Alcohols

Front 1

alcohol

Back 1

r-oh with oh functional group

Front 2

phenol

Back 2

-Ar-OH
-c6h5 -oh group attached to benzene
-carbolic acid used as disinfectant by Lister
-weak acids
-flavoring= vanilla, cloves, nutmeg
-disenfictants for medical instruments
-antiseptic
-food preservative
-irritation in poision ivy

Front 3

ether

Back 3

-R-O-R
-no hydrogen bonding
-solubility-oxygen in ether can h bond with water, small ethers soluble in water
- nomenclature= furan=five member ring, puran=6 member ring
-physical properties=
low boiling point (no h bonds), soluble in water(h bonds with water), good solvent for organic compounds
-flammable liquids
-can form peroxides in air

Front 4

thiol

Back 4

R-SH, R-S-R(thioether)
-compounds containing SH group
-strong, distinctive odor
-named like alcohols ex 1-butane thiol
-oxidation- two thiol groups oxidized to form a disulfide group
-coenzyme a= important thiol in biological systems, catties acetyl group in carb and fat metabolism
- perm= based on disulfide bonds in hair, reducing agent breaks s bonds, oxidizing agent to form new s bonds

Front 5

diols

Back 5

-alcohol containing two alcohol groups
-used as antifreeze
-airplane deicers
-starting material for polyester films and fabrics
-lethal if ingested-oxided to oxalic acid, kidney damage
-1,2 propane diol/propylene glycol-non toxic, oxidized to pyruvic acid in liver by alcohol dehydrogenase

Front 6

triol

Back 6

-alcohol with 3 alcohol groups
-glycerol=non toxic, sweet taste, good moisturizer, aircraft deicers, biological antifreeze in fish and insects, byproduct from digestion of fats and oils, nitroglycerin and triglycerides

Front 7

important alcohol methanol

Back 7

-wood alcohol=toxic- oxidized to formaldehyde, may cause blindness
- canned heat
- fuel for race cars

Front 8

important alcohol- ethanol

Back 8

-oldest known reaction
-fermentation of grain and sugar, distilled = 14% alcohol
-hangover, cirrhosis of liver, birth defects, memory loss
- industrial alcohol-hydration of alkene
-absolute alcohol

Front 9

important alcohols- isopropyl alcohol/ 2- propanol

Back 9

-rubbing alcohol
- cool fevered patients
-astringents
-industrial solvent
-antiseptic
-toxic, oxidezed to acetone, paralysis of nervous system

Front 10

solubility of alcohols

Back 10

-small 1-4 carbons= miscible in water, hydrophilic- oh group forms hydrogen bonds with water
-larger= immicsible in water, solubility decreases as hydrophobic chain increases

Front 11

boiling/melting points of alcohol

Back 11

-high boiling points due to hydrogen bonding between alcohol molecules
-higher bp than ether or alkene with similar mass

Front 12

preparation of alcohols

Back 12

-hydrogenation(reduction) of aldehyde or ketone
-hydration of alkene

Front 13

summary of alcohol rxn

Back 13

-combustion
-dehydration=alcohol to alkene, alcohol to ether
-oxidation

Front 14

dehydration- alcohol to alkene

Back 14

-elimination reaction= water eliminated from alcohol
-acid catalyst- h2so4 and 180° required
-multiple products= zaitsevs rule= loss of hydrogen from carbon with least # of hydrogens

Front 15

dehydration- alcohol to ether

Back 15

-water removed from two alcohol molecules
-condensation rxn two molecules join
-h2so4 required, 140° required
-mainly for primary alcohols

Front 16

oxidation of alcohols

Back 16

- loss of two hydrogen's from hydroxy carbon
-oxidizing agents = k2cr2o7, KMnO4
-primary alcohols to an aldehyde to a carboxylic acid, important for energy production,
*breathalyzer test=
ch3ch2oh+cr2o7(orange)=ch3cooh+cr(green)
-oxidation of secondary alcohol to ketone
*lactic acid build up in muscle
-oxidation tertiary alcohols does not occur, no reaction

Front 17

ethers an anesthetics

Back 17

- induces insensitivity to pain
- Morton first to use ethyl ether
- inhalation anesthetic= highly volatile and flammable

Front 18

disulfide bonds

Back 18

thiols
-important in protein chemistry
- amino acid cysteine forms disulfide bonds
-maintains structure and confirmation of proteins
-heavy metal poisoning= hg and pb bonding interferes with protein or enzyme