Examples of Organic Molecule Projects

Honors ChemistrySpring 2009

By Jon Ericksen and Kathryn Marbury

Dichlorophenoxyacetic Acid

(Proper)

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= 96.08H x 6= 6.06Cl x 2= 70.90 = 221.04 g/molO x 3= 48.00

C

C

CC

C

CO

C

C

O

OH

Cyclo Hexyl GroupAlcohol

Structural Formula

Ethyl GroupCl

Halide

Cl

Halide

H

H

HH

H

Polar Bond

Nonpolar Bond

Ether

O

O

OH

Cl

Cl

Skeletal Formula

Carbon

Oxygen

Chlorine

Hydrogen

Space-Filling Formula

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; Que Hee & 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’dAmine salts are obtained by reacting stoichiometric quantities of amine and 2,4-D in a compatible solvent (Que Hee & Sutherland, 1974, 1981). Esters are formed by acid-catalysed esterification with azeotropic distillation of water (Que Hee & 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).

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.

History

ASCORBIC ACIDCAITLIN ACAP

PATRICK WALKER

NAMES

PROPERL-3-Ketothreohexuronic acid lactone3-keto-L-gulofuranolactone 3-oxo-L-gulofuranolactone L-threo-hex-2-enonic acid, gamma lactone

COMMONVitamin C L-ascorbic acid L-xyloascorbic acid Antiscorbutic vitamin Antiscorbic vitamin

EMPIRICAL FORMULA

C3H4O3

MOLECULAR FORMULA

C6H8O6

MOLAR MASS

C6= 12.011 x 6 = 72.066H8= 1.008 x 8 = 8.064O6= 15.999 x 6 = 95.994

72.0668.064

95.994176.124 g/mol

STRUCTURAL FORMULA

Functional Group: Ester

Hexyl Carbon Group

Alcohol (4)Alkene

SKELETAL FORMULA

SPACE FILLING FORMULA

ASCORBIC ACID

Oxygen and Hydrogen: Polar Covalent Bond Carbon and Hydrogen: Nonpolar Covalent bond Carbon and Carbon: Nonpolar Covalent Bond Carbon and Oxygen: Polar Covalent Bond

KEY: (HOMEMADE MODEL)•Carbon=Blue•Hydrogen=Red•Oxygen= Green

KEY:(INTERNET MODEL)•Carbon=Blue•Hydrogen-White•Oxygen=Red

WHAT ARE THE USES FOR ASCORBIC ACID?

1. 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.

2. Ascorbic acid is easily oxidized and is used as a reductant in photographic developer solutions (among others) and as a preservative.

3. A vitamin used in preventing scurvy, as a strong reducing agent and as an antioxidant.

4. 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.

5. Ascorbic acid prevents damage from oxygen free radicals. 6. 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.

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

C₇H₆0₂C₆H₅COOH

Molar Mass

122.12 g/molC₇= 12.01115 x 7= 84.07805 84.07805H₆= 1.0079 x 6= 6.0474 6.0474O₂= 15.9994 x 2= 31.9988 +31.9988

122.12425 ≈122.12

Structural Formula O

C CC C O H C C C Carbon-Carbon: Non-polar covalent bond

Carbon-Oxygen: Polar CovalentCarbon-Hydrogen: Non-polar covalent bondOxygen-Hydrogen: Polar covalent bond

Phenyl carbon group

Carboxylic Acid (Functional Group)

Skeletal Formula

Space Filling Model

Dark Gray: CarbonLight 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.

Fruit Juices

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 FormulaBonds

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

Skeletal Formula

Aspartic acid is an amino acid that is produced in organisms

This is a picture of aspartic acid

Space filling Formula

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.

A bottle of Aspartic Acid

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.

Vanillin4-hydroxy-3-

methoxybenzaldehyde

Empirical Formula/Molecular

Formula

C8H8O3

Molar MassC8 = 12.01x 6 = 72.06

H8 = 1.01 x 8 = 8.08

O3 = 16.00 x 3 = 48.00

128.14 g/mol

Structural Formula

All bonds are covalent bonds.

Skeletal Formula

Space Filling Formula

Uses•A flavoring in sweet foods such as

ice cream and chocolate.

Uses Contd.

•Perfume

•To hide the taste of medicine

•Livestock fodder

•Cleaning products

How it’s MadeThe Chemical WayThe demand for vanilla flavoring has long exceeded the

supply of vanilla beans. Because of this, vanillin now can be made through chemical synthesis. Vanillin was first synthesized from eugenol. Later it was synthesized from lignin-containing "brown liquor", a byproduct of the sulfite process for making wood pulp, but the lignin process is no longer popular because of environmental concerns. Today most vanillin is produced from the petrochemical raw material guaiacol. Several routes exist for synthesizing vanillin from guaiacol. At present, the most significant of these is the two-step process in which guaiacol reacts with glyoxylic acid by electrophilic aromatic substitution. The resulting vanilmandelic acid is then converted to vanillin by oxidative decarboxylation. In October 2007, Mayu Yamamoto of the International Medical Center of Japan developed a way to extract vanillin from cow dung.

How it’s MadeThe Natural Way

Natural vanillin is extracted from the seed pods of Vanilla planifola. As harvested, the green seed pods contain vanillin in the form of its β-D-glycoside. The green pods do not have the flavor or odor of vanilla. After being harvested, their flavor is developed by a months-long curing process.