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O Chem Test 3
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44
Organic Chemistry
Undergraduate 3
11/30/2010

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Term
The suffix for two carboxyl groups in one molecule.
Definition
-dioic acid
Term
Common Names For Different C chain length acids. 1-6, 8, 10, 16, and 18
Definition
Formic Acid
Acetic Acid
Propionic Acid
Butyric Acid
Valeric Acid
Caproic Acid
Caprylic Acid '6
Capric Acid '8
Palmitic Acid m-(CH2)14COOH
Stearic Acid m-(CH2)16COOH
Term
Toluic Acid
Definition
Benzoic Acid with a methyl group.
Term
What are the three terms used to describe where something is relatively in a ring?
Definition
Ortho one o'clock
Meta 4 o'clock
Para 6 o'clock
Term
Pthalic Acid
Definition
Benzoic Ring with two carboxyls in an ortho arrangement.
Term
Garbage Bags From Potato Peels Perspective (6)
Definition
We recycle biodegradable materials in plastic bags that themselves are not biodegradable.

Lab research has come up with a solution to this problem by making a bag with the properties of plastic but is still biodegradable. One example being PLA or Polylactic Acid (show how it's made), which can be used for trash bags, sutures, implants, and drug delivery systems.

Normally we waste around 10 billion lbs of potatoes each year. Potato waste however can be converted to glucose, and then lactic acid.

Nature provides other biodegradable plastics such as PHB or polyhydrobutyric acid from bacteria. It is made up of the monomer B-hydroxybutyric acid (show how it's made).

Unfortuneately PHB isn't a commercially successful plastic, so the heteropolymer Bipol is made from B-hydroxybutyric acid and B-hydroxyvaleric acid (show Bipol heteropolymer construction).

Biodegradable plastics however cannot currently compete with non-biodegradable plastics however because the bacteria that produce them do so too slowly, so future R&D is needed to reduce the cost to make them.
Term
Progressive Oxidation to Carbox Acid
Definition
primary -ol -> -al -> -oic

Perparation of a Carboxylic Acid
Term
Adipic Acid
Definition
COOH(CH2)4COOH
Term
Tartaric Acid
and
Malic Acid
Definition
COOH(CHOH)2COOH

'CH2CHOH'
Term
Oxalic Acid
Definition
OH-C=O
OH-C=O
Term
Salicylic Acid
and
Acetylsalicylic Acid
Definition
Benzoic Ring Ortho Alcohol

Benzoic Ring with ortho acetate group
Term
Carbox Dissociation
Definition
SHOULD BE DRAWN WITH AN EQUILIBRUIM <-> SIGN
Term
Esterification
& It's Reverse Rxn
Definition
R1-Carbox + R2OH <--Acid, Heat--> R1-Ester-R2 + H2O

Reverse is Hydrolysis
Term
The Chemistry of Flavor and Fragrance Perspective (3)
Definition
Carboxylic Acids Smell Very Bad. Butryic Acid is the smell of gangrene and rancid butter.

Esters however smell good as Ethyl Butyrate is the smell of pineapples.

Although fruits have a complex mixture of esters so the flavor is never fully embodied, scientists make fruit based artificial flavors made of esters that taste and smell good. One such example is Methyl butanoate (CH3CH2CH2esterCH3) which is the main ester responsible for the taste of apples.
Term
Saponification
Definition
R1-ester-R2 + H2O --NaOH or KOH, Heat--> R1-Carbox Salt + R2OH
Term
Soap From a Triglyceride
Definition
CH2-oester-R1
CH-oester-R2
CH2-oester-R3 --M+OH-, Heat, H2O--> Glycerol + R1-ester-M + R2-ester-M + R3-Ester-M

Glycerol
CH2-OH
CH-OH
CH2-OH
Term
How soap works.

What is the name of the units it forms?
Definition
The polar hydrophilic heads dissolve in the water, while the non-polar hydrophobic tails that dissolve in the oil. This forms micelles. The micelles then bring the oil within them as they are washed away.
Term
PETE formation (P.475)
Definition
COOH-Benzene-COOH + 1,2 Ethanediol --> H2O + HOCH2CH2-oester-benzene-COOH --> same thing happens on the other side.
Term
Acid Chloride Formation (p.476)
Definition
R-Carbox --Inorganic Acid Chloride-->
O
R-C-Cl + Inorganic products
Term
Anhydride Formation (write out, on p.479)
Definition
R1-Acid Chloride --R2-Carbox Ion-->
R1-Acid anhydride-R2 + Chloride Ion
Term
Examples of Inorganic Acid Chlorides (3)
Definition
PCl3, PCl5, SOCl2
Term
Ethanoic Anhydride
Benzoic Anhydride (both p. 479)
Definition
m-Anhydride-m
Benzene-Anhydride-Benzene
Term
What happens when you mix an alcohol with an anhydride? (p. 481)
Definition
ROH + R-Acid anhydride-R --> R-Ester-R + R-Carbox
Term
O
m-C-Cl
Definition
Ethanoyl Chloride
Term
The 8 Groups of ATP
Definition
Adenosine, Phosphate, Amine, Purine, Hydroxyl, (Phospho) Anhydride, (Phospho) ester, Furan
Term
Thioester
Definition
O
R1-S-C-R2
Term
Phosphate Group
Definition
O
||
HO-P-O-
OH
Term
Carboxyllic Acid Derivatives of Special Interest Perspective (6) p.484 for molecules
Definition
Asprin or acetylsalicylic acid is derived from the bark of the willow tree is the most widely used drug in the world with hundreds of millions of dollars being spent on it each year. It is both an analgesic or pain reliever, and an antipyretic or fever reducer.

It is among a group of molecules known as NSAIDs, or nonsteriodal anti-inflammatory drugs. These drugs inhibit cyclooxygenase which helps synthesize prostaglandins which are in part responsible for pain and fever.

Because NSAIDS inhibit clotting, they are not recommended for pregnant women or those with ulcurs. In those cases acetaminophen (draw structure) or tylenol is prescribed.

In the search for molecules with the same effects but are gentler on the stomach, Ibuprofen and naproxen were found.

Pheromones are chemicals secreted by animals that affect the behavior of the same species. These can be involved in warning, sexual attraction, trail marking. Insect pheromones are studied the most as they are often carboxylic acids, or acid derivatives. Tetracecenyl Acetate: m-CH2CH=CH(CH2)9CH2-oester-m
Term
ROH + Phosphoric Acid --> (p.482)
Definition
R-Phosphate Ester + H2O
Term
Give an Example of a _____

Acetyl CoA is a _____
Definition
Thioester CoA--SH
Term
Carbon Chain Names with Amine Group 0-6
Definition
Ammonia
Systematic & Common
Methanamine Methylamine
N-Methylmethanamine Dimethylamine
N,N-Dimethylmethanamine Trimethylamine
Ethanamine Ethylamine
Propanamine Propylamine
Butanamine Butylamine
Term
Toluidine (draw p. 499)
Definition
Aniline with a methane group in the o m or p position.
Term
Sulfanilamide (p.502)
Definition
Term
General: Preparation of Amines
Specifics (2)
Amide to Amine Rxn (p.522)

Nitrocompound to Aromatic primary amine (p. 522)
Definition
Term
Basicity of Amines Demonstration

(P. 522)
Definition
Amine + Water <--> Alyklammonium ion + Hydroxide ion
Term
Neutralization of Amines (P. 522)
Definition
Amine R-NH2 + Acid HCl --> Alkylammonium salt
Term
The other name for an amide bond.

Also, what is an amide bond?(ec)
Definition
Peptide bond
Term
How polar and soluble are esters?
Definition
Mildly polar, and somewhat soluble.
Term
General: Preparation of Amides
Specific: 2 (p. 522)

1

2
Definition
Acid Chloride + 2 Ammonia or Amine --> Amide + Ammonium Chloride or Alkylammonium chloride.

R1-Acid Anhdride-R2 + Ammonia or Amine --> Amide + R-COO- NH4+
Term
General: Hydrolysis of Amides
2 Specifics (p. 522)
Definition
R-Amide-R1 + Strong Acid H3O+ --> R-COOH + R-NH3+

R-Amide-R1 + Strong Base --> Carbox Salt R1-COO- M+ + R2-NH2 Amine
Term
Semisynthetic Penicillins Perspective (4)
Definition
The first antibiotic: penicillin, was discovered by Alexander Flemming in 1929. The first antibiotics were only effective against Gram positive bacteria and were susceptible to bacterial enzyme destruction and stomach acid.

To overcome these issues, chemists created semisynthetic penicillins that maintain the B-lactam ring which is what gives antibiotics their properties. Where the deviations exist are in the R group that determines the degree of antibacterial activity.

Chemists use an enzyme called amidase to remove the amide bond and then replace the R group and test the properties of the new antibiotic.

Among these newer antibiotics are ampicillin, methicillin, and oxacillin.
Term
Give an Account on Medically Important Amides (3) Draw Structure for Barbital, acetaminophen, and phenacetin (p. 512)
Definition
Barbiturates or 'downers' are derived from amides and used as sedatives. They are also anticonvulsants for epilepsy and people suffering from other brain disorders that cause neurosis, anxiety, and tension.

Acetaminophen, an aromatic amide first synthesized in 1893 is used in place of aspirin in the case of those who may be allergic or unable to handle apsirin in their stomachs. It is the active ingredient in tylenol and datril. Acetaminophen relieves fever and pain but is not anti-inflammatory.

Phenacetin, first synthesized in 1887 is used as an analgesic and is similar in structure to acetaminophen. It was banned in 1983 however because of kidney damage and blood disorders it causes.
Term
Draw the resonance of an Amide (p. 510)
Definition
Term
EC: Draw Imidizole, Pyridine, Pyrrole, and Pyrimidine (p. 507)
Definition
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