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23 • Organic Chemistry Historical Ideas (1 of 16) 23 • Organic Chemicals from living things were thought to contain a “vital force” that could not be duplicated in the lab. This changed with Friedrich Wöhler who mixed cyanic acid (HCNO) with ammonium hydroxide making ammonium cyanate (NH4CNO). 23 • Organic Chemistry O He usually allowed the salt solution to Historical Ideas C evaporate overnight, but tried heating it to NH (1 of 16) H2N 2 hurry the process. The result was a crystal urea that he recognized as urea (H2NCONH2). The modern view of organic chemistry is the chemistry of carbon compounds. C is the key element. It can form four bonds and that are very strong bonds due to its small size. The alkanes (paraffins) follow the formula: CnH2n+2: These molecules contain ONLY single bonds. They are said to be “saturated” with hydrogens. 23 • Organic Chemistry Memorize these prefixes also used with alkenes & alkynes. CH4 methane C6H14 hexane Alkane Series -- Saturated Hydrocarbons C2H6 ethane C7H16 heptane (2 of 16) C3H8 propane C8H18 octane C4H10 butane C9H20 nonane C5H12 pentane C10H22 decane Given a formula, you can tell that it contains only single bonds because it fits the alkane formula. As the molecules increase in size, they tend to be liquids and H CH4, can be drawn using a structural formula. This can be misleading. The molecule is not flat H C H with bond angles of 90°. You must be aware of H the 3-D structure and the 109.5° bond angles. 23 • Organic Chemistry Structural Formulas Can Be Misleading Cl Cl For example, there is only one isomer (3 of 16) H C H H C Cl of dichloromethane, but you can Cl H draw it at least two ways. Building models of the molecules is an important part of strengthening this skill. H H Alkenes contain 1 double bond. The formula is CnH2n. They are said to be “unsaturated” C C (like unsaturated fats). The double bond can H H be broken and more hydrogens added. ethene 23 • Organic Chemistry Since double bonds cannot easily rotate (due to the pi Alkenes and cis- /trans- Isomerism bonding) cis- and trans- isomers can be formed. (4 of 16) Example: 1,2-dichloroethene can be built two ways. Cl Cl Cl H C C C C H H H Cl cis -1,2-dichloroethene trans-1,2-dichloroethene (a polar molecule) (a nonpolar molecule) Alkynes contain 1 triple bond H C C H (unsaturated). Formula: C H . ethyne (acetylene) n 2n-2 The triple bond is linear, so no cis/trans isomerism occurs. Alkadienes are molecules with two double bonds. They 23 • Organic Chemistry have the same formula as the alkynes, CnH2n-2. H Alkynes, Alkadienes, and Cyclic Hydrocarbons Example: C4H6 is named 1,3-butadiene (5 of 16) because the double bonds start on C CH2 H C C carbons #1 and #3. 2 H H 2 Cyclic compounds contain rings having the C CH same formula as the alkenes, CnH2n. H C 2 2 Example: cyclopropane, C3H6. The basic idea is to name the molecule after the longest continuous chain of carbon atoms. Side groups are listed with #’s to indicate the C atom to which they are attached. Side Groups : -Cl chloro -Br bromo -I iodo 23 • Organic Chemistry -CH3 methyl -C2H5 ethyl -C3H7 propyl, etc. Naming Organic Compounds di - = 2 groups tri- = 3 groups tetra- = 4 groups (Organic Nomenclature Using IUPAC Rules) (6 of 16) 2,2,3-tribromobutane (not 2,3,3-) H Br Br H Note that we # the carbons from H C C C C H whichever end results in the H H Br H smallest numbers. While drawing the isomers of H H H pentane, C H , students draw this 5 12 H C C C H structure, naming it 2-ethylpropane. H CH H (a chain of 3 C’s with an ethyl group) 2 23 • Organic Chemistry The longest chain is four C’s, and CH3 Common Errors in Drawing/Naming Structures should be named 2-methylbutane. A similar error is to draw and name “1-methylsomething”. 1-methylsomething & 2-ethylsomething (7 of 16) H H Two more tips … double check that H C C O each C has four and only four bonds. Also, remember that N and O atoms H H have lone pairs of e-‘s although they 5 bonds to C are seldom drawn. (Impt. for steric #!) CH3 Some molecules have the ability to H C H 2 rotate polarized light. 2 C CH H 2 These molecules can be recognized H C C 3 by a C atom (the chiral carbon) 23 • Organic Chemistry CH3 bonded to four different groups . Optical Isomers 3-methylhexane Chiral Compounds This carbon is bonded to H, methyl, ethyl, & propyl groups. (8 of 16) You can build two versions of this molecule that are “nonsuperimposable mirror images of each other.” One will rotate light clockwise, one counterclockwise. In biology, these are called dextro- and levo- (D and L) forms. ethene is also called ethylene propene is also called propylene H C 3 2-methylbutane is also called isopentane. H 23 • Organic Chemistry HC 2 “Iso-“ means the same… the same two C methyl groups come branch from C #2. H3C Common Names You Should Know About CH 2-methylpentane is isohexane, etc. 3 (9 of 16) CH3 2,2-dimethylpropane is called neopentane. H C C CH These common names show up 3 3 occasionally in names… such as in CH 3 isopropyl alcohol. H H C C Benzene, C6H6, is unique. It HC CH HC CH can be drawn as shown, but HC CH HC CH the actual structure involves C C 2 H H a circular pi bond (sp 23 • Organic Chemistry two resonance structures orbitals & delocalized e-‘s). Aromatic Compounds Benzene is also shown with a circle as the pi bond. Benzene and its Derivatives The carbon #’s can be used for substituted 1 (10 of 16) benzene. Example: dichlorobenzene 6 2 1,2- is known as the ortho- position 1,3- is known as the meta- position 5 3 1,4- is known as the para- position 4 Paradichlorobenzene: the main ingredient in some moth balls. Alcohols General formula: R-O-H [R » Rest of molecule] 1 C atoms are classified as primary (1), C secondary (2), or tertiary (3) by the C C 1 number of C atoms it is bonded to. 3 23 • Organic Chemistry 1 C C A primary alcohol has the -OH group 2 Functional Groups I bonded to a primary carbon, etc. Alcohols and Ethers This is not a base because the -OH is covalent, not ionic. Naming: group + “alcohol” (e.g. ethyl alcohol or ethanol) (11 of 16) Ethers General formula: R-O-R’ [R’ can = R, but not H] Naming: two groups + “ether” H2 H2 diethyl ether was the 1st effective C C H C O CH surgical and dental anesthetic. 3 3 Aldehydes Ketones General formula: O O C C R R' R H 23 • Organic Chemistry Naming: names end in “al” names end in Functional Groups II or “aldehyde” “one” Aldehydes and Ketones methanaldehyde propanone (formaldehyde) (acetone) (12 of 16) Aldehydes and ketones both have a C=O group (carbonyl group). Aldehydes have it on an end carbon. Ketones have it on a middle carbon. Reactions: Primary alcohols can be oxidized into aldehydes. Secondary alcohols into ketones. Carboxylic Acids Esters General formula: O O C C R OH R OR 23 • Organic Chemistry Naming: names end - “oic names end - “ate” Functional Groups III acid” ethyl acetate Carboxylic Acids and Esters ethanoic acid (acetic acid + (acetic acid) ethyl alcohol) (13 of 16) Reactions: Acids can be made by oxidizing aldehydes. Esters are formed (“esterification”) from a carboxylic acid & an alcohol. Water is removed (a “condensation” reaction). Esters often have pleasant, agreeable odors (e.g. banana.) Amines Amides General formula: H H O N C R R NH 2 23 • Organic Chemistry Naming: names contain names end in Functional Groups IV “amino” or end in “amide” Amines & Amides “amine” acetamide (14 of 16) aminomethane (methylamine) The N may have 1 or 2 or all 3 H atoms replaced with groups. The lone pair on the N atom makes these molecules basic. Your body needs certain amines “vital amines” » “vitamins.” Monomer = one part Polymer = many parts H H One kind of polymer is made up of C C monomers that contain a double bond. The double bond can break and we can H H 23 • Organic Chemistry “ethylene” ADD to it… “Addition polymerization.” Polymers I H H H H H H H H Monomers & Addition Polymerization * C C * + C C ® * C C C C * (15 of 16) H H H H H H H H Different monomers form different polymers. This polymer would be called polyethylene. Replace on H on the monomer with Cl and you can make polyvinyl chloride, “PVC.” Another polymerization involves condensation reactions. O O H H HO OH C R C C C R OH H H 23 • Organic Chemistry HO a di-acid a di-alcohol (a glycol) Polymers II Esters form from an acid and an alcohol. Using a di -acid and Copolymers & Condensation Polymerization a di -alcohol, you can make a continuous chain by removing (16 of 16) water molecules. The resulting polymer is called a polyester. Soda bottles are made from a polyester, polyethylene terephthalate ester (PETE). Nylon (a polyamide) can be made from a di-amine & a di-acid. .
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