PORG WEEK 13 ALCOHOLS AND PHENOLS

Alcohols

Characterized by one or more hydroxyl groups attached to a carbon atom of a hydrocarbon chain

hydroxyl moiety

Alcohol Alkyl group

–ol

the hydroxyl group is indicated by the ending

saturated, sp3-hybridized carbon atom

In practice, the group name alcohol is restricted to compounds that have their -OH group bonded to a

enols

compounds with their -OH group bonded to a vinylic (-CH=CH2),

sp2-hybridized carbon are called

Carboxylic acid

Aldehyde

Ketone

Alcohol

Amine

Highest to lowest priority

allylic or benzylic

Alcohols are referred to as ______ if the hydroxyl group is bonded to an allylic carbon atom (adjacent to a C=C double bond)

Higher alcohols

those containing 4-10 atoms – are somewhat viscous or oily, they have heavy fruity odors.

solids at room temperature.

Some of the highly branched alcohols containing more than 12 carbon atoms are

higher

The boiling points of alcohols are much _____ than those of alkanes with similar molecular weights

hydrophilic (“water-loving”) group

The hydroxyl group is referred to as a ___________, because it forms hydrogen bonds with water and enhances the solubility of an alcohol in water.

miscible

Methanol, ethanol, n-propyl alcohol, isopropyl alcohol are all _____ with water.

higher

Alcohols with ____ molecular weights tend to be less water-soluble

Methanol

was at one time produced from wood by distillation and is still sometimes called wood alcohol.

Chromium oxide & Zinc oxide

150 standard atmosphere (pressure) at 400°

methanol is manufactured from carbon monoxide and hydrogen using

Methanol

Most of it is used to produce formaldehyde and other chemicals, but some is used as a solvent and as an antifreeze

Methanol

is highly toxic and can cause permanent blindness because when taken internally, it is oxidized to formaldehyde, which binds to opsin, preventing formation of rhodopsin, the light-sensitive pigment needed for vision.

Opsin

universal photoreceptor molecules of all visual systems in the animal kingdom

Rhodopsin

When opsin is damaged, it prevents the formation of ___ which is the light-sensitive pigment needed for vision.

Fomepizole (Antizol ®)

antidote for MeOH/ ethylene glycol poisoning

Formaldehyde

is responsible for carcinogenesis and age-related damage to neurons in the brain

Ethyl alcohol

has been produced mostly through the fermentation of fruit juices. The fermented juice could be stored in a sealed container, and this primitive wine remained safe to drink throughout the winter.

ethanol

is also manufactured by the acid-catalyzed hydration of ethylene.

acid-catalyzed hydration of ethylene

This method, using sulfuric acid or other acid catalysts

Antiseptic

prevent the growth of disease-causing microorganisms.

Nicotinamide adenine dinucleotide

NAD stands for

Disulfiram (Antabuse ®)

used in the treatment of alcohol use disorders by producing unpleasant side effects and sensitivity to alcohol. It is designed as a deterrent to drinking.

80-300mg/dL

Loss of balance and speech, amnesia

300-400mg/dL

N/V, loss of consciousness

400-600mg/dL

Loss of protective reflexes

600mg/dL

Spontaneous respiration, CV problems, death

2-Propanol (isopropyl alcohol)

is manufactured commercially by the acid-catalyzed hydration of propene.

2-Propanol (isopropyl alcohol)

It is the main component of rubbing alcohol and is used in many household and personal care products.

70% isopropyl alcohol

most commonly used disinfectant in pharmaceutical industries. The important thing is that only ________ acts as a disinfectant killing all surface microorganisms. It is used to disinfect hands and equipment surface in pharmaceuticals.

“the glycol made from ethylene.”

The name ethylene glycol refers literally to

ethan-1,2-diol

Ethylene glycol’s systematic name is

Poly(ethylene glycols) (or PEGs)

have been utilized in various forms in pharmaceutical preparations for many years. They are used as additives to creams, as solubilizing agents, and as components of injectable formulations.

Glycerol

is a sweet syrupy substance with three alcohol hydroxyl groups.

Glycerol

was first obtained as a by-product of soap manufacture.

Glycerol

is used in the pharmaceutical industry to prevent the drying of creams and ointments even in cough syrups to help prevent irritation in throats.

Secondary alcohols

are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.

Tertiary alcohols

cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.

Chromic acid

oxidizes primary alcohols to carboxylic acids, and it oxidizes secondary alcohols to ketones.

Tertiary alcohols

do not react with chromic acid under mild conditions.

Dehydration

are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid

Esterification of Alcohols

Called as Fischer Esterification

carboxylic esters.

Alcohols can combine with acids to form

Phenols

Any of a family of organic compounds characterized by a hydroxyl group attached to a carbon atom that is a part of an aromatic ring

Phenols

Simplest member, monohydroxybenzene

Phenols

Also known as benzenol or carbolic acid

Monohydroxy compounds

are only slightly soluble in water but are miscible with organic solvents.

Joseph Lister

In 1865 the British surgeon _____ used phenol as an antiseptic to sterilize his operating field.

Phenol

is quite toxic, however, and concentrated solutions cause severe but painless burns of the skin and mucous membranes.

Catechol

Resorcinol

Quinol

Pyrogallol

Hydroxyquinol

Phloroglucinol

n-hexylresorcinol

Less-toxic phenols, such as ____-, have supplanted phenol itself in cough drops and other antiseptic applications

Butylated hydroxytoluene (BHT)

has a much lower toxicity and is a common antioxidant in foods.

Tyrosine

One of the standard amino acids found in most proteins

Epinephrine

AKA adrenaline

Stimulant hormone produced by the adrenal medulla

Serotonin

A neurotransmitter in the brain

Urushiol

An irritant secreted by poison ivy to prevent animal from eating its leaves

Vanillin

the principal flavouring in vanilla, is isolated from vanilla beans

Methyl Salicylate

has a characteristic minty taste and odour, is isolated from wintergreen

Thymol

Extracted from Thyme

fungicidal

Eugenol

Extracted from clove oil

Antiseptic in mouthwashes

Dental analgesic