O-Chem

Organic chemistry

study of compounds containing carbon

Aspirin

• acts as an analgesic (pain reliever)

• an antipyretic (fever reducer)

• an anti-inflammatory agent (inflammation reducer)

Acetaminophen

• a non-aspirin headache remedy

• an acylated aromatic amine, active ingredient in Tylenol

Ibuprofen

• active ingredient in Advil

• non-aspirin OTC drug

• acts as an analgesic (pain reliever)

• an antipyretic (fever reducer)

• an anti-inflammatory agent (inflammation reducer)

Synthesis of Heroin

an acetylation reaction

Marijuana

active ingredient is tetrahydrocannabinol (THC)

• varies in diff parts of plants

  • resin>flowers>leaves

Tetrahydrocannabinol (THC)

• binds to an unknown receptor in the brain

• inhibits the enzyme adenylate cyclase

“Magic'“ Mushrooms

• primary psychogenic alkaloid is Psilocybin

• Psilocin appears to be the primary metabolite

• Psilocybin responds to several spot tests

  • Marquis (yellow)

Analysis

spot tests

• marquis (orange)

Functional groups

are atoms, or common structural features used to classify organic molecules

Acid-Base Properties

many organic molecules contain acidic or basic functional groups

Acids

carboxylic acids (-COOH) are the most common

Bases

amines (-NH₂, -NHR, or -NR₂, where R is an organic group made up of C and H atoms) are the most common

Hydrocarbons

• consist of ONLY carbon and hydrogen

• grouped based on the number of bonds between carbon atoms

• nonpolar, insoluble in water

Four basic types of hydrocarbons:

• alkanes

• alkenes

• alkynes

• aromatic hydrocarbons

Some Simple Alkanes:

• methane (CH4): natural gas

• propane (C₃H₈): bottled gas

• butane (C₄H₁₀): disposable lighters and fuel canisters for camping

• alkanes with 5 to 12 C atoms: gasoline

Reactions of Alkanes

• relatively unreactive due to the lack of polarity and presence of only C-C and C-H a bonds, which are very stable

• don’t react w/ acids, bases, or oxidizing agents

Saturated

hydrocarbons with single bonds only

• are alkanes

Unsaturated

Alkenes, alkynes, and aromatic hydrocarbons have fewer hydrogen atoms than alkanes with the same number of carbon atoms

• more reactive

Alkenes

• contains at least one C=C bond

• no free rotation about the double bond

Alkynes

• contains at least one C triple C

• unsaturated

Aromatic Hydrocarbons

have 6 membered rings containing localized and delocalized electrons

Aromatic Nomenclature

• 1,2 = ortho-

• 1,3 = meta-

• 1,4 = para-

Alcohols

contain one or more -OH group (the alcohol group or the hydroxyl group)

Methanol

used as a fuel additive

Polar molecules

lead to water solubility and higher boiling points

Ethanol

in alcoholic beverages

Ethylene glycol

In antifreeze

Glycerol

cosmetic skin softener and food moisturizer

Phenol

making plastics and dyes; topical anesthetic in throat sprays

Cholesterol

important biomolecule in membranes, but can precipitate and form gallstones or block blood vessels

Ethers

• R-O-R

• formed by dehydration between alcohol molecules

• not very reactive (except combustion)

• used as solvents for organic reactions

Functional Groups containing the Carbonyl Group (C=O)

• aldehydes

• ketones

• carboxylic acids

• esters

• amides

Chirality

• carbons with four different groups attached to them

• are optical isomers, or enantiomers

  • have same physical & chemical properties when they react w/nonchiral reagents

Stereoisomers

constructions with different spatial arrangements

Enantiomers

Stereoisomers that have not super imposable mirror images

CHirality

property of molecules that have not super imposable mirror images

Homochiral

samples containing only one enantiomer

Optically Pure

samples that have only one of the enantiomers

Diastereomers

Stereoisomers that are not enantiomers

Racemic Mixture

samples containing equal amount of two enantiomer. They only show zero net rotation

Conformation

different molecular spatial arrangement as a result of facile rotation about single bond

Atropisomers

Stereoisomers that rotation about single bond is restricted by steric or other factors. The different conformations can be separated