Organic I -335 Section 02
Chapter 10 Alcohols
Italian Grappa 40 to 60 % alcohol (ethanol)
Properties
(10.1) Structure and nomenclature of alcohols
(10.2) Physical properties of alcohols
(10.3) Acidity and basicity of alcohols
Reactions
(10.4) Reaction of alcohols with active metals
(10.5) Conversion of alcohols to haloalkanes and
sulfonates
Grappa is made by fermentation and steam (10.6) Acid-catalyzed dehydration of alcohols
distillation of grape pomace (vinaccia, the important
stems, skin, and seeds leftover from wine (10.7) The pinacol rearrangement
making ) this produces a small amount (10.8) Oxidation of alcohols important
of methanol, the result of enzymatic
(10.9) Thiols (will do little)
hydrolysis of pectin present in pomace.
When making grappa, the methanol, b.p. CH3OH
65°C, must be carefully distilled (head cut )
from the alcohol , b.p. 78 °C , containing CH3OH
fractions (heart) and the remaining pectin 1
heavier pulp (tail )
,Properties
(10.1) Structure and nomenclature of alcohols
(10.2) Physical properties of alcohols
(10.3) Acidity and basicity of alcohols
Reactions
(10.4) Reaction of alcohols with active metals
(10.5) Conversion of alcohols to haloalkanes and sulfonates
(10.6) Acid-catalyzed dehydration of alcohols important
(10.7) The pinacol rearrangement
(10.8) Oxidation of alcohols important
(10.9) Thiols (will do little)
2
,.. A single C, but a big
difference!!
Ethanol (ethyl alcohol, grain alcohol): CH3CH2OH
• Produced commercially from ethylene and through biological (yeast)
fermentation of carbohydrates
• Useful as a solvent, industrial starting material, fuel , and found in
alcoholic beverages
methanol CH3OH
• Useful as a solvent, paint remover, and industrial starting material
• HIGHLY toxic if ingested or absorbed or inhaled (blindness & death )
• Metabolized by alcohol dehydrogenase as formaldehyde , formic acid.
Toxic. Antidote is Fomepizole, (IUPAC: 4-methylpyrazole) but if
nothing else available? Ethanol (competitive inhibition )
3
, .. Small changes , but a big
difference!!
• 2-Propanol (isopropyl alcohol or isopropanol)
main component of rubbing alcohol, …and
some hand sanitizers!!
• Butanol solvent, some hydraulic fluids
• 1,2,3-Propanetriol (glycerol or glycerin)
nontoxic, sweet tasting, is used as a food
moistening agent (tobacco humidors, hand
creams) and for its soothing qualities (soaps).
• 1,2-ethanediol (ethylene glycol)
Antifreeze … sweet tasting.. And TOXIC!!
4
Chapter 10 Alcohols
Italian Grappa 40 to 60 % alcohol (ethanol)
Properties
(10.1) Structure and nomenclature of alcohols
(10.2) Physical properties of alcohols
(10.3) Acidity and basicity of alcohols
Reactions
(10.4) Reaction of alcohols with active metals
(10.5) Conversion of alcohols to haloalkanes and
sulfonates
Grappa is made by fermentation and steam (10.6) Acid-catalyzed dehydration of alcohols
distillation of grape pomace (vinaccia, the important
stems, skin, and seeds leftover from wine (10.7) The pinacol rearrangement
making ) this produces a small amount (10.8) Oxidation of alcohols important
of methanol, the result of enzymatic
(10.9) Thiols (will do little)
hydrolysis of pectin present in pomace.
When making grappa, the methanol, b.p. CH3OH
65°C, must be carefully distilled (head cut )
from the alcohol , b.p. 78 °C , containing CH3OH
fractions (heart) and the remaining pectin 1
heavier pulp (tail )
,Properties
(10.1) Structure and nomenclature of alcohols
(10.2) Physical properties of alcohols
(10.3) Acidity and basicity of alcohols
Reactions
(10.4) Reaction of alcohols with active metals
(10.5) Conversion of alcohols to haloalkanes and sulfonates
(10.6) Acid-catalyzed dehydration of alcohols important
(10.7) The pinacol rearrangement
(10.8) Oxidation of alcohols important
(10.9) Thiols (will do little)
2
,.. A single C, but a big
difference!!
Ethanol (ethyl alcohol, grain alcohol): CH3CH2OH
• Produced commercially from ethylene and through biological (yeast)
fermentation of carbohydrates
• Useful as a solvent, industrial starting material, fuel , and found in
alcoholic beverages
methanol CH3OH
• Useful as a solvent, paint remover, and industrial starting material
• HIGHLY toxic if ingested or absorbed or inhaled (blindness & death )
• Metabolized by alcohol dehydrogenase as formaldehyde , formic acid.
Toxic. Antidote is Fomepizole, (IUPAC: 4-methylpyrazole) but if
nothing else available? Ethanol (competitive inhibition )
3
, .. Small changes , but a big
difference!!
• 2-Propanol (isopropyl alcohol or isopropanol)
main component of rubbing alcohol, …and
some hand sanitizers!!
• Butanol solvent, some hydraulic fluids
• 1,2,3-Propanetriol (glycerol or glycerin)
nontoxic, sweet tasting, is used as a food
moistening agent (tobacco humidors, hand
creams) and for its soothing qualities (soaps).
• 1,2-ethanediol (ethylene glycol)
Antifreeze … sweet tasting.. And TOXIC!!
4
