PORG (FINALS): Alcohols and phenols

Alcohols

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

R-OH

Alkyl group

General representation of Alcohol and group

enols

sp2-hybridized carbon are called ____

primary alcohol (1°)

R-CHOH

Secondary alcohol (2°)

R

|

R- CHOH

tertiary alcohol (3°)

R

R-C—OH

R

Monohydric

Contains only one -OH group

Dihydric

Contains two OH groups

Trihydric

Contains three -OH groups.

alpha carbon

carbon atom that is directly bonded to a functional group

Allylic carbon atom

Carbon adjacent to a C=C double bond

benzylic carbon atom

next to a benzene ring

colorless

Most of the common alcohols are ____ liquids at room temperature.

viscous or oily

fruity

Higher alcohols - those containing 4-10 atoms - are somewhat ____, they have heavy _____ odors.

solids

Some of the highly branched alcohols containing more than 12 carbon atoms are ______ at room temperature

higher

boiling points of alcohols are much ______ than those of alkanes with similar molecular weights.

hydrophilic ("water-loving")

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

Methanol,

ethanol,

n-propyl alcohol,

isopropyl alcohol

Alcohols that are miscible with water.

higher-less

Alcohols with _____ molecular weights tend to be _____ water-soluble,

because the hydrocarbon part of the molecule, which is hydrophobic ("water-hating"), is larger with increased molecular weight.

lower alcohols

(those with up to 4 carbon atoms) are manufactured on a large scale.

They are used as raw materials for other valuable chemicals and also have important uses in their own right.

1. Methanol

2. Ethanol

3. Isopropyl Alcohol

4. Ethylene Glycol

5. Glycerol

Lower alcohol that important in pharmaceuticals (5)

Methanol

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

carbon monoxide and 2 hydrogen

At present, methanol is manufactured from ____ and ____

zinc oxide

chromium oxide

400*C, 150 atm

Catalyst use to make methanol in present days.

And celsius and atm need

Methanol

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

permanent blindness

Methanol is highly toxic and can cause _____

Aldehyde or formaldehyde

Sumisira sa opsin that prevents formation of rhodopsin

Opsin

Universal photoreceptor

rhodopsin

Responsible for light-sensitive pigment needed for vision

Dehydrogenation

Oxidation also called

Antizol

Fomepizole B.N

-antidote for MeOH/ ethylene glycol poisoning

Methanol- Aldehyde-COOH

Methanol metabolism

Mild CNS depression

Cinical Effects of Methanol Intoxication: Early

CNS

Vertigo,

lethargy, coma,

Parkinson-like syndrome,

putamen necrosis,

hemorrhage

Cinical Effects of Methanol Intoxication: Late

CNS

Photophobia, retinal edema, blindness

Cinical Effects of Methanol Intoxication: Late

Vision

Abdominal pain, pancreatitis

Cinical Effects of Methanol Intoxication: Late

GI

AKI (acute kidney injury) rare

Cinical Effects of Methanol Intoxication: Late

KIDNEY

Ethyl alcohol (ethanol)

Can drink by fermented

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.

Cane (fruit) sugar + Water H2O

Yeast

How to make ethanol and catalyst

acid-catalyzed hydration

Besides fermentation, ethanol is also manufactured by the _____ of ethylene.

proof

term used in the United States in

reference to alcoholic beverages

Ethanol

is used as solvent, as a topical antiseptic (prevent the growth of disease-causing microorganisms.)

(for example, when drawing blood).

It also can be used as a fuel, often as a blend with gasoline.

nicotinamide adenine dinucleotide (NAD+)

ELECTRON ACCEPTOR, carries hydrogen and converted into NADH

nicotinamide adenine dinucleotide (NAD) + hydrogen (H).

NADH 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

ETHANOL EFFECTS TO HUMANS:

Loss of balance and speech, amnesia

300-400mg/dL

ETHANOL EFFECTS TO HUMANS:

N/V, loss of consciousness

400-600mg/dL

ETHANOL EFFECTS TO HUMANS:

Loss of protective reflexes

600mg/dL

ETHANOL EFFECTS TO HUMANS:

Spontaneous respiration,

CV problems, death

2-Propanol (isopropyl alcohol)

manufactured commercially by the acid-catalyzed hydration of propene

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

ethylene glycol

refers literally to "the glycol made from ethylene."

Ethylene glycol

commonly used as automotive antifreeze and as an ingredient in hydraulic fluids, printing inks, and paint solvents

Glycerol

is a sweet syrupy substance with three alcohol hydroxyl groups.

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

1. Oxidation

2. Dehydration

3. Substitution

4. Esterification

Chemical Reactions: (4)

Alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis

ketones

aldehydes,

carboxylic acids

Alcohols may be oxidized to give _____,_____and ____

-These functional groups are useful for further reactions; for example, ketones and aldehydes can be used in subsequent reactions, and carboxylic acids can be used for esterification

Chromic acid H2CrO4

Strong oxidizing agent for alcohol oxidation.

pyridinium chlorochromate (PCC)

-oxidizes primary alcohols to aldehydes

One at a time

Dehydration of Alcohols to Alkenes

Conversion of an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the adjacent carbon atom.

Dehydration reactions

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

intermolecular dehydration

Simple alcohols can undergo ________to give ethers

Dehydration of alcohol to ether

Most economical method for making ethyl ether

Substitution of alcohol

_____ of Alcohols

to form Alkyl Halides

Esterification

Alcohols can combine with acids to form carboxylic esters.

Remove of OH and H (H2O)

Fischer esterification

characterized by the combining of an alcohol and an acid (with acid catalysis) to yield an ester plus water.

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

Monohydroxy compounds

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

Simple monohydric phenols

are either corrosive liquids or low melting solids. The dihydric and trihydric phenols are solids.

1865 Joseph Lister

British surgeon used phenol as an antiseptic to sterilize his operating field in year ___

monohydroxybenzene (benzenol or carbolic acid)

Simplest member of phenol

45 to 15

With phenol used in this manner, the mortality rate from surgical amputations fell from ______ to _____percent in Lister's ward.

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

5-hydroxytryptamine

Sometimes referred as one of the happy hormones (endorphins and dopamine)

Urushiol

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

Vanillin

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