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PHARMACEUTICAL SEMINAR 1 (PRELIMS) ORGANIC CHEMISTRY PART 1 Ms. Cristal B. Pedong, RPh | August 29, 2023 | CSI ORGANIC CHEMISTRY Branch of chemistry that...

PHARMACEUTICAL SEMINAR 1 (PRELIMS) ORGANIC CHEMISTRY PART 1 Ms. Cristal B. Pedong, RPh | August 29, 2023 | CSI ORGANIC CHEMISTRY Branch of chemistry that deals with carbon-containing compounds except carbonates, bicarbonates, cyanides and oxides. - Organic came from the term organism because during those times people believed that organic compounds are only isolated from living organisms or remains. ORGANIC COMPOUNDS INORGANIC COMPOUNDS Flammable Non-flammable Low melting point HIgh melting point Low boiling point High boiling point Soluble in nonpolar solvents Insoluble in nonpolar solvents Insoluble in water Soluble in water Covalent bonding Ionic bonding Many atoms Few atoms UREA UREA (CH4N2O) aka Carbamide “Wöhler synthesis” – heated inorganic compound ammonium cyanate produced urea ○ Friedrich Wohler - he demonstrated that a biomolecule such as urea can be synthesized from non-biological starting material. He prepared urea from ammonium cyanate ○ Vitalism - a theory, they believed that organic molecules cannot be produced from inorganic molecules Ways to produce urea: ○ Inorganic Process: Isomerization ○ Organic Process: By product of protein metabolism, from proteins we have amino acids particularly ornithine and it will go urea cycle to produce urea HISTORY In 1828, Friedrich Wohler, a German chemist, disproved the “Vitalism” theory which states that all organic compounds come from living things. He was able to isolate urea from an inorganic compound, ammonium cyanate. 1 | CSI  UNIQUENESS OF CARBON Carbon is able to form 4 covalent bonds (4 valence electrons) with other carbon or other elements. Carbon atoms have the ability to bond to each other to form long chains or rings. Ability to Catenate ○ Catenation - ability of atoms to form stable bonds with itself Carbon atoms link together to form chains of varying length, branched chains and rings of different sizes Atomic Structure Charge of atoms are usually neutral because the no. of positive protons in the nucleus and the no. of electrons outside the nucleus are the same Nucleus containing the protons and neutrons is responsible for the weight of the atom, while electron is usually weightless ELEMENTS Fundamental building blocks of all substances Atoms: Smallest particle of an element Neutron: Neutral subatomic particle Proton: Positively charged subatomic particle (+1 charge) Electron: Negatively charged subatomic particle (-1 charge) Nucleus: Center of an atom; contains protons and neutrons An atom consists of a nucleus surrounded by electrons that are equal in number to the protons of the nucleus ATOMIC NUMBER AND ATOMIC MASS The atomic number (Z) - number of protons in nucleus (superscript) The mass number (A) - number of protons plus neutrons (subscript) ISOTOPES Atoms of the same element with different numbers of neutrons and thus different mass number (A). Determine the number of protons, neutrons and electrons present in atoms of the following: 2 | CSI  ATOMIC STRUCTURE ORBITALS ORBITALS - region of space where there is a certain probability of finding an electron - Can hold 2 electrons - Also known as WAVE FUNCTION Four Different Kinds of Orbitals: s - spherical p - dumbbell d - four leaf clover f - complex DISTRIBUTION OF ORBITALS WITHIN SHELLS Each shell contains subshells known as atomic orbitals. Electrons are said to occupy orbitals in an atom. SUBSHELL NO. OF ORBITALS OF EQUAL MAXIMUM NUMBER OF ENERGY ELECTRONS s 1 2 p 3 6 d 5 10 f 7 14 SHELL ORBITALS CONTAINED MAXIMUM NO. OF RELATIVE ENERGIES IN EACH SHELL ELECTRONS SHELL OF ELECTRONS IN CAN HOLD EACH SHELL 4 one 4s 2 + 6 + 10 + 14 = 32 three 4p five 4d seven 4f orbitals 3 one 3s 2 + 6 + 10 = 18 three 3p five 3d orbitals 2 one 2s 2+6=8 three 2p orbitals 1 one 1s 2 3 | CSI Main Group Elements Inner-transition elements s-block: Group 1A and 2A f-block: 4f and 5f p-block: Group 3A to 8A Transition Elements d-block: Group 1B to 8B ELECTRON PRINCIPLES AUFBAU PRINCIPLE - states that electrons fill lower-energy atomic orbitals before filling higher-energy ones - Low energy levels are filled up first PAULI’S EXCLUSION PRINCIPLE - No 2 electrons can have the same set of 4 quantum numbers. Each atomic orbital can only accommodate 2 electrons HUND’S RULE - for degenerate orbitals, electrons fill the orbitals singly before they pair up HEISENBERG’S UNCERTAINTY PRINCIPLE - It is impossible to know simultaneously both the momentum and position of particle with certainty QUANTUM NUMBERS SYMBOL VALUES FUNCTION Principal QN n 1,2,3 Determine the size of the particle Azimuthal QN l 0 to (n-1) Subshell or sublevel, determines the shape Magnetic m -1 to +1 orbitals, determines orientation, involvement of magnetic field Spin s -1/2 to +1/2 direction of spin or orientation 4 | CSI  ELECTRON CONFIGURATION symbolic notation of the manner in which the electrons of its atoms are distributed over different atomic orbitals summary of where the electrons are around a nucleus Ex: 1s2 2s2 2p6…. as well as the box and arrow method For electron configuration, all you need to do is look for the number of electrons in an atom or element. How to determine the electrons? Look for the atomic number. Ex: Nitrogen has atomic number of 7 it means it also have 7 electrons RULES: 1. Lowest-energy orbitals fill first: 1s 🡪 2s 🡪 2p 🡪 3s 🡪 3p 🡪 4s 🡪 3d (Aufbau “build-up” principle) 2. Electrons act as if they were spinning around an axis. Electron spin can have only two orientations, up ↑ and down ↓. Only two electrons can occupy an orbital, and they must be of opposite spin (Pauli exclusion principle) to have unique wave equations. 3. If two or more empty orbitals of equal energy are available, electrons occupy each with spins parallel until all orbitals have one electron (Hund’s rule) Number of boxes per orbital (each orbital can only accommodate 2 electrons): s-orbital: 1 box p-orbital: 3 boxes Take Note: for each orbital upward spin must be fill first POP QUIZ: Write ground-state electron configurations for these elements. A. Oxygen B. Magnesium C. Chlorine D. Potassium 5 | CSI  E. Silicon CHEMICAL BONDING OCTET RULE - atoms react in a way that achieve valence shell of eight valence electrons. IONIC BOND - bond between anion and cation - atom may lose or gain enough electrons to acquire a completely filled valence shell - anions (-) gain electrons; cations (+) lose electrons CHEMICAL BONDING joining of two atoms in a stable arrangement may occur between atoms of the same or different elements. favorable process because it always leads to lowered energy and increased stability Atoms form bonds because the resulting compound is more stable than the separate atoms Ionic bonds in salts form by electron transfers Organic compounds have covalent bonds from sharing electrons FORMATION OF IONS Octet Rule – The tendency among atoms of group 1A-7A elements to react in ways that achieve an outer shell of eight valence electrons. Anion – an atom or group of atoms bearing a negative charge. Cation – an atom or group of atoms bearing a positive charge. COVALENT BONDING LEWIS STRUCTURE - Electron dot structure - Valence shell electrons of an atom are represented as dot KEKULE STRUCTURE - Line bond structure - Each shared electron is represented by line between the atom symbols LEWIS STRUCTURE H has one bond C has four bonds N has three bonds and one unshared pair of electrons 6 | CSI  O has two bonds and two unshared pair of electrons F, Cl, Br, and 1 have one bond and three unshared pairs of electrons. LONE-PAIR ELECTRONS - or non-bonding electrons - Pair of valence electrons that are not used for bonding POP QUIZ: Draw Lewis structures, showing all valence electrons, for these molecules: A. H2O2 B. CH3OH C. CH3Cl MULTIPLE BOND When 2 atoms share more than 1 pair of electron Double Bond Triple Bond C2H4 - Ethylene C2H2 - Acetylene or Ethyne 7 | CSI Alkanes - aka paraffin - CnH2n + 2 - single bond C-C - suffix - ane and -yl (alkyl) - Alkyl groups are alkane with one hydrogen atom removed. - Van de waals - oxidation Alkenes Alkynes - aka olefin - aka acetylene - CnH2n - CnH2n - 2 - double bonds C=C - triple bonds - Suffix -ene - Van der waals, hydrophobic - Hydration, epoxidation, peroxidation, reduction IDENTIFYING FORMAL CHARGES Formal Charge Associated with any atom that does not exhibit the appropriate number of valence electrons. Charge assigned to an atom in a molecule ○ 1st: Determine the number of valence electrons Valence electron - also refer to group number (horizontal part) ○ 2nd: Determine whether the atom exhibits appropriate number of electrons ○ FC = [# valence e-] – [non-bonded e- + number of bonds] ELECTRONEGATIVITY AND BOND POLARITY ELECTRONEGATIVITY - Measure of the ability of an atom to attract electrons - Fluorine is the most electronegative element 8 | CSI Electronegativity increases from left to right and from bottom to top POP QUIZ Based on the relative positions in the periodic table, which element in each pair has the larger electronegativity? A. Lithium or Carbon - Ans: Carbon B. Carbon or Oxygen - Ans: Oxygen C. Nitrogen or Oxygen - Ans: Oxygen INDUCTION AND POLAR COVALENT BONDS Difference in electronegativity < 0.5 - Non-polar covalent bond - Equally shared electrons between the 2 atoms Difference in electronegativity 0.5-1.7 - polar covalent bond - not equally shared electrons between atoms INDUCTION - withdrawal of electrons towards a highly electronegative atom which causes the formation of partial charges - The more electronegative the compound the more it will be able to attract electrons from other element Difference in electronegativity >1.7 - ionic bond - electrons are not shared - NaOH DRAWING CHEMICAL STRUCTURES Shorthand ways of writing structures Condensed Structures: C-H and C-C and single bonds aren’t shown but understood - If C has 3 H’s bonded to it, write CH3 - If C has 2 H’s bonded to it, write CH2 and so on. Sometimes bonds between carbons aren’t shown in condensed structures-here the CH3+, CH2+, and CH units are drawn next to one another, but some bonds are added for clarity. The compound called 2-methylbutane, for example, is written as follows: 9 | CSI  EXPANDED CONDENSED SKELETAL Propane 2-methyl-2-pentene 2-methyl-1-propanol Octane PHYSICAL PROPERTY A property that does not affect the chemical identity of a compound Can be observed and measured without changing a compound’s composition of matter ○ Any substance that has mass and can occupy space INTERMOLECULAR FORCES The physical properties of molecules are in part dependent on the type of intermolecular forces (IMF) present. Boiling points (BP) are also dependent on the mass of the molecule. Solubility, the ability to dissolve into a solvent is dependent on IMFs. The strength of the interaction between molecules is also dependent on the overall shape of the molecule. There are 3 types of IMFs, by decreasing strength they are: ○ Hydrogen bonding ○ Dipole-dipole ○ Van der Waals or London Dispersion 10 | CSI  HYDROGEN BONDING Hydrogen bonding is a complex interaction that includes dipole-dipole, as well as orbital interactions and the transfer of electron density between molecules. These are the strongest of the IMFs and range from 5 – 25 kJ/mol Occur primarily between OH, NH and FH. The more EN the atom the stronger the interaction. (The atom H is attached to usually has a lone pair of e- ) This is the reason why it takes a longer minute to boil water DIPOLE-DIPOLE Dipole-dipole forces arise from the attraction of oppositely charged atoms (other than H) in molecules. These molecules may have a permanent dipole moment. Generally in organic molecules they result from the presence of C-X bonds where X is more electronegative than C. These are generally weaker than H-bonding, ranging from about 5-10 kJ/mol. Dipole Moment - occurs when there is a separation of charge, it also occurs between two ions in an ionic bond or even between atoms in a covalent bond. It also arises from the difference in electronegativity. - The larger the difference in electronegativity, the larger the dipole moment - It also measures the polarity of a molecule VAN DER WAALS Van der Waals or (London) dispersion forces arise from the movement of electrons within a molecule. This natural motion can produce an uneven distribution of the electrons (polarization of the distribution) resulting in a temporary dipole moment in the molecule. This will induce the movement of electrons in adjacent molecules producing a dipole moment in them. These “induced” dipole moments are very brief as they disappear when the electrons move to new locations within the molecule, so they forces are very brief and weak, only 2-5 kJ/mol. It is weak because it is dependent on the distance of atoms within a molecule. Van der waals is weaker than covalent and ionic bonds a. London/Dispersion Forces - weakest aka induced dipole - induced dipole (2 nonpolar) b. Keesom Forces - interaction between the dipoles in polar molecules. aka dipole - dipole (2 polar) c. Debye Forces - aka dipole - induced dipole, forces that are cause by interaction of permanent dipole and other atoms or molecules which result to formation of induced - dipole (polar and nonpolar) Polar - Dipole Nonpolar - Induced Dipole STRUCTURAL EFFECTS ON IMFs The strength of the IMFs depends on the amount of contact between the molecules, especially for dispersion forces. Hence the shape of the molecule can affect the surface area of contact, long thin molecules have more surface in contact than spherical molecules. 11 | CSI  FACTORS AFFECTING THE PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS Structure of Functional Group Molecules having a polar functional group have a higher b.p. than others with a non-polar functional group of similar molecular masses. Water is the most polar solvent or organic molecule LENGTH OF CARBON CHAINS Molecules with higher molecular masses have higher m.p., b.p. and density ○ Higher molecular masses ○ Large molecular sizes ○ Stronger London dispersion forces among molecules Molecules with branched chains ○ b.p. and density lower than its straight-chain isomer Straight-chain isomers have greater surface area in contact with each other ○ Greater attractive force among the molecules As a rule, larger molecules have higher boiling (and melting) points. ○ Methane BP: -164 C, Butane BP: 0 C, Hexane BP: 68 C, Octane BP: 128 C SOLUBILITY If the solvent is polar, like water, then a smaller hydrocarbon component and/or more charged, hydrogen bonding, and other polar groups will tend to increase the solubility. Like dissolves like The number of Carbons. More carbons means more of a non-polar/hydrophobic character, and thus lower solubility in water. Anything with a charged group (eg. ammonium, carboxylate, phosphate) is almost certainly water soluble, unless it has large nonpolar group, in which case it will most likely be soluble in the form of micelles, like a soap or detergent. Any functional group that can donate a hydrogen bond to water (eg. alcohols, amines) will significantly contribute to water solubility. Any functional group that can only accept a hydrogen bond from water (eg. ketones, aldehydes, ethers) will have a somewhat smaller but still significant effect on water solubility. Other groups that contribute to polarity (eg. alkyl halides, thiols sulfides) will make a small contribution to water solubility. BOILING POINT AND MELTING POINT 12 | CSI  Melting and boiling are processes in which noncovalent interactions between identical molecules in a pure sample are disrupted. The stronger the noncovalent interactions, the more energy that is required, in the form of heat, to break them apart. CHEMICAL PROPERTIES A chemical reaction occurs when one substance is converted into another substance(s). A chemical reaction is accompanied by breaking of some bonds and by making of some others. REACTION MECHANISM Define as the detailed knowledge of the steps involved in a process in which the reactant molecules change into products. Chemical reactions involve breaking of one or more of the existing chemical bonds in reactant molecule(s) and formation of new bonds leading to products. The breaking of a covalent bond is known as bond fission. During bond breaking or bond fission, the two shared electrons can be distributed equally or unequally between the two bonded atoms. Fission - the action of dividing or splitting something into two parts HOMOLYTIC FISSION The fission of a covalent bond with equal sharing of bonding electrons. Free radicals are neutral but reactive species having an unpaired electron and these can also initiate a chemical reaction. Result of homolytic fission HETEROLYTIC FISSION The fission of a covalent bond involving unequal sharing of bonding electrons. This type of bond fission results in the formation of ions. The ion which has a positive charge on the carbon atom, is known as the carbonium ion or a carbocation. On the other hand, an ion with a negative charge on the carbon atom is known as the carbanion. ○ Ions - result of heterolytic fission The charged species obtained by the heterolytic fission initiate chemical reactions and they are classified as electrophiles and nucleophiles. Electrophiles: An electrophile is an electron deficient species and it may be positively charged or neutral. Examples are H+ , AlCl3 , Br2 , Cl2 , Ag+ , CH3 +, BF3 etc. ○ Love electrons, negative charge loving, accept electrons Nucleophiles : A nucleophile is negatively charged or electron rich neutral species. Examples of nucleophiles are OH– , –NO2+ , H2O, :NH3 etc. ○ Seeks a positive center / nucleus loving, provide electrons TYPES OF REACTIONS IN ORGANIC COMPOUNDS SUBSTITUTION A substitution reaction involves the displacement of one atom or group in a molecule by another atom or group. Aliphatic compounds undergo nucleophilic substitution reactions. 13 | CSI  ○ Aliphatic Compounds - containing carbon and hydrogen joined together using straight chain or branched chain or non-aromatic rings. For example, a haloalkane can be converted to a wide variety of compounds by replacing halogen atom (X) with different nucleophiles as shown below. Another type of substitution reaction which takes place in aromatic hydrocarbons. In this case, an electrophilic reagent attacks the aromatic ring because the latter is electron rich. The leaving group, in this case, is always one of the hydrogen atom of the ring. ELIMINATION An elimination reaction is characterized by the removal of a small molecule from adjacent carbon atoms and the formation of a double bond. ADDITION Unsaturated hydrocarbons such as alkenes and alkynes are extremely reactive towards a wide variety of reagents. The carbon-carbon double bond (–C=C–) of an alkene contains two types of bonds. In alkynes, three carbon-carbon bonds. Ex: carbonyl (C=O), imine (C=N) MOLECULAR REARRANGEMENTS proceeds with a fundamental change in the hydrocarbon skeleton of the molecule. During this reaction, an atom or group migrates from one position to another. 14 | CSI  PHARMACEUTICAL SEMINAR 1 (PRELIMS) ORGANIC CHEMISTRY PART 2 ISOMERS These are compounds with the same molecular formula and same molecular weight but different structural formula, this differ in physical and chemical properties. Isomerism - is the phenomenon in which more than one compound have the same chemical formula but different chemical structure. STRUCTURAL ISOMERS aka Constitutional Isomerism Compounds with same molecular formula but different in structure CHAIN ISOMERS aka Skeletal Isomerism Same molecular formula, but different arrangements of the carbon ‘skeleton’. The positions of the carbon atoms can be rearranged to give ‘branched’ carbon chains coming off the main chain. Alteration the way the carbons are joined, changes in the parent chain The name of the molecule changes to reflect this, but the molecular formula is still the same. 15 | CSI  POSITIONAL ISOMERS Same molecule formula; same functional group, but its position in the molecule changes. ○ Changes of position of double bonds or functional groups The name of the molecule changes to reflect the new position of the functional group FUNCTIONAL ISOMERS Same molecular formula but the atoms are rearranged to give a different functional group. The name of the molecule changes to reflect the new functional group. Ex: alcohol → ether, COOH → esters, ketones → aldehydes CONSTITUTIONAL ISOMERS Same atoms but linked together differently Same molecular formula different connectivity STEREOISOMERISM Arises in compounds having the same formula but different orientation of the atoms belonging to the molecule in a 3 dimensional space Positioning the different functional groups in their sites of action Three main groups: 1. Optical Isomer - Mirror images - ENANTIOMER – D and L forms - DIASTEREOMER ex. Epimers 2. Geometric Isomers - Changes in position of the constituents - Cis and Trans 16 | CSI  3. Conformational Isomers - Usually use in sugars - Boat and Chair OPTICAL ISOMERS - Compounds that exhibit optical isomerism feature similar bonds but different spatial arrangement of atoms forming non-superimposable mirror images. - contain at least one asymmetric, or chiral, carbon atom - Chiral - carbons that have four non-identical substituents around it (aka chiral center or stereogenic center or stereo centers) - Any chiral carbon will exhibit isomerism - Each attachment must be different - The presence of double bond indicate non-chiral Each asymmetric carbon atom can exist in one of two non-superimposable isomeric forms POP QUIZ: Chiral or Non-chiral Chiral two carbons at the middle are considered chiral 17 | CSI Carbon no. 2 and 4 are chiral ENANTIOMERS AND DIASTEREOMERS Enantiomers are mirror images of each other and non superimposable, Diastereomers are not mirror images of each other and non-superimposable How to identify the dextro and levo? - Look for the ultimate or last carbon attachment of OH, it will depend on the configuration of the highest number chiral carbon atom. In short, just look for the bottom most carbon, if the OH is in the right side it is considered dextro and if it's in the left side it is levo - For amino acids check for the position of NH2 EPIMERS Isomers differing as a result of variations in configuration of the —OH and —H on carbon atoms 2, 3, and 4 of glucose are known as epimers Epimers are examples of diastereomers that differ from each other in the configuration at only one chiral carbon. Ex: Mannose and Galactose which are diastereomers of glucose Glucose and Mannose: C2 epimer Glucose and Galactose: C4 epimer GEOMETRIC ISOMERS Commonly exhibited by alkenes, the presence of two different substituents on both carbon atoms at either end of the double bond Two different non superimposable isomers due to the restricted rotation of the bond. Requirement for Geometric Isomerism - It must have double bond - Carbon double bond carbon must be attached to two different groups Cis (latin) / Zusammen (german) - same or same location (sister always together) - Z → cis = same side Trans (latin) / Entgegen (german) - opposite side (transferred away) - E → trans = opposite side OPTICAL ISOMERS Differ by the placement of different substituents around one or more atoms in a molecule. 18 | CSI  Different arrangements of these substituents can be impossible to superimpose Differ by the placement of different substituents around one or more atoms in a molecule. Different arrangements of these substituents can be impossible to superimpose. Positive sign (+) dextrorotatory / Negative sign (-) levorotatory If the substance is optically active it can rotate polarimeter S,R - based on absolute configuration R (rectus) - clockwise S (sinister) - counterclockwise Dextro and Levo - based on the optical activity Take Note: Dextro/Levo and S/R enantiomers have no direct correlation Racemic Mixtures - containing equal amounts of dextro and levo. These are optically inactive IMPORTANCE OF ISOMERISM (S) - ibuprofen - Capable of inhibiting the COX (R) - ibuprofen - Not considered as COX inhibitor (S) - thalidomide - Teratogenic (R) - thalidomide - Sedative for morning sickness - The current use of thalidomide nowadays is for leprosy treatment BIOISOSTERES groups that are spatially and electronically equivalent and, thus, interchangeable without significantly altering the molecules’ physicochemical properties. Swapping of groups that preserve the same charges and hydrogen bonding activity PURPOSE EXAMPLES Enhance desired biological or physical Fluorine vs Hydrogen properties Hydroxyl vs Amino Acids Increased potency Hydroxyl vs Thiol Groups Decreased side-effects Methyl, Methoxyl, Hydroxyl, Amino groups Increase duration of action vs Hydrogen Fluoro, Chloro, & Bromo, thiol, vs Methyl & other small alkyl groups POP QUIZ 19 | CSI  HYDROCARBONS Chemical compounds composed only of hydrogen and carbon atoms ALIPHATIC HYDROCARBONS hydrocarbon compounds joined together in straight chains, branched chains or non-aromatic rings ALKANES ALKENES ALKYNES CYCLIC paraffins olefins acetylenes prefix – cyclo sp3 hybrid sp2 hybrid sp hybrid suffix – ane suffix – ene suffix – yne AROMATIC HYDROCARBONS carbocyclic compounds containing conjugated double bonds Benzene – simplest aromatic hydrocarbon August Kekule (1865) Kathleen Lonsdale (1929) Benzene ring as a flat molecule, having Used X-ray crystallography to show alternating single and double bonds between carbon-carbon bonds in a benzene ring are the carbon atoms same length 20 | CSI  HYDROCARBONS DERIVATIVES One or more hydrogen atoms in the molecules is replaced by certain group of atoms Carbonyl: C=O ALCOHOLS With hydroxyl (-OH) functional group R-OH 21 | CSI  Prefix – hydroxy Suffix – ol EXAMPLES OTHER NAME STRUCTURES Methanol Wood Alcohol Ethanol Grain Alcohol Phenol Carbolic Acid PHENOLS With hydroxyl (-OH) functional group attached to a carbon atom that is a part of an aromatic ring, Ar-OH ETHERS Alkoxy-substituted alkanes R-O-R Formed by the bimolecular dehydration of alcohols with sulfuric acid ALDEHYDES Contains at least 1 hydrogen atom attached to the carbonyl carbon. Functional Group is at terminal RC=OH 22 | CSI  Formed by oxidation of primary alcohols Prefix – oxo Suffix – al EXAMPLES OTHER NAME STRUCTURES Methanal Formaldehyde Ethanal Acetaldehyde CH3CHO Propanal Propionaldehyde CH3CH2CHO KETONES Contains two carbon groups bonded to the carbonyl carbon RC=OR Formed by oxidation of secondary alcohols Prefix – oxo Suffix – one EXAMPLES OTHER NAME STRUCTURES Propanone Acetone 2-butanone Ethyl methyl ketone 3-pentanone Diethylketone CARBOXYLIC ACIDS Produced by oxidation of aldehydes Contains the carboxyl functional group RC=OOH Suffix – oic acid 23 | CSI  AMIDES Formed by the reactions of organic acids with ammonia or with amides RC=ONH2 Suffix – amide CLASSIFICATION STRUCTURES Primary Amide Secondary Amide Tertiary Amide ESTERS Formed by the reactions of acids and alcohols with acid catalysts Alkyl alkanoate, RC=OOR Suffix – oate Acid catalyst usually used in the lab is sulfuric acid EXAMPLES OTHER NAME STRUCTURES Methyl methanoate Formate Reac: Methanol + Methanoic acid Methyl ethanoate Acetate Reac: Methanol + Ethanoic acid Ethyl methanoate Ethyl formate Reac: Ethanol + Methanoic acid AMINES Organic compound derived from ammonia RNH2 Prefix – amino Suffix – amine CLASSIFICATION STRUCTURES Primary Amine Ex: Methylamine (CH3NH2) Aniline (C6H5NH2) 24 | CSI  Secondary Amine Ex: Dimethylamine (CH3)2NH Diphenylamine (C6H5)2NH Tertiary Amine Ex: Trimethylamine N(CH3) EDTA NITRILES Organic compound derived from ammonia Cyanides, RCN Prefix – cyano Suffix – nitrile EXAMPLES STRUCTURES Ethanenitrile / Acetonitrile Propanenitrile ALKYL HALIDES Derivatives of alkanes in which one hydrogen in an alkane is replaced by a halogen RX, X = Cl, Br, I, F0 CLASSIFICATION STRUCTURES Primary Secondary Tertiary 25 | CSI