WEEK 13 - Alcohol and Phenols

Alcohols

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

alkyl group

In common names, the separate word “alcohol” is placed after the name of the?

MONOhydric

what kind of classification

Dihydric

what kind of classification

TRihydric

what kind of classification

Allylic carbon atom

what kind of CARBON ATOM

Benzylic carbon atom

what kind of CARBON ATOM

colorless liquids at room temperature.

Most of the common alcohols are

4-10

Higher alcohols containing HOW MANY atoms

• viscous or oily

• heavy fruity odors

Higher alcohols (4-10) somewhat?

12

Highly branched alcohols containing more than HOW MANY carbon atoms are solids at room temperature.

solids at room temperature.

highly branched alcohols containing more than 12 carbon atoms are?

hydrophilic (“water-loving”)

hydroxyl group is referred to as a

• Methanol

• ethanol

• n-propyl alcohol

• isopropyl

alcohol are all miscible with water.

less water-soluble

Alcohols with higher molecular weights tend to be

4

lower alcohols with UP to HOW MANY carbon atoms

Methanol

Very soluble in water

Butanol

Slightly soluble in water

Octanol

Insoluble in water

wood by distillation

Methanol was at one time produced from?

wood alcohol

Methanol sometimes called?

• carbon monoxide

• hydrogen

Methanol is manufactured from

Methanol

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

Formaldehyde

Methanol Oxidized what?

Opsin

Formaldehyde bind to?

rhodopsin,

formaldehyde, which binds to opsin, preventing formation of?

rhodopsin

the light-sensitive pigment neededforvision.

Methanol

highly toxic and can cause permanent blindness

Mild CNS depression

Cinical Effects of Methanol Intoxication:

Early CNS

• Vertigo

• lethargy

• coma,

• Parkinson-like syndrome

• putamen necrosis

• Hemorrhage

Clinical Effects of Methanol Intoxication:

Late CNS

• Photophobia

• retinal edema

• blindness

Clinical Effects of Methanol Intoxication:

Late VISION

• Abdominal pain

• pancreatitis

Clinical Effects of Methanol Intoxication:

Late GI

AKI (rare)

Clinical Effects of Methanol Intoxication:

Late KIDNEY

Ethanol

used in fermentation

Yeast

Fermantation catalyst

acid-catalyzed hydration of ethylene

Beside fermentation ETHANOL manufactured by the

Sulfuric acid

acid-catalyzed hydration of ethylene CATALYST

Ethanol

used as a solvent, as a topical antiseptic (for example, when drawing blood).

Ethanol

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

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.

• 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.

• Dehydration

• Oxidation

• Substitution

• Esterification

Chemical Reaction in ALCOHOL

• ketones

• aldehydes

• carboxylic acids.

Alcohols may be oxidized to give

phenol

In 1865 the British surgeon Joseph Lister used as an antiseptic to sterilize his operating field.

1865

In WHAT YEAR British surgeon Joseph Lister used phenol as an antiseptic to sterilize his operating field.

Joseph Lister

WHO IS THE British surgeon THAT used phenol as an antiseptic to sterilize his operating field.

Phenol

Joseph Lister used WHAT as an antiseptic to sterilize his operating field.