in alcoholic beverages
used as a fuel
also called "grain alcohol"
toxicity: alcohol poisoning (decreased breathing, heart rate and gag reflex), long term use (bad for memory, liver and can cause addiction), and fetal alcohol syndrome in pregnant women
ethyl alcohol (ethanol)
cyclic ethers
the O of an ether contained in a ring
these compounds make good solvents because they are unreactive
one type is "Crown ethers" - form complexes with cations. phase transfer catalysts
flammable
oxidize in air to form unstable peroxides which leads to explosion hazard
unreactive towards acids, bases and oxidizing agents
can be halogenated
chemical properties of ethers
glycol = a diol in which 2 –OH groups are on adjacent Carbons
antifreeze & de-icers (depresses freezing and lowers freezing point)
Toxicity: etylene glycol is metabolized to oxalic acid (Forms calcium salt crystals in the kidneys which leads to renal failure)
ethylene Glycol (1,2-ethanediol) &
propylene Glycol (1,2-propanediol)
removal of H20 components that results in an alkene and water
can result in 2 different alkenes (major and minor determined by Zaitsev's rule)
this changes a single bond to a double bond (reverse of addition reaction)
only 2° and 3° alcohols can undergo this
requires an acid (H2SO4) and heat
dehydration / elimination reaction
rule that determines major and minor products in a dehydration reaction
most highly substituted alkene will predominate (alkene with most alkyl groups)
Zaitsev's rule
methyl alcohol (methanol)
the simplest alcohol
used to be used as fuel in race cars
used as a solvent for shellacs and varnishes
also called "wood alcohol"
toxic: can cause blindness and decrease pH pf blood
the O of an ether contained in a ring
these compounds make good solvents because they are unreactive
one type is "Crown ethers" - form complexes with cations. phase transfer catalysts
cyclic ethers
Low boiling point compared to alcohol – cannot form H-bonds
Disagreeable odor - methanethiol is added to natural gas to make leaks detectable
Oxidation Reactions – the product is a disulfide
Weak Acids – more acidic than phenols
properties of thiols
small alcohol (1-3 C) are soluble in water
4 C is partially soluble
5+ is completely insoluble
solubility of alcohol
KMnO4
K2Cr2O7
H2CrO4
oxidizing agents
isopropyl alcohol (2-propanol)
rubbing alcohol
used to cool the skin (decrease fever)
Toxicity: more toxic than ethanol, but causes fewer fatalities becaus bitter taste, causes vomiting
rubbing alcohol
used to cool the skin (decrease fever)
Toxicity: more toxic than ethanol, but causes fewer fatalities becaus bitter taste, causes vomiting
isopropyl alcohol (2-propanol)
organic compound where a sulfur atom is bonded to 2 carbon atoms by single bonds
Analogs of ethers
characteristic odors: garlic, onions
thioether
organic compound where a sulfhydryl group is bonded to a saturated C atom
sulfur analogs of alcohols
contain SH functional groups instead of OH
thiols
ethyl alcohol (ethanol)
in alcoholic beverages
used as a fuel
also called "grain alcohol"
toxicity: alcohol poisoning (decreased breathing, heart rate and gag reflex), long term use (bad for memory, liver and can cause addiction), and fetal alcohol syndrome in pregnant women
reaction with alcohol and HBr/HCl
nucleophile attacks carbon with the OH group (Br is better nucleophile than Cl)
Water is forced out
e.g. Lucas test reacts with 3° and 2° but not 1°
substitution
flammable (combustion reactions)
can't be dehydrated
doesn't react with mild oxidizing agents
substitution of OH with a halogen
weak acids
chemical properties of phenols
dehydration / elimination reaction
removal of H20 components that results in an alkene and water
can result in 2 different alkenes (major and minor determined by Zaitsev's rule)
this changes a single bond to a double bond (reverse of addition reaction)
only 2° and 3° alcohols can undergo this
requires an acid (H2SO4) and heat
Zaitsev's rule
rule that determines major and minor products in a dehydration reaction
most highly substituted alkene will predominate (alkene with most alkyl groups)
thiols
organic compound where a sulfhydryl group is bonded to a saturated C atom
sulfur analogs of alcohols
contain SH functional groups instead of OH
the simplest alcohol
used to be used as fuel in race cars
used as a solvent for shellacs and varnishes
also called "wood alcohol"
toxic: can cause blindness and decrease pH pf blood
methyl alcohol (methanol)
chemical properties of ethers
flammable
oxidize in air to form unstable peroxides which leads to explosion hazard
unreactive towards acids, bases and oxidizing agents
can be halogenated
a carbon atom that gains oxygen or loses hydrogen is oxidized
a carbon atom that loses oxygen or gains hydrogen is reduced
primary and secondary undergo this reaction, tertiary do not (because they do not have H attached to OH-bearing C
primary produce aldehyde and then carboxylic acid
secondary produce ketone
oxidation reaction
chemical properties of phenols
flammable (combustion reactions)
can't be dehydrated
doesn't react with mild oxidizing agents
substitution of OH with a halogen
weak acids
Glycerol (1, 2,3-propanetriol)
lubricant
used in lotions, soaps, shaving cream, etc.
“biological antifreeze” - some insects have this in blood to decrease freezing point
a normal product of fat metabolism - triglycerides
thioether
organic compound where a sulfur atom is bonded to 2 carbon atoms by single bonds
Analogs of ethers
characteristic odors: garlic, onions
low melting solids or oily liquids at room temp
most are not very soluble in water
colorless, volitile solid
mildly acidic and can cause bad chemical burns
vapors of these are bad for eyes / respiratory tract
used as antimicrobial/antiseptic to kill germs
physical properties of phenols
condensation
removal of H2O (water is liberated)
2 molecules combine to form a larger one
only 1° alcohols undergo this
product is an ether
common alcohols are liquid at room temp
boiling point increases as the length of carbon chain increases (due to increased intermolecular forces that require more heat to pull them apart)
alcohols with more than one OH group have significantly higher boiling points
boiling point of alcohol
