Ch 16 Amines Organic and Biochemsity
Amines Section 16.1 Introduction itrogen found in amine group is the fourth most common element in organic chemistry Known for their basicity
Section 16.2 Classification and Structure Primary 1⁰ R 2 Secondary 2⁰ Tertiary 3⁰ R R R R R
Aliphatic Amines All carbon groups bonded to the nitrogen are ALKYL groups Aromatic Amines One or more groups bonded to the nitrogen are ARYL groups eterocyclic Amines itrogen is a part of the RIG
Identify these examples: C 3 2 C 3 C 3 1⁰ Aromatic Amine 2⁰ Aromatic Amine 3⁰ Aliphatic Amine Aniline
3 examples Amphetamine Amphetamines Methamphetamine Phentermine Common physiological effect: Reduce fatigue and diminish hunger by raising glucose levels Prescribed to: Counter mild depression Reduce hyperactivity in children Suppress appetites
2 Amphetamine C 3 C 3 Methamphetamine C 3 2 C 3 3 C Phentermine found in Fen-Phen
Illegally used to: Reduce Fatigue Elevate moods mood enhancement ADDICITIVE: Concentrated in Brain and CS leads to sleeplessness, weight loss, & paranoia Why? ow does it work? Action similar to Epinepherine Excreted by adrenal gland Makes glucose more available Immediate glucose action Commonly called Adrenalin O O O C 3
eterocyclic Amines eterocyclic Aliphatic Amines pyrrolidine piperidine eterocyclic Aromatic Amines pyrrol pyridine
1. ow many hydrogens does piperidine have? 11 C 5 11 2. ow many hydrogens does pyridine have? 5 C 5 5 3. Write the molecular formula of each. 4. ow many hydrogens does pyrrolidene have? 9 C 4 9 5. ow many hydrogens does pyrole have? 5 C 4 5 6. Write the molecular formula of each.
Alkaloids aturally occurring amine compounds Found in roots, bark or fruits itrogen found in ring Alkaloid because compounds are BASIC Coniine Water emlock Causes weakness, labored respiration, paralysis and death icotine Tobacco plant Addictive in small doses Large doses cause depression, nausea, vomiting Cocaine Leaves of Coca plant CS stimulant
C 3 (s) Coniine C 3 (s) icotine O O O Cocaine O
Section 16.3 omenclature Same naming system as ALCOOLS Drop the ending or e of the parent chain and add amine 3 C 2 3 C 2 2 C 3 2 1,6-hexandiamine 2-propanamine 1-phenyl-1-ethanamine
Write the name or formula 1. C 3 (C 2 ) 5 2 1-hexanamine 2. 1-phenyl-2-propanamine 3 C 2 3. Cyclohexanamine 2 4. 1,4-butandiamine 2 2
IUPAC nomenclature retains the common 2 name: Aniline 2 2 3 C Toluidine is methyl substituted aniline 2-methyl aniline = o-toluidine Largest group bonded to nitrogen is the parent amine when nitrogen has 2 or more carbon groups bonded to it (IUPAC) Groups attached to itrogen are numbered as C 3
C 3 -methylaniline,-dimethyl cyclopentanamine 3 C C 3 -ethyl-2-propanamine 3 C C 3 -ethyl--methyl ethanamine C 3 C 3 3 C C 3
Common ames Common names for aliphatic amines list the groups bonded to the nitrogen in alphabetical C 3 C 3 C order. 2 C 2 3 C 2 Methylamine tert-butylamine diethylmethylamine Draw the structure of Cyclohexylmethylamine Isopropylamine Triethylamine C 3 C 3 2 C C 3 C 3
Amine Salts When 4 atoms or groups are bonded to the nitrogen amed as a salt with an anion (chloride) Ending amine is replaced with -ammonium_ Ending aniline is replaced with -anilinium Ending pyridine is replaced with -pyridinium
Ammonium chloride + Cl - Tetramethyl ammonium chloride C 3 Cl - C + 3 C 3 C 3 Pyridinum chloride + Cl - Anilinium chloride + Cl -
Section 16.4 Physical Properties Amines are POLAR molecules Primary and Secondary amines will form -Bonds between themselves Tertiary amines will OT form -Bonds between themselves ALL amines will form -Bonds with WATER! The - h-bond is WEAKER than the O- h- bond.
Methanamine vs. Methanol C 3 2 C 3 O Molar Mass 31.1 32.0 Boiling Point -6.3⁰C 65.0⁰C Why? Stronger -Bonding between Methanol Molecules
Section 16.5 Basicity Amines are _Slightly Strong to Weak Bases Example: C 3 + O 3 C + + O - Base dissociation constants K b [ C 3 ][ O ] 4 3 4.37x10 [ C ] 3 2
2 ways to measure base strength pk b -Log of K b Smaller values = Stronger Bases <3 = Very Strong base >6 = Weak Base p Larger values = Stronger Bases 13-14 = Very Strong base 8-10 = Weak Base
Amine pk B Base ature Aliphatic 3.0-4.0 Slightly Strong Ammonia 4.74 Aromatic 8.5-9.5 Weak
2 3 For each Set, choose which is the more basic 2 2 C 3 3 C
Basicity and Blood Most Aliphatic amines are fairly strong bases ow will they be found in the blood stream? In their Ionic or Ammonium Form Example: Dopamine O 2 O + O O
Section 16.6 REACTIOS O Amines react with strong acids to form watersoluble salts O 2 O O + + Cl + Cl - O O (R) orepinephrine Only Slightly water soluble (R) orepinephrine hydrochloride Very water soluble
Solubility of amine type DRUGS Many drugs have Cl in their chemical formula WY? igh molecular weight amines are insoluble in blood Treated with an acid they form a water/blood soluble salt Amines are also susceptible to oxidation from atmospheric O2. Amine salts are less likely to be oxidized and retain a longer shelf life LOOK AT LABELS!
Examples Phenylephrine Cl Is it (R) or (S)? (eo-synephrine) Procaine Cl (ovocain) O 2 O O O C 3 C 3 Cl C 3 Cl O Methadone Cl (Methadone) C 3 C 3 C 3 C 3 Cl Albuterol Cl (Proventil) O O O C 3 C3 C 3 Cl
Chapter 17: Aldehydes & Ketones aming Introduction Aldehydes Terminal CO group Suffix: al aming similar to alcohols Ketones Internal C=O group Suffix: one aming similar to alcohols O 3 C C 3 C C 3 C O
ame the Following C 3 O O 3 C C 3 C 3 C 3 3C C 3 C3 Cl C 3 O O
Draw the Following 1,6-dichloro-3-hexanone 5-methylheptanal 1,6-hexandial 3-bromo-2-butanone
Sections 17.1-17.3 Order of Precedence of Main Functional Groups Class Group Suffix if highest Prefix if Lower Carboxylic acid ighest -COO -oic acid ever Lower! Aldehyde -CO -al oxo Ketone -C=O -one oxo Alcohol -O -ol hydroxy Amine - 2 -amine amino
Examples: Draw the following 2-aminohexanal 1-amino-2-hydroxyl-3-pentanone 5-hydroxyl-2-hexenal 3-methyl-2-oxobutanal 4-amino-3-penten-2-one
ame the following O C 3 O C 2 3 C C 3 O O O O O C 3 O 2