. 34

  28. 35

  29. Polyamides are condensation polymers that contain repeating amide linkages as shown here. Polyamides: Condensation Polymers 36

  30. Polyamides: Condensation Polymers Polyamides are either synthetic like Nylon-66 or are biological like the protein chymotrypsin. The structure of chymotrypsin is shown below. 37

  31. Polyamides: Condensation Polymers The structure of synthetic Nylon-66 is shown here. 38

  32. Urea is a simple diamide that is excreted in urine. Urea is the metabolite the body uses to excrete toxic ammonia. Urea Urea is a white solid that melts at 133 C. It is very soluble in water. 39

  33. Naming Amides • For IUPAC naming, the -oic acid from the carboxylic acid nameending is replacedwith-amide • For common names, the -ic acid from the carboxylic acid name ending is replaced with -amide O  methanamide (IUPAC) H—C—NH2 formamide (common) O  propanamide (IUPAC) CH3—CH2—C—NH2 propionamide(common)

  34. Aromatic Amide The aromatic amine is benzamide. Benzamide

  35. Learning Check Give the IUPAC and common names for the following. O  A. CH3–CH2–CH2–C–NH2 O H  │ B. CH3–C–N–CH2–CH3

  36. Solution O  A. CH3–CH2–CH2–C–NH2 butanamide (IUPAC) butryamide (common) O H  │ B. CH3–C–N–CH2–CH3 N-ethylethanamide (IUPAC) N-ethylacetamide (common)

  37. Learning Check Draw the structures of the following. A. pentanamide B. N-methylbutyramide

  38. Solution A. pentanamide O  CH3–CH2–CH2–CH2–C–NH2 B. N-methylbutyramide O  CH3–CH2–CH2–C–NH–CH3

  39. Some Amides in Health and Medicine • Urea is the end product of protein metabolism. • Saccharin is an artificial sweetener. • Some amides, such as phenobarbital (Luminal) and pentobarbital (Nembutal), are barbiturates. • Acetaminophen is used to reduce fever and pain.

  40. Some Amides in Health and Medicine

  41. Solubility of Amides Amides with one to five carbon atoms are soluble in water because they can form hydrogen bonds with water molecules. Hydrogen bonding effects are diminished when molecules have more than five carbon atoms, therefore reducing solubility.

  42. Hydrolysis of Amides Amides undergo • acid hydrolysis to produce a carboxylic acid and an ammonium salt • base hydrolysisto produce the salt of a carboxylic acid and an amine or ammonia

  43. Hydrolysis Reactions

More Related