Honors Chemistry
Spring 2009
Dichlorophenoxyacetic
Acid
(Proper)
By Jon Ericksen and Kathryn Marbury
*2,4-D
*Weedtrine-II
*Aqua-Kleen
*Barrage
*Plantgard
*Lawn-Keep
*Planotox
*Malerbane.
C8H6Cl2O3
C x 8= 96.08
H x 6= 6.06
Cl x 2= 70.90
O x 3= 48.00
= 221.04 g/mol
H
H
Halide
C
H
C
Ether
O
Cl
C
C
O
C
C
OH
H
C
C
H
Cl
Ethyl Group
Alcohol
Cyclo Hexyl Group
Halide
Polar Bond
Nonpolar Bond
Structural Formula
O
O
Cl
OH
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 brandname 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 2,4dichlorophenol 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’d
Amine 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 acidcatalysed 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).
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. 2,4D 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
NAMES
PROPER
L-3Ketothreohexuronic
acid lactone
3-keto-Lgulofuranolactone
3-oxo-Lgulofuranolactone
L-threo-hex-2-enonic
acid, gamma lactone
COMMON
Vitamin C
L-ascorbic acid
L-xyloascorbic acid
Antiscorbutic vitamin
Antiscorbic vitamin
EMPIRICAL FORMULA
C3H4O3
MOLECULAR FORMULA
C6H8O6
MOLAR MASS
C6= 12.011 x 6 = 72.066
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
SKELETAL FORMULA
SPACE FILLING FORMULA
ASCORBIC ACID




KEY:
(HOMEMADE MODEL)
KEY:
(INTERNET MODEL)
•Carbon=Blue
•Hydrogen=Red
•Oxygen= Green
•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
WHAT ARE THE USES FOR
ASCORBIC ACID?
1.
2.
3.
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.
4.
5.
6.
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, Preeclampsia, 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
C₇H₆0₂
C₆H₅COOH
Molar Mass
122.12 g/mol
C₇= 12.01115 x 7= 84.07805
H₆= 1.0079 x 6= 6.0474
O₂= 15.9994 x 2= 31.9988
122.12425
≈122.12
84.07805
6.0474
+31.9988
Structural Formula
Carboxylic Acid
(Functional Group)
O
Phenyl carbon group
C
C
C
C
C
C
C
O
H
Carbon-Carbon: Non-polar covalent bond
Carbon-Oxygen: Polar Covalent
Carbon-Hydrogen: Non-polar covalent bond
Oxygen-Hydrogen: Polar covalent bond
Skeletal Formula
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.
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
Formula
Bonds
Oxygen and carbon- polar
covalent
Carbon and carbon –nonpolar
covalent
Carbon and hydrogennonpolar 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.
Vanillin
4-hydroxy-3-methoxybenzaldehyde
Empirical
Formula/Molecular
Formula
C8H8O3
Molar Mass
C8 = 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 Made
The Chemical Way
The 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 Made
The 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-Dglycoside. 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.