ORG CHEM LAB - EXP #10 - 12

CARBOXYLIC ACID

is an organic compound containing a carboxyl functional group

CARBOXYL FUNCTIONAL GROUP

a functional group consisting of a carbon atom that is double bonded with an oxygen atom and singly bonded to a hydroxyl group (R-is the rest of molecules which this group is attached)

CARBONYL GROUP

composed of carbon atom double bonded with oxygen atom only

OMEGA-6 & OMEGA 3

essential fatty acids - not produced by our body (we have to obtain this from our food); help maintain cell membranes and control nutrients along with our metabolism

STEARIC ACID

carboxylic acid is used for manufacturing of soaps -- sodium or potassium salts of higher fatty acids such as _______________

ASA

Acetylsalicylic Acid (Aspirin)

ACETIC ACIDS

are often used as a coagulant in the manufacturing of rubber

ACETIC ACIDS

• one type of carboxylic acid

• second most common carboxylic acid

• also known as ethanoic acid

• also the compound responsible for the sour taste of vinegar

CARBOXYLIC ACID AND THEIR DERIVATIVES

these are organic compounds containing the acyl group core structure attached to a Y group

AMIDE

is a functional group containing a carbonyl group linked to a nitrogen atom or any compound containing the amide functional group

AMIDE

when an amino group replaces the OH group of carboxylic acid = resulting compound: ______________; derived from the reaction of carboxylic acid and an amine

Carboxamides, sulfonamides, and phosphoramide

examples of amides

LSD, Penicillin, and paracetamol

several drugs are amides including..

Lysergic Acid Diethylamide (LSD)

• one of the most potent mood changing chemicals

• manufactured for Lysergic acid found in ergot fungus (grows on rye and other grains)

Nylon

polyamide

Kevlar

super strong plastic used for making boats and boat strings and in other materials/products

Dimethylformamide

is an important organic solvent (for chemical reactions such as extraction/isolation of chlorophyll from plant tissues)

ACYL HALIDE

another name for Acid Halide

ACID HALIDE

is an organic compound derived from carboxylic acids by replacing a hydroxyl group with a halide group

ACID ANHYDRIDE

• is formed from the dehydration reaction of two carboxylic acid groups

• replaces OH with O(C=O)R

ACETIC ANHYDRIDE

• one of the simplest acid anhydrides and widely used as a reagent in organic synthesis

• colorless liquid that smells strongly of acetic acid

• it is used in the production of aspirin (ASA), which is prepared by the acetylation of salicylic acid

• used in the synthesis of heroin by the diacetylation of morphine

United States Drug Enforcement Administration List II Precursor

chemicals which are restricted chemicals in many other countries

LEOPOLD GMELIN

the term "ester was coined by the German chemist in 1848

ESSIGATHER

contracted German word meaning acetic ether

ESTER

the hydrogen of the carboxyl group is replaced with hydrocarbon group (R')

FATS AND OILS

are examples of esters; the difference between them is the melting point of their esters

OIL

if it is liquid at room temperature (ex: vegetable oil)

FAT

if it is solid at room temperature (ex: butter and Lard)

CARBOXYLIC ACID

CARBOXYLIC ACID

found or used in: vinegar, cream of tartar

AMIDE

AMIDE

found or used in: nylon, proteins

ACYL CHLORIDE (ACYL HALIDE)

ACYL CHLORIDE (ACYL HALIDE) & ACID ANHYDRIDE

found or used in: synthesis of carboxyl derivative

ACID ANHYDRIDE

ESTER

ESTER

found or used in: fats, cell membranes

"hydro"

water

"lysis"

to break down

HYDROLYSIS

• process of using water to break down bonds of a molecule or a substance

• reaction of organic material and water

SCHOTTEN-BAUMANN REACTION

alcoholysis is also known as _______________

Carl Schotten and Eugen Baumann

this organic chemical reaction (alcoholysis) is named after the German chemists ________________________

SCHOTTEN-BAUMANN REACTION

• is defined as a reaction that occurs between an organic molecule and an alcohol (such as ethanol)

• cleavage (splitting) of chemical bonds of an organic compound with an alcohol

ANILIDE FORMATION

aminolysis is also known as _________________

ANILIDE FORMATION

• any chemical compound reacting with a molecule of ammonia/amine which causes a split into two parts

HYDROXAMIC ACID TEST

test for esters

(+) warming effect

positive result for Acyl Halides & Acid Anhydrides with water (hydrolysis)

(+) white ppt

positive result for Acyl Halides AgNO3 (hydrolysis)

turbid solution

positive result for Acid Anhydrides with AgNO3 (hydrolysis)

(+) Effervescence (bubbling effect)

positive result for Acyl Halides & Acid Anhydrides with saturated NaHCO3 (hydrolysis)

clear colorless solution with plastic balloon-like odor

positive result for Esters with 25% NaOH then 10% HCl (hydrolysis)

Red litmus → blue (basic) indicating ammonia gas

positive result for Amides with 10% NaOH (hydrolysis)

fruity odor - resulted to the production of ethyl acetate (ester)

positive result for Acetic acid with 1mL ethanol & 5 drops conc. H2SO4 (alcoholysis)

fruity odor - yielded ethyl ethanoate (ester)

positive result for Acyl Halides & Acid Anhydrides with 0.5mL ethanol & 2mL of 20% NaOH (alcoholysis)

formation of white ppt with oily layer (yielded anilide upon addition of water)

• presence of anilide in the mixture

positive result for Acyl Halides & Acid Anhydrides with 0.5mL aniline (aminolysis)

(+) deep burgundy color (upon being heated w/ NH2OH . HCl → both converted to hydroxamic acid)

positive result for Ethyl acetate and Acetamide with NH2OH . HCl & 1M KOH + 1mL of 5% FeCl3 (hydroxamic acid test)

AMINES

• are the ammonia (NH3) derivatives of hydrocarbons

• have a characteristic of fish odor and lighter than water

• their boiling points are lower than those of alcohol or carboxylic acids of comparable masses

• can form hydrogen bond

ALIPHATIC AMINES/ALKYL AMINES

amines connected to an alkyl chain

• demonstrate solubility in organic polar solvents

AROMATIC AMINES/ARYL AMINES

amines that participate in a conjugated ring

• display less solubility in water because of the presence of aromatic groups (non-polar)

REDUCTION

reaction that involves loss of oxygen

SUBSTITUTION

an atom/functional group is replaced by another atom/functional group

HOFMANN REARRANGEMENT

primary amide is converted into primary amine (made to react with halogen (Br/Cl) in basic aqueous environment (NaOH/KOH)

TETRAMETHYLAMMONIUM IODIDE

we use ____________________ for disinfecting water

MORPHINE AND MEPERIDINE (DEMEROL)

opioid analgesics (relief of moderate to severe pain)

NOVOCAINE

used as anesthetic -- "first injectable synthetic local anesthetic"

EPHEDRINE

is a very common decongestant

CHOLINE

• is one of the salts which plays a significant role in the production of neurotransmitters in human body to make the brain function properly

ACETYLCHOLINE

• choline is the precursor to ____________-

• neurotransmitter (messenger between the nerves = important for brain and muscle)

PRIMARY AMINES

• only one of the hydrogen atoms in the ammonia molecule has been replaced (can be an alkyl group / aromatic substituents)

METHYLAMINE

most common primary amine

METHANAMINE

IUPAC name for methylamine

SECONDARY AMINES

two of the hydrogen in an ammonia molecules have been replaced by hydrocarbon

TERTIARY AMINES

all the hydrogens in an ammonia molecule have been replaced by hydrocarbon groups

BENZENE SULFONYL CHLORIDE

HINSBERG'S TEST reagent?

HINSBERG TEST

determine sample is primary, secondary, tertiary amine

OSCAR HEINRICH DANIEL HINSBERG

it was named after him the Hinsberg test - first described the reaction (1890)

Sulfonamide product is soluble in alkali (NaOH)

result of primary amine in Hinsberg test

Sulfonamide product is NOT soluble in alkali (NaOH)

result of secondary amine in Hinsberg test

No such reaction

_________________________ occurs between a tertiary amine and the benzene sulfonyl chloride reagent; help in hydrolysis of sulfonyl chloride (this reaction yields salt that are soluble in water) = immediately form salt that dissolves -- no ppt

ACETYLSALICYLIC ACID (ASPIRIN)

acetyl ester derivative of salicylic acid / carboxylic acid / ester

C9H8O4

chemical formula of aspirin

180.154 g/mol

molecular weight of aspirin

Colorless to white crystalline solid

appearance of aspirin

Vinegar odor

odor of aspirin

Spiraea ulmaria

Filipendula Ulmaria; former classified as ___________

Meadowsweet (Filipendula ulmaria)

Aspirin was isolated from ____________________; by German researchers in 1839 (diarrhea, stomach irritation, gastrointestinal effects -- high doses = death)

Charles Frederic Gerhardt

in 1853, a French chemist neutralized salicylic acid by buffering it with sodium (sodium salicylate) and acetyl chloride creating acetosalicylic anhydride (no irritation)

Arthur Eichengrun and Felix Hoffman

in 1897, researchers _____________and _______________, a research assistant at Friedrich Bayer & Co. in Germany, derivatized one of the hydroxyl functional groups of salicylic acid with an acetyl group (forming the acetyl ester)

First synthetic drug

Aspirin was the ___________________, not a copy of something that existed in nature, and the start of the pharmaceutical industry

Raffaele Piria

first isolate aspirin in crystalline form

ASA

abbreviation of aspirin

STARCH BINDER

in commercial aspirin products, a small amount of aspirin is bound together with a ______________, and sometimes with caffeine and buffers; excipient (hold ingredients together)

Enteric coated

the basic conditions in the small intestine (7.00-8.5) break down the aspirin to yield salicylic acid which is absorbed in the bloodstream (small intestine not stomach) -- protect from stomach acid

Cyclooxygenase (COX)

Aspirin acts as an inhibitor of _____________________ which results in the inhibition of prostaglandins

• responsible for converting arachidonic acid to prostaglandins

PROSTAGLANDINS

play a key role in inflammation, pain, fever

Platelet aggregation

aspirin also inhibits _____________ and is used in the prevention of arterial and venous thrombosis

Kawasaki disease

• acute, febrile (fever) condition that usually affect children less than 5 y.o (unknown cause)

• inflammation of blood vessels throughout the body

Tomisaku Kawasaki

in 1967, first describe Kawasaki disease in Japan

Reye's syndrome

acute increase in pressure in the brain and also causes accumulation of fat in the liver and other organs

Dyspepsia

side effects of aspirin meaning indigestion