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Examples of Organic Molecule Projects. Honors Chemistry Spring 2009. Dichlorophenoxyacetic Acid ( Proper). By Jon Ericksen and Kathryn Marbury. Dichlorophenoxyacetic acid is known as many more commonly used names, such as:. *2,4-D * Weedtrine -II *Aqua- Kleen *Barrage
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Examples of Organic Molecule Projects Honors Chemistry Spring 2009
Dichlorophenoxyacetic Acid (Proper) By Jon Ericksen and Kathryn Marbury
Dichlorophenoxyacetic acid is known as many more commonly used names, such as: *2,4-D *Weedtrine-II *Aqua-Kleen *Barrage *Plantgard *Lawn-Keep *Planotox *Malerbane.
Empirical and Molecular Formula C8H6Cl2O3
Molar Mass of C8H6Cl2O3 C x 8= 96.08 H x 6= 6.06 Cl x 2= 70.90 = 221.04 g/mol O x 3= 48.00
H H Halide O Ether H C C O C Cl C C C OH H C C H Cl Ethyl Group Alcohol CycloHexyl Group Halide Polar Bond Structural Formula Nonpolar Bond
O O Cl OH Cl Skeletal Formula
Space-Filling Formula Carbon Oxygen Chlorine Hydrogen
2,4-D’s Uses • 2,4-D is used and sold in many different forms in a wide variety of brand-name products and is used in over 1,500 herbicide products. 2,4-D is most commonly used for: • Weed control in lawns and other turf • No-till burndown • Control of weeds and brush along fences and highway and railroad rights of way • Conifer release (control of broad-leaf trees in conifer plantings) • Grass hayfields and pastures • Cereal grains • Corn and sorghum (occasionally) • As a synthetic auxin analogue
How It’s Made 2,4-D is commonly prepared by the condensation of 2,4-dichlorophenol with monochloroacetic acid in a strongly alkaline medium at moderate temperatures (Canada, NRC, 1978; Sittig 1980; QueHee & Sutherland, 1981), or by the chlorination of phenoxyacetic acid, but this method leads to a product with a high content of 2,4-dichlorophenol and other impurities (Melnikov, l97l). Higher reaction temperatures and alkaline conditions during the manufacture of 2,4-D increase the formation of polychlorinated dibenzo- p-dioxin (CDD) by-products (Fig. 2). The alkali metal salts of 2,4-D are produced by the reaction of 2,4-D with the appropriate metal base.
How It’s Made Cont’d Amine salts are obtained by reacting stoichiometric quantities of amine and 2,4-D in a compatible solvent (QueHee & Sutherland, 1974, 1981). Esters are formed by acid-catalysedesterification with azeotropic distillation of water (QueHee & Sutherland, 1981) or by a direct synthesis in which the appropriate ester of monochloroacetic acid is reacted with dichlorophenol to form the 2,4-D ester (Canada, NRC, 1978).
History 2,4-D was developed during World War II by a British team, aiming to increase crop yields for a nation at war. When it was commercially released in1946, it became the first successful selective herbicide and allowed for greatly enhanced weed control in wheat, maize (corn), rice, and similar cereal grass crops, because it only kills dicots, leaving behind monocots. 2,4-D is the third most commonly used herbicide in North America and the most widely used herbicide in the world.
ASCORBIC ACID CAITLIN ACAP PATRICK WALKER
PROPER L-3-Ketothreohexuronic acid lactone 3-keto-L-gulofuranolactone 3-oxo-L-gulofuranolactone L-threo-hex-2-enonic acid, gamma lactone COMMON Vitamin C L-ascorbic acid L-xyloascorbic acid Antiscorbutic vitamin Antiscorbic vitamin NAMES
EMPIRICAL FORMULA C3H4O3
MOLECULAR FORMULA C6H8O6
MOLAR MASS • C6= 12.011 x 6 = 72.066 • H8= 1.008 x 8 = 8.064 • O6= 15.999 x 6 = 95.994 72.066 8.064 95.994 176.124 g/mol
STRUCTURAL FORMULA • Functional Group: Ester • Hexyl Carbon Group • Alcohol (4) • Alkene
ASCORBIC ACID • KEY: • (HOMEMADE MODEL) • Carbon=Blue • Hydrogen=Red • Oxygen= Green • KEY: • (INTERNET MODEL) • Carbon=Blue • Hydrogen-White • Oxygen=Red • Oxygen and Hydrogen: Polar Covalent Bond • Carbon and Hydrogen: Nonpolar Covalent bond • Carbon and Carbon: Nonpolar Covalent Bond • Carbon and Oxygen: Polar Covalent Bond
Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Ascorbic acid is easily oxidized and is used as a reductant in photographic developer solutions (among others) and as a preservative. A vitamin used in preventing scurvy, as a strong reducing agent and as an antioxidant. Ascorbic acid is added to many foods for its nutritive value, but is also used to prevent flavors and colors from being damaged by oxidation. It is often used in canned or frozen fruits to prevent the browning that accompanies oxidation. Ascorbic acid prevents damage from oxygen free radicals. Other uses: Assists delayed wound and bone healing, chronic disease (Asthma, Pre-eclampsia, Age-related Macular Degeneration, Osteoarthritis, Cancer, the Common Cold, High Blood Pressure, Heart Disease) and urine acidification. WHAT ARE THE USES FOR ASCORBIC ACID?
HOW IS ASCORBIC ACID MADE? • Steps 1 thru 9 (Starch Hydrolysis): Corn starch is broken down into simple sugar (D-Glucose) by the action of heat and enzymes. Step 10 (Hydrogenation): D-Glucose is converted into D-Sorbitol. Step 11 (Fermentation): D-Sorbitol is converted into L-Sorbose. Step 12 (Acetonation): L-Sorbose is combined with an acid at low temperatures. Step 13 (Oxidation): The product is then oxidized with a catalyst, acidified, washed and dried forming L-Gluconic Acid. Step 14 (Hydrolysis): L-Gluconic Acid is treated with hydrochloric acid forming crude ascorbic acid. Step 15 (Recrystallization): The crude ascorbic acid is filtered, purified and milled into a fine crystalline powder.
Benzoic Acid By Sonia Ajmera and Alli Dillard
Common Name Benzoic Acid
IUPAC (International Union of Pure and Applied Chemistry) Nomenclature Benzoic Acid or Benzene Carboxylic Acid
Benzoic Acid • Benzoic Acid was discovered in the 16th century. • Benzoic Acid consists of a carboxyl group attached to a phenyl group, and is thus the simplest aromatic carboxylic acid. • It is also known as carboxybenzene, benzene carboxylic acid, and phenylformic acid.
Empirical and Molecular Formulas C₇H₆0₂ C₆H₅COOH
Molar Mass 122.12 g/mol C₇= 12.01115 x 7= 84.07805 84.07805 H₆= 1.0079 x 6= 6.0474 6.0474 O₂= 15.9994 x 2= 31.9988 +31.9988 122.12425 ≈122.12
Structural Formula Carboxylic Acid (Functional Group) O C C C C O H C C C Phenyl carbon group Carbon-Carbon: Non-polar covalent bond Carbon-Oxygen: Polar Covalent Carbon-Hydrogen: Non-polar covalent bond Oxygen-Hydrogen: Polar covalent bond
Space Filling Model Dark Gray: Carbon Light Gray: Hydrogen Red: Oxygen
Uses of Benzoic Acid • One of the most common uses of Benzoic acid is as a food preservative. • It is used to preserve many different kinds of foods, including fruit juices, soft drinks, pickles, and salad dressings. • Uses for both benzoic acid and its derivatives include the pharmaceuticals and synthetic polymers.
Uses of Benzoic Acid (continued) • Benzoic acid is used in Whitfield’s Ointment, which is used for the treatment of fungal skin diseases such as ringworm and athlete’s foot. • Benzoic acid is found in toothpastes and mouthwashes, cosmetics, and deodorants. Whitfield’s Ointment
Uses of Benzoic Acid (continued) • Pure benzoic acid is a standard for bomb calorimetry because of its ease of purification by sublimation. • The industrial applications of Benzoic acid are as a corrosion inhibitor, as an additive to automotive engine antifreeze coolants and in other waterborne systems, as a dye intermediate, as a stabilizer in photographic processing and as a catalyst.
How is Benzoic Acid made? • Benzoic acid is prepared in the laboratory by the Grignard reaction, hydrolysis of benzonitrile (C6H5CN), or prolonged oxidation of alkyl benzenes with potassium permanganate regardless of the length of the alkyl group. • Benzoic acid is also produced commercially by partial oxidation of toluene with oxygen. This process is catalyzed by cobalt or manganese naphthenates. It uses cheap raw materials, proceeds in high yield, and is considered environmentally green.
Aspartic Acid Natasha Parekh Alexis Dabney 1st period
Name (common and proper) • Common: Aspartic Acid • Proper: 2-Aminobutanedioic acid • It is also referred to as asparaginic acid and alpha-aminosuccinic acid
Empirical Formula • C4H7NO4 • The empirical formula and the molecular formula are the same in the case of aspartic acid.
Molar Mass • 133.10268 g/mol • 36.09% C • 5.30% H • 10.52% N • 48.08% O
Structural Formula Bonds Oxygen and carbon- polar covalent Carbon and carbon –nonpolar covalent Carbon and hydrogen- nonpolar covalent Carbon and nitrogen- nonpolar covalent Nitrogen and hydrogen- polar covalent Oxygen and hydrogen- polar covalent
Aspartic acid is an amino acid that is produced in organisms This is a picture of aspartic acid
Uses of Aspartic Acid • Aspartic acid is a non-essential amino acid. It is the precursor to several amino acids. • Three letter code: ASP • Letter Code: D • Codons: GAU and GAC • It is mainly used as heart disease medicine, liver function accelerant, ammonia antidote, and fatigue eliminating medication
Uses cont. • It is found in dairy, beef, poultry, and sprouting seeds. • It is very important in the metabolism when forming different amino acids • It is needed for stamina, brain health, and removes excess ammonia and other toxins from the bloodstream • It keeps the mind sharp by increasing concentrations of NADH in the brain.
How its made • Since aspartic acid is an amino acid, it is made from natural materials. • One method for making amino acids is fermentation. During fermentation, organisms convert nutrients to many components. • Raw materials are added enabling organisms to produce amino acids • Different kinds of enzymes are also involved in the process of fermentation.