School Science Lessons
Please send comments to: J.Elfick@uq.edu.au 16 Organic chemistry, tests for organic compounds
Table of contents 220.127.116.11 Acetal 18.104.22.168 Acetates (ethanoates) 22.214.171.124 Acetylene, C2H2,
ethyne 126.96.36.199 Acid anhydrides 188.8.131.52 Acyl halides 184.108.40.206.1 Acrylamide 220.127.116.11 Acyclic hydrocarbons 16.1.01 Addition reactions 18.104.22.168 Alcohols, phenols, thiols 3.8.0 Alcohols, Fatty alcohols, lauryl
alcohol 22.214.171.124a Alcohol, Ethanol safety 126.96.36.199 Aldehydes 188.8.131.52 Alkaloids from plants 184.108.40.206 Alkanes (CnH2n+2),
paraffins 220.127.116.11 Alkenes (CnH2n),
olefins 18.104.22.168 Alkynes (CnH2n-2),
acetylenes 22.214.171.124 Amides 126.96.36.199.00 Amines 188.8.131.52 Arenes, benzene 184.108.40.206 Benzoyl group Bisphenol-A (BPA), Epoxy resin
polymer 220.127.116.11a Carbamates 18.104.22.168 Carbides 22.214.171.124 Carboxylic acids and fatty
acids 16.4.1.01 Carbonyls Carvacrol, C10H14O 18.7.23 Chloramines in swimming pools 126.96.36.199.05 Clenbuterol, C12H18Cl2N2O 16.2.10 Coal tar products,
creosote 188.8.131.52.1 Cyanamides, inorganic (CN22-), 184.108.40.206 Cyanocrylates, "Superglue" 16.14.0 Dioxins, "Agent orange",
PCBs 9.10.0 EDTA, ethylenediaminetetraacetic
acid 16.6.1 Essential oils, volatile oils,
ethereal oils 16.5.0 Esters, derivatives of fatty
acids 220.127.116.11 Ethane (C2H6) 18.104.22.168 Ethers, group: (-O-), in organic compound 22.214.171.124 Ethyl cellulose 126.96.36.199 Epoxy resin polymers 188.8.131.52.1 Ethylenediamine 16.6.2 Fixed oils, non-volatile oils 184.108.40.206 Fluorescent liquids 16.1.12 Fractional distillation of crude oil 220.127.116.11 Imides, imido group: (-CONHCO-) 18.104.22.168a Imines, imino group: -NH-, or =NH 22.214.171.124b Cyclic imines Methane, natural gas 126.96.36.199 Methyl bromide, bromoethane,
CH3Br 188.8.131.52.01 Methylamine ionization reaction 16.2.4 Nitrogen compounds, one atom of nitrogen 184.108.40.206 Nitrogen compounds, two or more nitrogen
atoms 220.127.116.11.03 Nitrosamines 18.104.22.168.04 Nitramine (acid-base indicator) 22.214.171.124 Nitriles 126.96.36.199 Nitrites (NO2-) 188.8.131.52 Nitroalkanes (nitroparaffins) 16.1.0 Organic chemistry 16.2.3 Organometal compounds 16.1.03 Oxidation reactions, loss of electrons 184.108.40.206 Oximes (hydrox-imino-alkanes) (C:NOH) 16.2.6 Phosphorous compounds 3.32.0 Prepare gases, gas generation
apparatus 16.1.00 Prepare organic compounds 220.127.116.11.02 Prepare phenylamine 18.104.22.168 Quinones 16.1.04 Reduction reactions, gain of electrons Ribose, C5H10O5 Ribulose, C5H10O 22.214.171.124 Salts, organic salts, sodium ethanoate 126.96.36.199 Saturated hydrocarbons, hexane, C6H14 188.8.131.52 Sulfur organic compounds 184.108.40.206 Tests for organic compounds 16.6.3 Vegetable oils, Plant oils 220.127.116.11 Acyclic hydrocarbons 18.104.22.168 Acyclic hydrocarbons, alkanes, alkenes 22.214.171.124 Alkanes (CnH2n+2),
paraffins 126.96.36.199 Arenes, benzene (C6H6) 188.8.131.52 Butane (C4H10) 184.108.40.206 Prepare butane 220.127.116.11 Combustion of butane 18.104.22.168 Cycloalkanes 22.214.171.124 Ethane (C2H6) 126.96.36.199 Prepare ethane gas 188.8.131.52 Hexane (C6H14) 184.108.40.206 Heptane (C7H16) LPG (Liquefied Petroleum Gas, LP gas) Methane, natural gas 220.127.116.11 Octane (C8H18),
Octane number 18.104.22.168 Octadecan-1-ol (C18H38O) 22.214.171.124 Octanol, [CH3(CH2)7OH] 126.96.36.199 Pentane (C5H12) 188.8.131.52 Propane (C3H8) 184.108.40.206 Alkanes (CnH2n+2),
Alkanes, cyclohexane, heptane, hexane, liquefied petroleum gas (LPG),
octane, pentane, petroleum spirit
Alkanes: methane, ethane, propane, butane, pentane, hexane, heptane,
octane, nonane. 220.127.116.11 Alkanes (CnH2n+2),
Alkanes, skeletal formula: See diagram 16.1.1 18.104.22.168a Alkanoic acids, RCOOH, -oic acids 22.214.171.124 Acyclic hydrocarbons, alkanes, alkenes,
alkynes Iodine value 3.29.0 Collect and weigh the gaseous
products of a burning candle 126.96.36.199 Friedel-Crafts reaction 188.8.131.52 Nitroalkanes (nitroparaffins),
(CnH2n+1NO2) 184.108.40.206 Oximes (hydrox-imino-alkanes),
Group: (C:NOH) 220.127.116.11 Petroleum gas (See 18.104.22.168
to 22.214.171.124) 126.96.36.199 Tests for unsaturated alkanes (Experiments) 188.8.131.52 Alkenes (CnH2n),
184.108.40.206.0 Alkenes (CnH2n), olefins 220.127.116.11.1 Prepare ethene (ethylene), C2H4 18.104.22.168.2 Dienes, diolefins 22.214.171.124 Arenes, benzene 126.96.36.199 Arenes, benzene 188.8.131.52.1 Phthalic acid 184.108.40.206 Friedel-Crafts reaction 220.127.116.11 Nitration (Experiment) 18.104.22.168 Alcohols, phenols,
Alcohols, R-OH, -OH hydroxyl, Prefix: hydroxy-, Suffix: -ol (-OH: alcohol),
(alkanol, alkyl alcohol) 6.6.18 Alcoholic fermentation,
yeast Saccharomyces cerevisiae (Exp.) 22.214.171.124 Alcohols 126.96.36.199.1 Alcohols, primary, secondary
and tertiary aliphatic alcohols 188.8.131.52.1a Tests for alcohols, potassium manganate
(VII) 16.1.3b Butanol (C4H9OH) 16.1.3c Butyl glycol (C4H9OCH2CH2OH) 16.1.0 Carbolic acid, phenol,
TCP, Dettol 184.108.40.206.3 Cresols 220.127.116.11.1 Dihydric alcohols, glycol 16.5.0 Ethanol 1.4 List of alcohols 16.5.1 Methylated spirits 18.104.22.168.2 Naphthols 22.214.171.124.3 Nitroglycerine (UK),
nitroglycerin (USA) 126.96.36.199.4 Nitrocellulose, gun cotton 12.12.4 Oxidation of glycerol by potassium
permanganate 188.8.131.52 Phenols 184.108.40.206 Polyhydric alcohols 4.3.8 Prepare alcohol using immobilized
yeast cells (Exp.) 220.127.116.11.2 Prepare sodium ethoxide 16.1.3a Propanol (C3H7OH) 18.104.22.168a Pyrogallol 22.214.171.124.4 Resorcinol 16.1 3.2.5 Triclosan, organohalogens 126.96.36.199.2 Trihydric alcohols, glycerol 188.8.131.52 Thiols (mercaptans) 16.1.13 Prepare triodomethane,
(iodoform) 16.1.14 Prepare trichloromethane gas (chloroform) 184.108.40.206 Reaction of acetone with bleaching
powder 220.127.116.11 Reaction of ethyl alcohol with bleaching
powder 18.104.22.168 Carbides 22.214.171.124 Carbides Methanides, aluminium carbide, Al4C3 Acetylides, calcium carbide CaC2 Sesquicarbides, e.g. Mg2C3 Covalent carbides, boron carbide, carborundum Silicon carbides (Carborundum) 16.1.12 Fractional distillation
of crude oil
16.1.12 Fractional distillation of crude oil Asphalt Hydraulic fluid Mineral oil 126.96.36.199 Petroleum gas (methane, ethane, propane,
butane), LPG 188.8.131.52 Naphtha (ligroin), processed to make
gasoline 184.108.40.206 Petrol, "gas", gasoline, motor fuel 220.127.116.11 Kerosene, kerosine, paraffin oil,
jet engine fuel, tractor fuel 18.104.22.168 Diesel oil, gas oil or diesel distillate,
diesel fuel, heating oil 22.214.171.124 Lubricating oil, motor oil, grease 126.96.36.199 Paraffin wax, heavy gas, fuel oil 188.8.131.52 Residuals, bitumen, "tar", asphalt,
waxes, petroleum jelly 184.108.40.206 Nitrogen compounds,
two or more nitrogen atoms 220.127.116.11 Azide compounds 18.104.22.168 Azo compounds 22.214.171.124 Diazo compounds 126.96.36.199 Sulfur organic
Sulfur compounds (For the "thio" prefix, replace oxygen by sulfur, e.g.
thiobenzamide [PhC(=S)NH2]) 188.8.131.52 Isothiocyanates 184.108.40.206 Sulfides Sulfonic acids, group: R-SO2OH,
e.g. methanesulfonic acid, CH3SO2OH, Salts or esters:
sulfonates 220.127.116.11 Sulfonium compounds 18.104.22.168 Thiocyanates 22.214.171.124 Silicones: polymeric
unbranched siloxanes, formula (-OSiR2-)n (R not equal
to H) 126.96.36.199 Siloxanes 188.8.131.52 Sulfoxide 184.108.40.206 Thiols (mercaptans) 220.127.116.11.2 Allyl mercaptan 18.104.22.168a Methanethiol from asparagus 22.214.171.124.1 Methyl mercaptan 126.96.36.199.3 Ethyl mercaptan, ethanethiol, CH3CH2SH 188.8.131.52.4 Thiophene, thiolane, THT (CH2)4S 184.108.40.206.5 Phenothiazine, PTZ, C12H9NS 16.1.0 Organic chemistry,
Carbon, C See diagram 16.0.0: Organic chemistry functional
groups See diagram 16.0.1: Tetrahedral geometry of
carbon, methane molecule, isobutyl alcohol
Organic chemistry is the chemistry of carbon compounds.
Hydrocarbons contain carbon and hydrogen only.
The main types are the alkanes, alkenes and alkynes.
In alkenes and alkynes, addition reactions occur at the double bonds =
or triple bonds.
Triple bond (has 6 electrons in the bond), e.g. Carbon monoxide, C≡O
When heating organic chemicals, do not point the test-tube towards anyone!
Organic compounds may suddenly vaporize and spurt out of the test-tube!
1. Classification by molecular framework
1.1 Acyclic compounds have chains of unbranched or branched carbon atoms
1.2 Carbocyclic compounds have rings of carbon atoms
1.3 Heterocyclic compounds have rings of carbon atoms with one atom in
a ring not carbon, e.g. O, N, S
2. Classification by functional group, e.g. hydroxyl group, OH, is characteristic
of alcohols 16.1.00 Prepare organic compounds 16.1.01 Addition reactions 16.1.02 Substitution reactions (displacement reactions) 16.1.03 Oxidation reactions, loss of electrons 16.1.04 Reduction reactions, gain of electrons 16.1.01 Addition reactions
Atoms are added to the two atoms of a double bond or triple bond in an
unsaturated compound, also when no atoms are replaced,
but extra covalent bonds are formed.
Alkenes (olefins) or alkynes (acetylenes) --> haloalkanes (alkyl halides),
or primary alkanols (alcohols), or secondary alkanols, (alcohols)
Example: HCl + CH2CH2 --> CH3CH2Cl 16.1.02 Substitution reactions,
Replacement of an atom or group in a molecule by another atom or group
Alkanes (paraffins) --> haloalkanes (alkyl halides) --> amines
Haloalkanes (alkyl halides) <--> primary alkanols (alcohols), (-CH2-OH)
Alkanoic acids --> esters --> amides
Example: CH4 + Cl2 --> CH3Cl + HCl
[chlorination produces chloromethane (methyl chloride) and HCl.] 16.1.03 Oxidation reactions,
loss of electrons
Primary alcohols can be directly oxidized to aldehydes or carboxylic acids
Primary alkanols (alcohols) (-CH2-OH) --> alkanals (aliphatic
Example: CH3OH + O2 --> CH2O + H2
(Pt catalyst) [Oxidation of methanol to methanal using a platinum catalyst]
Alkanals --> alkanoic acids, e.g. butanoic acid, CH3(CH2)2COOH
Secondary alkanols (alcohols) (CH3)2CHOH -->
alkanones Alkanones (ketones, RCOR'), simplest ketone:
acetone (2-propanone, dimethyl ketone), O=C(CH3)2 16.1.04 Reduction reactions,
gain of electrons 9.142 Fehling's test
Alkanals (aliphatic aldehydes) --> primary alkanols (alcohols), (-CH2-OH)
Add drops of formalin to a test-tube one quarter filled with Fehling's
A and B solutions and heat to boiling.
Note the yellow then orange then red precipitate of copper (I) oxide.
The copper from the copper (II) sulfate solution has been reduced from
copper (II) to copper (I). 220.127.116.11 Acyclic hydrocarbons,
alkanes, alkenes, alkynes
| See diagram 16.1.1: Alkanes, alkenes, alkynes
| See 10.6.3: Distil crude oil and collect
Alkanes, alkenes, alkynes or their derivatives are aliphatic compounds,
i.e. non-cyclic organic compounds.
Acyclic molecules have carbon atoms in chains but not in rings.
The chains may be unbranched or branched.
Aromatic compounds contain a benzene ring in the molecule.
Hydrocarbon compounds contain only hydrogen and carbon.
Hydrocarbons are usually colourless and have low solubility in water.
Crude oil is a mixture of hydrocarbons.
Hydrocarbons may be saturated, i.e. have only single bonds, or unsaturated,
i.e. contain multiple bonds, e.g. double bond =, or triple
bond, carbon monoxide, C≡O. Iodine value is the number of grams of iodine
absorbed by 100 g of fat or oil, to indicate the amount of unsaturated
acids. 18.104.22.168 Alkanes (CnH2n+2),
The first 10 unbranched alkanes and molecular formula: methane (CH4),
ethane (C2H6), propane (CH3H8),
pentane (CH5H12), hexane (CH6H14),
heptane (CH7H16), octane (CH8H18),
nonane (CH9H20), decane (CH10H22).
Alkanes burn in oxygen to give carbon dioxide and water.
Candle wax is a mixture of different alkanes that are solid at room temperature.
Alkanes are usually associated with natural petroleum deposits and can
be distilled from petroleum.
1. Alkanes (paraffins) are saturated hydrocarbons, i.e. all single bonds
between C atoms, have formula CnH2n+2
and names end in "ane".
The names of unbranched alkanes come from the number of carbon atoms.
The name of branched alkanes come from the longest chain of carbon atoms.
The hydrocarbon branches, alkyl groups, symbol R, are formed by removing
one hydrogen atom from the alkane and named by
changing the "ane" to "yl", e.g. methane, CH4 to methyl, CH3-,
The carbon atoms of the longest continuous name are numbered starting
at the end of the chain closest to the first branch, e.g. an
eight carbon chain with an ethyl group attached to carbon 5 and a methyl
group attached to carbon 3 and carbon 4 is called
Saturated hydrocarbons, e.g. hexane, C6H14, all
carbons have either four or three hydrogens bonded to them and no double
triple bonds or rings, react in almost the same way. 2. Formation of alkanes
2.1 Hydrogenation of alkenes --> alkanes
CH2=CH2 + H2 --> CH3-CH3
ethylene + hydrogen --> ethane
CH3CH=CHCH3 + H2 --> CH3CH2CH2CH3
2.2 Decarboxylation (remove CO2) from molecules that have -
RCOONa + NaOH --> R-H + Na2CO3 (dry distillation
with soda lime)
CH3COONa + NaOH --> CH4 + Na2CO3 22.214.171.124a Alkanoic acids,
RCOOH, -oic acids Butanoic acid, C3H7COOH,
butyric acid Ethanoic acid, CH3COOH,
acetic acid, vinegar
Methanoic acid, HCOOH, formic acid: 126.96.36.199.3 Propanoic acid, propionic
Isobutyric acid, 188.8.131.52.6 184.108.40.206 Cycloalkanes
Cycloalkanes, CnH2n, cycloolefins, cyclanes, polymethylenes,
cycloparaffins, saturated carbon rings.
Cycloalkanes are saturated hydrocarbons with a ring of carbon atoms,
e.g. The position of branches depends on the alphabetical order of the
branch names so that highest in order is attached to carbon 1,
Cyclopropane, C3H6, colourless gas, former anaesthetic,
petroleum odour, easily ignited, may cause frostbite, containers may explode
Cyclobutane, C4H8, tetramethylene, condenses to liquid
at 13oC, insoluble in water, containers may explode
Cyclopentane, C5H10, pentametylene, colourless liquid,
flash point -37oC, insoluble in water Cyclohexane, C6H12,
Cycloheptane C7H14, heptamethylene, colourless oily
liquid, flash point 16oC, narcotic effect
Cyclooctane C8H16, octamethylene 220.127.116.11 Arenes, benzene See 18.104.22.168: Aromatics, aromatic
compounds, benzene derivatives, arenes See diagram 16.8.1: Benzene compounds Benzene, C6H6,
has a stable six-sided ring structure.
Arenes, e.g. benzene, naphthalene, anthracene, phenanthrene.
Arenes do not mix with water, but they do mix with hydrocarbons and all
Arenes usually burn with a smoky flame, as do most aromatic compounds,
because of the high carbon: nitrogen ratio.
So when they burn in air, some carbon soot usually remains in the air.
Arenes are called aromatic compounds because the first arenes were isolated
from fragrant oils.
However, nowadays aromatic refers to the structure not the smell. 22.214.171.124.1 Phthalic acid
Phthalic acid, C8H6O4, benzene-1, 2-dicarboxylic
acid, formerly derived from naphthalene.
Phthalic anhydride, benzene-1, 2-dicarboxylic anhydride, phthalandione,
Toxic, strong skin irritant
Phthalic anhydride, C8H4O3, used to produce
phthalic esters, chemical plasticisers, plastics from vinyl chloride. 3.0.4 Phthalates 126.96.36.199 Nitration See 10.01.10: Liebig condenser
Substitution of a -NO2 group for a hydrogen atom in an arene
ring, e.g. bromine.
The reaction substitutes a hydrogen atom in an arene ring by a -NO2
Heat benzene with a mixture of nitric and sulfuric acid catalyst in a
Liebig condenser at 330 K.
benzene + HNO3 --> benzene-NO2 + H2O
benzene + NO2+ --> benzene-NO2 + H+
Also, some 1.3-dinitrobenzene may form. 188.8.131.52 Friedel-Crafts
The reaction substitutes a hydrogen atom in an arene ring of a halogen
alkane by an organic group, R, using aluminium chloride catalyst.
RCl + AlCl3 --> R+ + AlCl4-
For example, benzene with chloromethane forms methyl benzene.
benzene + CH3+ --> benzene-CH3 + H+
CH3Cl +AlCl3 --> CH3+ +
AlCl4- 184.108.40.206 Tests for unsaturated
1. Ignition tests for unsaturation
Ignite a substance in an evaporating basin and observe the smoke over
The darker or more sooty the smoke, the more unsaturated, e.g. aromatic
If clear over a luminous flame the compound is saturated, e.g. n-hexane. 2. Bromine tests for unsaturation.
Bromine is a coloured compound but it reacts with double bonds or triple
bonds to form a colourless brominated compound.
alkene or alkyne + bromine water, yellowish colour disappears. 3. Decolorization of bromine water.
Hexane does not decolorize bromine water.
Aromatic compounds also do not decolorize bromine water because they are
stable compounds. 4. Baeyer test
Change in colour of the reagent (purple permanganate to brown manganese
dioxide), redox reaction
Brominate hexane and other saturated hydrocarbons with the right wavelength
of light and shining it on the reaction vessel, or adding
peroxide or by heating the reaction. 220.127.116.11 Ethane (C2H6)
| See 3.32.0: Prepare gases with a gas
generation apparatus, Collect insoluble gases over water.
| See diagram 16.1.1: Ethane
Ethane is a colourless and odourless gas, which has properties similar
to methane. 18.104.22.168 Prepare ethane
This experiment was called the "wet asbestos method" because asbestos wool,
was used to soak up methyl iodide in the test-tube.
However, asbestos wool is not allowed in schools.
Pour 2 cm methyl iodide in a test-tube.
Add 5 g of copper turnings and push it down firmly with a spatula.
Set up the apparatus and heat the mixture.
2CH3I + 2Cu --> C2H6 + Cu2I2 22.214.171.124 Propane (C3H8)
Colourless liquefied petroleum gas, a bottled gas, b.p. -42.2oC,
catalytic cracking forms propylene, propellant, aerator, fuel for gas
barbecue and blow torch 126.96.36.199 LPG (Liquefied
Petroleum Gas, LP gas)
LPG is a clean burning fuel and is stored in gas cylinders as bottled
LPG is a simple asphyxiant.
It consists of propane (about 95%) together with varying proportions of
butane, propylene and butylene.
A bad smelling compound is added so that the presence of the gas can be
Incomplete combustion forms carbon monoxide.
Do not search for a gas leak with a lighted match or lighted taper, but
use a soap solution. 188.8.131.52 Butane (C4H10)
| See diagram 3.32: Collect insoluble gases over
water, See 3.
| See diagram 16.1.2: Butane isomers
n-Butane, b.p. -0.5oC, relative density 0.60 at 0oC,
is stored as liquid under pressure in steel cylinders giving
Calor gas and cigarette lighter gas. (in cigarette lighters and portable
Butane is a Highly flammable gas at room temperature, vapour pressure 2.4
Butane gas is stored as liquid under pressure in fire lighters.
If lighter trigger is squeezed, canister opens and liquid forms a vapour.
Cigarette lighter fuel is 90% butane, isomer isobutane.
Sudden decompression in aircraft can cause butane cannisters to rupture. 184.108.40.206 Prepare butane
This experiment was called the "wet asbestos method" because asbestos
wool was used to soak up the ethyl iodide in the test-tube.
However, asbestos wool is not allowed in schools.
Pour 2 cm ethyl iodide in a test-tube.
Add 5 g of copper turnings and push it down firmly with a spatula.
Set up the gas generation apparatus and heat the mixture.
2C2H5I + 2Cu --> C4H10
+ Cu2I2 220.127.116.11 Combustion of butane
Butane / Oxygen combustion
2C4H10 + 13O2 --> 8CO2
+ 10H2O + energy 18.104.22.168 Pentane (C5H12)
Pentane, b.p. 36.3oC, relative density 0.63, is made by distillation
of petroleum. 22.214.171.124 Hexane (C6H14)
Hexane, b.p. 68.7oC, relative density 0.66, exists as five
compounds with same formula, normal hexane, n-hexane, in petrol and
petroleum ether solvent, colourless liquid ethereal odour.
"Shellite" (Australia) is 60% hexane and 40% heptane. 126.96.36.199 Heptane (C7H16)
Heptane, b.p. 98oC, relative density 0.68, nine isomers, normal
heptane has similar properties to normal hexane. 188.8.131.52 Octane (C8H18),
Octane number See diagram 16.1.1h: Octane ratings
Octane, b.p. 126oC, relative density 0.702 at 20oC,
exists as eighteen compounds, in petroleum.
Isomeric with iso-octane, 2, 2, 4-trimethylpentane (CH3)3CCH2CH(CH3)2.
Octane number See: 184.108.40.206: Spark plugs, pre-ignition
Some hydrocarbons with unbranched carbon chains prematurely explode in
the cylinder and produce an audible knocking sound or
"ping" sound (knocking, pinking).
A scale of "knock property" has isooctane (2, 2, 4-trimethylpentane) at
100 (a good fuel) and heptane at 0 (a poor fuel).
So gasoline with octane number 80 has the same properties as a mixture
of 80% isooctane and 29% heptane.
Octane number is the percentage of iso-octane normal heptane mix with
the same knocking behaviour of the fuel being tested, so it
indicates the knock rating of a motor fuel.
A high octane fuel has a longer self-ignition delay in motor car engine.
In Brisbane, most " family cars" use 91 octane "unleaded petrol".
This is the lowest octane rating of the different petrol sold in garages.
A high octane rating of a fuel means that it has less tendency to pre-ignite
in a high compression engine.
Pre-ignition means that before the spark plug has fired, the fuel air mixture
burns because of heat created in the cylinder by compression.
Unleaded petrol has the octane rating 98.
Engine compression ratio
Octane number to be knock-free
Octadecan-1-ol, C18H38O, octadecyl alcohol, 1-octadecanol,
Use octadecan-1-ol for melting point curve experiments. 220.127.116.11, Octanol, CH3(CH2)7OH
Octanol, CH3(CH2)7OH, 1-octanol, octyl
alcohol, n-octyl alcohol, octan-1-ol, caprylic alcohol, Flammable 3.10.0 Poisons and First Aid: See Octanol 18.104.22.168.0 Alkenes (CnH2n),
Alkene, R1R2C=CR3R4 (double
CC bond =), Prefix: alkenyl-, Suffix: -ene (no principal functional group)
Alkene (olefins, olefines), CnH2n, e.g. ethylene,
ethene C2H4, ethene (ethylene) (H2C=CH2),
amylene, propadiene (allene)
(R2C=C=CR2), dienes buta-1.2-diene, (CH3CH=C=CH2),
amylene See diagram 16.1.1: Cyclodienes, cis-trans
1. Suffix: -ene for C=C (olefin, olefins, olefines) are unsaturated hydrocarbons
with at least one double bond between C atoms, C=C.
Alkenes have the formula CnH2n.
Alkenes include ethene (ethylene, C2H4, CH2=CH2),
ethenyl (vinyl CH2=CH-), 3-propenyl (allyl, CH2=CH-CH2-),
e.g. vinyl chloride
(chlorethene, CH2CHCl), allyl chloride (3-chloropropene CH2=CH-CH2Cl).
(In the textile trade "olefin" refers to synthetic fibre, polyolefin fibre,
that are long-chain polymers of ethylene or propylene,
i.e. polyethylene (polypropylene, PP).
Alkenes decolorize acidified potassium permanganate solution and bromine
2. The cycloalkenes, cycloolefins, are closed chain, non-aromatic forms,
e.g. cyclopropene, CH.CH.CH2, cyclobutene, cyclopentene,
cyclohexene. 22.214.171.124.1 Prepare ethene
(ethylene), C2H4 See 3.32.0: Prepare gases with a gas
The preparation is an example of the dehydration of an alcohol.
1. Slowly add 10 mL of concentrated sulfuric acid to 5 mL of ethanol and
1 g of powdered aluminium sulfate in the gas preparation
Pass the gas formed through sodium hydroxide solution to remove sulfur dioxide
and carbon dioxide!
Collect the gas over water.
Heat only if necessary.
Pass the gas through sulfuric acid as dehydrating agent.
CH3CH2OH --> H2C=CH2 + H2O 2. Add 3 mL ethanol to a plug of glass wool in
a boiling tube.
Glass wool is not recommended for use in school laboratories.
Cover the glass wool with porous pot and heat the porous pot.
C2H5OH --> C2H4 (g) + H2O 3. This experiment was called the "wet asbestos
method" because asbestos wool was used to soak up the ethyl iodide in the
However, asbestos wool is not allowed in schools.
Pour 2 cm methyl iodide in a test-tube.
Add 5 g of copper turnings and push it down firmly with a spatula.
Set up the apparatus and heat the mixture.
2CH3I + 2Cu --> C2H6 + Cu2I2 4. Prepare ethene with ethanol, method 1. See 3.96: Breakdown ethanol to ethene
Put some cleaned and dried unglazed porcelain chips in a flask.
Add 10 mL of pure ethanol (absolute alcohol).
Slowly pour 30 mL of concentrated sulfuric acid down the sides of the
flask. Be careful! Shake the flask gently under cool water to avoid alcohol being carbonized
because of increase in temperature.
Fit the flask with a thermometer and a delivery tube inserted in a two-holes
Heat the flask to raise the temperature quickly to 170oC,
then control at 170oC.
This heating procedure is used to increase the use ratio of ethanol and
Wait until exclusion of the air in the flask and then collect the produced
ethene gas over water.
Concentrated sulfuric acid and sodium hydroxide solution can be used to
absorb and remove the small quantities of the ethyl ether
(sulfuric ether) vapour, carbon dioxide and sulfur dioxide present in the
C2H5OH (l) -> C2H4 (g)
+ H2O at 170oC. 5. Prepare ethene with ethanol, method 2. See diagram 16.10.3: Prepare ethene
Absorb ethanol in cotton wool and push this to the bottom of a hard glass
Pack small pieces of unglazed porcelain in the middle of the test-tube.
Fit a delivery tube to collect ethene gas over water.
First heat the porous pot strongly and then heat gently the cotton wool
to produce some ethanol vapour.
This vapour breaks down over the hot porous pot to produce ethene gas
and water vapour.
The temperature should be above 170oC otherwise the reaction
produces dimethyl ether.
Collect the ethene over water.
Be careful! Disconnect the delivery tube when heating stops to avoid a
suck back of water onto the hot porous pot. 126.96.36.199.2 Dienes, diolefins
1. Dienes are alkenes with two C double bonds in the molecule, CnH2n-2,
(same formula as alkynes, so dienes are alkyne isomers).
2. Cumulated dienes have two C double bonds next to each other, e.g. 1,
3. Conjugated dienes have two double bonds separated by a single bond,
e.g. (buta-1, 3-diene) (CH2=CH-CH=CH2) and
(1, 3-pentadiene) (H2C=CH-CH=CH-CH3).
4. Unconjugated dienes, have two double bonds separated by two or more
5. Cyclodienes, 1.3-cyclohexadiene, 1.4-cyclohexadiene 188.8.131.52.3 Trienes
Trienes have three C double bonds in the molecule, CnH2n-4,
e.g. C6H8 (1, 3, 5-hexatriene) Menthatriene, C10H14,
(1, 3, 8-p-menthatriene) (para-menthatriene), terpene, camphor, woody aroma
and taste, not used for
fragrances of flavours, colourless-yellow liquid, roasted odour, not used
for fragrances of flavours, parsley aroma | in Parsley | Jesuit's tea | 184.108.40.206 Alkynes (CnH2n-2),
Alkyne, R1-CC-R2 (triple CC bond involves 6 electrons, e.g. acetylene,
Alkyne, Prefix: alkynl-, Suffix: -yne (no principal functional group),
1. acetylenes: ethyne (acetylene) (C2H2 (HCCH),
Suffix: (-yne), for (CC) (acetylenes), are unsaturated hydrocarbons with
at least one triple bond (), between C atoms, include ethyne
(C2H2), acetylene (HCCH), 3-propargyl (propargyl),
Alkynes decolorize acidified potassium permanganate solution and bromine
2. The cycloalkynes are closed chain, non-aromatic forms, e.g. cyclooctyne,
C8H12 (the smallest form). 220.127.116.11.0
Acetylene, C2H2, ethyne 18.104.22.168.1 Prepare
acetylene 22.214.171.124.2 Tests for
acetylene 126.96.36.199 Tests for gases from
burning hydrocarbons, oxyacetylene welding 188.8.131.52 Oxyacetylene welding 184.108.40.206 Alcohols See diagram 16.0.1: Tetrahedral geometry of
carbon, methane molecule, isobutyl alcohol
Alcohols, CnH2n+1OH, ROH (-ol), alkanols, the two
simplest alkanols: methanol (methyl alcohol) (CH3OH), and ethanol
alcohol) (C2H5OH), in alcohols, ROH, the R is not
specific. Alkanol is a type of alcohol ROH, but R must be an
Alkanol, aliphatic alcohol, alkyl alcohol, ROH (Prefix: hydroxy-), (Suffix:
-ol) (-OH: alcohol)
Alcohols are organic compounds with the functional group -OH, but when
attached to an aromatic ring called phenols.
Alcohols, alcohols group: (-OH) Suffix: (ol)
1-butanol, butan-1-ol, n-butyl alcohol, CH3(CH2)3OH
2-butanol, butan-2-ol, sec-butanol, sec-butyl alcohol, CH3CHOHCH2CH3
tert butanol, tert-butyl alcohol, 2-methylpropan-2-ol (CH3)3COH,
CH3CH3COHCH3, simplest tertiary alcohol
Alcohols, R-OH, are compounds in which a functional group, the hydroxyl
group, -OH, is attached to a saturated carbon atom,
The "hydroxyl" refers to the radical HO-.
The "alcohol" in alcoholic beverages is ethanol, ethyl alcohol, CH3CH2OH.
Alcohol 220.127.116.11a Ethanol safety
Do not heat ethanol over an open flame but use a water bath.
However, ethanol may be use in small quantities in alcohol burners to measure
heat of combustion and for reaction with alkanoic acids
to form esters.
Ethanol forms violently explosive mixtures with nitric acid and other
Ethanol with acidified dichromate solutions is highly exothermic.
Ethanol reacts violently with potassium.
Alcohol flammability, ethanol > 70% (PG II), < 70% (e.g. 24%) (PG
III), < 24% not classified as "dangerous goods" 16.1.3a Propanol (C3H7OH)
1. Propan-1-ol, 1-propanol (n-propyl
alcohol) (CH3CH2CH2OH), Highly flammable,
Toxic if ingested
2. Propan-2-ol, 2-propanol (iso-propyl
alcohol) (CH3CH(OH)CH3), C3H7OH, sec-propyl
alcohol, rubbing alcohol, Flammable
Potassium dichromate as an oxidizing agent, propan-2-ol (isopropanol)
--> propanone (acetone) + water: 15.2.3,
(See: 5.) 16.1.3b Butanol (C4H9OH)
Butanol, butyl alcohol (C4H9OH) has 4 isomers:
("Butanol" may refer to either butan-1-ol or butan-2-ol.)
1. Butan-1-ol, n-butanol, 1-butanol, n-butyl alcohol, butyl alcohol,
(primary alcohol), CH3(CH2)3OH (C4H9OH),
(biobutanol), product of carbohydrate fermentation, common flavourant
2. Butan-2-ol, sec-butanol, 2-butanol, sec-butyl alcohol (secondary alcohol)
secondary butyl alcohol, s-butyl alcohol, product of grain and hops fermentation
3. isobutanol, isobutyl alcohol, IBA (CH3)2CHCH2OH,
(C4H9OH), 2-methylpropan-1-ol, 2-methyl-1-propanol,
additive to reduce
viscosity, flavouring agent
4. tert-butanol, t-butanol, tert-butyl alcohol (CH3)3COH,
C4H10O, 2-methypropan-2-ol, 2-methyl-1-propanol,
(simplest tertiary alcohol, so is often just called "butyl alcohol" or
"butanol", with the hydroxyl on the same carbon with three methyl
groups.), paint remover, solvent, Harmful by all routes, flammable 16.1.3c Butyl glycol (C4H9OCH2CH2OH)
2-butoxyethanol, butyl cellosolve, C4H9OCH2CH2OH,
butyl ether of ethylene glycol, pH 11, in window cleaner "Windex", inks,
solvents 18.104.22.168.1 Dihydric alcohols,
The dihydric alcohols, glycols, diols, have two hydroxyl groups on different
carbon atoms, e.g.:
1. Ethane-1, 2-diol, ethylene
glycol, ethanediol, "glycol", 1.2-dihydroxyethane (C2H4O)nH2O,
(CH2OHCH2OH), b.p. 197.5oC, car
radiator antifreeze, coolant, in hydraulic fluids, paint and plastic solvent,
sweet taste but poisonous
2. Butane-1, 4-diol, C4H10O2, [HO(CH2]4OH],
CH2CH2 (oxidation) --> CH2OCH2
(+ water) --> HOCH2CH2CH2CH2OH
ethene (oxidation) --> epoxyethane (+ water) --> ethane-1.2-diol
3. Propane-1, 2 diol, propylene glycol, C3H8O2,
CH3CHOHCH2OH, colourless, tasteless, odourless, solvent
preparations 22.214.171.124.2 Trihydric alcohols,
The trihydric alcohols, have three hydroxyl groups on different carbon
atoms, e.g. 1.2, 3-trihydoxypropane, glycerol
[HOCH2CH(OH)CH2OH] 126.96.36.199.3 Nitroglycerine
Nitroglycerine (UK), Nitroglycerin (USA)
glycerol + cold mixture of concentrated sulfuric acid + nitric acid -->
nitroglycerine, ester of nitric acid
Nitroglycerine is a colourless, insoluble oil, solidifies on cooling,
contact explosive, used to make dynamite and cordite.
Dynamite is nitroglycerine surrounded by a ring of diatomite, diatomaceous
earth, kieselgur, SiO2Al2O3Fe2O3.
Cordite is a smokeless explosive powder, shaped as cords, e.g. gun cotton
+ nitroglycerine + petroleum jelly
Nitroglycerine is a very unstable liquid that explodes if given a slight
It freezes at 13oC, but is more likely to explode if solid.
It is used to make safer explosives, e.g. dynamite.
It is also used in very small tablets for the heart condition angina pectoris
where people get out of breath and suffer pain in the chest
from over-exertion. 188.8.131.52.4 Nitrocellulose,
This preparation is too dangerous to be done in schools.
Potassium nitrate is dissolved in concentrated sulfuric acid to produce
a dangerous vapour, then cooled in an ice and salt mixture, then
cotton balls are added.
Later more sulfuric acid is added, then the cotton balls are removed and
placed in sodium bicarbonate solution until no more bubbles
form, then dried. 184.108.40.206.1 Alcohols, primary,
secondary and tertiary aliphatic alcohols
Primary alcohols RCH2OH, Secondary alcohols R2CHOH,
Tertiary alcohols R3COH See 3.38: Carbon dioxide and fermentation
for brewing See 16.5.10: Rubbing alcohol, surgical
spirit 220.127.116.11.1a Tests for alcohols, potassium manganate
(VII) Primary alcohols
Primary alcohols, e.g. methanol (methyl alcohol, CH3OH), propanol
(isomer propan-1-ol, n-propyl alcohol, CH3CH2CH2OH),
and butan-1-ol (1-butanol, n-butanol, CH3(CH2)3OH),
have two hydrogen atoms attached to the carbon atom attached to the
hydroxyl group (-OH).
So they all have -CH2OH in their molecules.
They can be directly oxidized to aldehydes or carboxylic acids using oxidizing
(O)R1-CH(OH)-R2 --> R1-C(O)-R2(O)R-CH2OH
--> R-CHO(O)R-CHO --> R-COOH
1.1 Allyl alcohol, CH2:CHCH2OH, prop-2-en-1-ol,
2-propen-1-ol, Highly toxic by all routes Secondary alcohols
Secondary alcohols, e.g. propan-2-ol (CH3)2CHOH,
rubbing alcohol, isopropyl alcohol and secondary butyl alcohol, butan-2-ol
(CH3CH2CH[CH3]OH), [ or CH3CH(OH)C2H5],
have one hydrogen atom attached to the carbon atom attached to the hydroxyl
So they all have (-CHOH), in their molecules.
They can be slowly oxidized to ketones.
(O)R1-CH(OH)-R2 --> R1-C(O)-R2 Isopropanol,
isopropyl alcohol Tertiary alcohols
Tertiary alcohols, e.g. 2-methylpropan-2-ol, 2-methyl-2-propanol (CH3)3COH,
tertiary butyl alcohol has no hydrogen atom
attached to the carbon atom attached to the -OH group.
So they all have -COH in their molecules. 18.104.22.168.1a Tests for
alcohols, potassium manganate (VII)
Tests for primary, secondary and tertiary aliphatic alcohols
To one drop of each alcohol in three test-tubes, add saturated potassium
manganate (VII) solution drop by drop with shaking.
If decolorization occurs, continue adding drops until pink colouration
persists, as shown by spot testing on filter paper.
Add one drop of concentrated sulfuric acid and resume adding potassium
manganate (VII) drop by drop.
No decolorization occurs with tertiary alcohols.
The colour eventually fades with secondary alcohols, but persists with
primary alcohols. 22.214.171.124.2 Prepare sodium
Sodium ethoxide is the salt of a weak acid, ethanoic acid, and a strong
base, sodium hydroxide.
Add a pinhead size piece of sodium to 1 mL of ethyl alcohol.
Tests for hydrogen gas:
Na (s) + 2C2H5OH (l) --> 2C2H5ONa
(s) + H2 (g)
sodium + ethanol --> sodium ethoxide + hydrogen
Evaporate the sodium ethoxide solution to form white crystals.
Add drops of water and tests for litmus that turns blue. 126.96.36.199 Phenols
Phenols, group: (OH-C), in a benzene ring, Phenol = (C6H5O6)
| See diagram 188.8.131.52: Phenols, quinones,
naphthols, coniferyl alcohol (p-coumaryl alcohol), urushiol, organohalogens
| See diagram 184.108.40.206: Phenols, quinones
| 220.127.116.11: Antioxidant phenols,
antioxidants, vitamin E, beta carotene
| 18.104.22.168.0: Cholesterol, C27H46O
1. Phenols, Ar-OH, are compounds with an hydroxyl group, -OH, firmly attached
to an aromatic ring, e.g. benzene, 2-naphthol,
Phenols, group: (OH-C), in a benzene ring, Phenol = (C6H5O6):
Phenols (hydroxyl group -OH), connected to a carbon atom in a benzene
ring, benzene-OH, hydroxybenzenes
The -OH is so firmly attached that the O-H bond tends to break to lose
an H+ ion to form a weak acid.
2. Phenols divided into mono-, di-, tri- tetra-, and polyhydric phenols,
e.g. p-chlorophenol, C6H4ClOH, 2, 4, 6-tribromophenol,
Chlorophenol red, C19H12Cl2O5S,
(acid-base indicator): 8.0
PLA synthetic fibre, polylactic acid, polylactide 22.214.171.124a Pyrogallol
Pyrogallol, C6H3(OH)3, 1.2, 3-trihydroxybenzene,
white crystals, reducing agent, alkaline solution (use sodium
hydrogen carbonate not sodium hydroxide), reacts with oxygen in the air
to form a brown polymer.
Pyrogallol is used in experiments where oxygen must be eliminated from
a gas or from the air.
Pyrogallol is prepared by heating gallic acid, C6H2(OH)3COOH,
(3, 4, 5-trihydroxybenzoic acid). 126.96.36.199.2 Naphthols See diagram 188.8.131.52: Phenols, Quinones,
naphthols | See 184.108.40.206: Tests for
carbonates, Molisch's test (α-naphthol test)
1-naphthol, C10H7OH, a-naphthol, α-naphthol, naphthalen-1-ol,
tests for carbonates
2-naphthol, C10H7OH, b-naphthol, beta-naphthol,
naphthalen-2-ol, white solid, antioxidant in rubber products, antiseptic,
primary amines 220.127.116.11.3 Cresols See Cresylic acid, CH3C6H4OH,
"cresol (mixture of the three isomers of cresol)"
Cresols are methyl phenols, C7H8O, CH3C6H4OH,
produced from coal tar creosote or by methylation of phenol
"Cresol" used as a disinfectant is usually a cresol mixture: o-cresol,
Toxic by all routes
(o-Cresol, ortho-cresol, 2-Methylphenol), colourless crystals
(m-Cresol, meta-cresol, 3-Methylphenol), liquid
(p-Cresol, para-cresol, 4-Methylphenol), solid 18.104.22.168.4 Resorcinol See diagram 22.214.171.124: Resorcinol
Resorcinol, C6H4(OH)2, [benzene-1, 3-diol]
is a dihydric phenol used with formaldehyde (methanal, HCHO)
Resorcinol, crystals, resorcin, m-dihydroxybenzene, 1.3-dihydroxybenzene,
1.3 benzenediol (a dihydroxy phenol)
Resorcinol is harmful, corrosive to skin.
Resorcinol, Solution <10%, Not hazardous, but do not ingest
Resorcinol (test reagent in ethanol), explosive with nitric acid, turns
red in light, antiseptic, colourless crystals, used for cold-setting
adhesives with formaldehyde, also used to make plasticizers, resins and
Resorcinol, C6H6O2, argan oil, in Argania spinosa.
Prepare formaldehyde resorcinol resin: 126.96.36.199
Resorcinol, Xanthene dyes: 188.8.131.52 184.108.40.206.5 Triclosan See diagram 220.127.116.11: Triclosan
Triclosan, 5-chloro-2-(2, 4-dichlorophenoxy) phenol, C12H7Cl3O2,
is an organohalogen polychlorophenoxy phenol used in
anti-bacterial and anti-fungal products, and in low concentrations in many
other products, including toothpaste, mouthwash, deodorants,
soap, scent, detergent dishwashing liquid, hand washes, at high concentrations
is harmful by inhalation, irritant, environmental danger
Triclosan is suspected of causing bacterial resistance because of it widespread
use and occurrence in the environment and may weaken
the immune system.
Other organohalogens include: 2, 4, 6-trichlorophenol, 2, 4, 6-tribromianisole,
2, 4, 6-trichloroanisole, chlorophenol compounds +
filamentous fungi --> 2, 4, 6-trichloroanisole. 18.104.22.168 Thiols (Mercaptans) See diagram 22.214.171.124: Thiophenol (phenyl
mercaptan), | See diagram 16.13.10: Metam,
Thiols (mercaptans), thio alcohols, Thioalcohols group: (-SH), Suffix:
(-thiol) (SH in an organic compound)
Thiols, thio-alcohols (RSH, R not equal to H) (sulfhydryl group: -SH,
characteristic of thiols).
(Suffix: -thiol), [old name: mercaptans, because react with mercuric ion
to produce mercaptides (RS)2Hg], e.g. methanethiol, methyl
mercaptan (CH3SH), ethanethiol (MeCH2SH), ethyl
mercaptan (ethanethiol or ethan-ethiol or captan) (C2H5SH),
thiophenol, phenyl mercaptan Ph-SH, sodium thiolate: (RS-Na+)
Thiols, RS-H, are oxidized to disulfides, RS-SR. 126.96.36.199a Methanethiol
The methylmethionine and asparagusic acid, α-aminodimethyl-γ-butyrothetin,
in asparagus may produce malodorous methanethiol,
dimethyl disulfide and dimethyl sulfone in people who eat asparagus.
However, less than 50% of adults can smell these compounds in the urine.
Family studies suggest that the ability to produce the odorous urine is
inherited as an autosomal dominant trait. 188.8.131.52.1 Methyl mercaptan
Methyl mercaptan, methanethiol, CH3SH (MeSH), colourless gas,
very flammable, offensive rotten cabbage or
decomposing vegetables smell in bad breath and flatus, in some nuts and
cheese 184.108.40.206.2 Allyl mercaptan
Allyl mercaptan, flavouring agent, 2-propene-1-thiol, from garlic, C3H6S,
EC Number (EINECS): 870-23-5
Odour threshold value: 6 × 107 molecules / mL of air 220.127.116.11.3 Ethyl mercaptan
Ethyl mercaptan, ethanethiol, CH3CH2SH, colourless
gas, offensive rotten cabbage smell, poisonous and used as
oderant in LPG gas at less than poisonous concentration to allow early
detection of gas leaks
There is some evidence that very old men cannot smell it and so are susceptible
to LPG gas poisoning. 18.104.22.168.4 Thiophene
Thiophene, thiolane, THT (CH2)4S, tetrahydrothiophene,
colourless, unpleasant odour gas, used as odorant in natural gas and LPG
gas (not in USA) 22.214.171.124.5 Phenothiazine,
PTZ, C12H9NS 11.12.1 Tranquillizers 1, major tranquillizers See diagram: 14.05, Phenothiazine, S(C6H4)2NH
Phenothiazine, light green powder turns green-blue in sunlight, psychoactive
drug, antiemetic, antihistaminic, anticholinergic, prevents
emesis. 126.96.36.199 Ethers 1.13 Ethers, List of ethers
Ethers have two hydrocarbon groups linked by one oxygen, and have compounds
in the form: R1OR2 (R not equal to H), where R1
may or may not be the same as R2, e.g. the anaesthetic diethyl ether. Ethers (ROR') (CnH2n+2O), alkyl ethers, ethoxyethane
ether, e.g. dimethyl ether (CH3OCH3) 188.8.131.52 Ethyl cellulose
Ethyl cellulose, C20H38O11, cellulose
ethyl ether, "Aquacoat", food additive emulsifier E462, prepared from cellulose
in wood and
chemically ethylated (i.e. some hydroxyl groups converted to ethyl ether
groups), food stabilizer and thickening agent, filler, dietary fibre,
anti-clumping agent, emulsifier.
Ethyl cellulose is no longer permitted as emulsifier in the EU, because
it can be fermented in the large intestine to cause bloating,
constipation and diarrhoea. 184.108.40.206 Acetates
Acetates (ethanoates), ROAc, salt or ester of ethanoic acid (acetic acid)
As a salt: sodium acetate, sodium ethanoate (CH3COONa).
As an ester: ethyl ethanoate (CH3COOC2H5) 220.127.116.11 Benzoyl
Benzoyl group, benzene carbonyl group C6H5CO-,
e.g. benzoyl chloride (C6H5COCl) 18.104.22.168 Acetal
Acetal (alcohol + aldehyde), RCH(OR')2, where R and R' = organic
radicals and R may be hydrogen
Acetal, 1.1-diethoxy ethane, CH3CH(OC2H5)2,
is a colourless flammable solvent, smelly liquid
It is formed by reaction of acetaldehyde with ethanol.
Hemiacetals: [RCH(OH)R'], Di-methyl acetals: [RC(OMe)2R'],
Di-ethyl acetals: [RC(OEt)2R'] (polyacetals, polyoxymethylene
POM) 22.214.171.124 Salts
Salts, e.g. sodium ethanoate (sodium acetate) (CH3COONa),
ammonium acetate (CH3COONH4)
NaHCO3 + CH3COOH --> CH3COONa + H2O
+ CO2 (g) 126.96.36.199 Saturated hydrocarbons,
e.g. hexane, C6H14
All carbon atoms in the compound have either four or three hydrogens bonded
to them and no double bonds, triple bonds or rings.
They react in almost the same way, as in ignition test and bromine water
test. 188.8.131.52 Tests for unsaturated hydrocarbons,
bromine water tests for unsaturation 184.108.40.206 Tests for unsaturated hydrocarbons,
ignition tests for unsaturation 220.127.116.11 Acyl halide
Acyl halide, acid chloride, Acid chlorides group: (-COCL), Suffix: -oyl
Acyl chloride (RCOCl), e.g. ethanoyl chloride (acetyl chloride, CH3COCl) 18.104.22.168 Amides
Amides, acid amides (-amide) (amide group: -CONH2, RCONH2),
Suffix: -amide, e.g. urea (H2NC=ONH2)
[IUPAC: Do NOT distinguish amides with NH2, NHR, NR2
groups by the terms "primary, secondary, tertiary".]
1. Primary amides RCONH2, e.g. alkanamides: ethanamide (acetamide),
(CH3CONH2) propanamide (C2H5CONH2)
2. Secondary amides, N-substituted amides RCONHR'
3. Tertiary amides RCNR'R"
Secondary or tertiary amides have the prefix N, e.g. N-ethylethanamide
N.N-dimethylmethanamide HCON(CH3)2 (the polymer
group -CO-NH-) (inorganic amides, e.g. KNH2) 22.214.171.124a Carbamates See diagram 16.13.7: Carbamates, carbaryl,
Carbamates are derivatives of carbamic acid, NH2COOH.
Urethanes are esters of carbamic acid, i.e. alkyl carbamates.
Examples of carbamates: carbamic acid, ammonium carbamate, bendiocarb,
carbaryl, oxamyl, propoxur, urethane.
Combustion of carbamates may produce noxious NOx and carbon monoxide.
Carbamates are more reactive than amides and can form polyurethane resins.
Carbamates are incompatible with strong acids and bases, strong oxidizing
acids, and peroxides.
Many carbamates are used as pesticides because of their anticholinesterase
activity, e.g. carbaryl, propoxur, bendiocarb and methomyl. 126.96.36.199.1 Acrylamide
Acrylamide, C3H5NO, 2-propenamide, ethylene carboxamide,
acrylic amide, propenoic acid, UN 2074, vinyl amide, is toxic if ingested,
crystalline form and aqueous solutions, monomer or polymer.
Acrylamide, C3H5NO, CH2CHCONH2,
is the amide of acrylic acid, propenoic acid (CH2CHCOOH), an unsaturated liquid
Acrylamide is a poison, harmful if swallowed, inhaled or absorbed through skin, affects central and peripheral nervous systems and
It causes irritation to skin, eyes and respiratory tract, suspected cancer hazard depending on level and duration of exposure, possible
birth defect hazard.
It is thermally unstable, but can polymerize explosively if heated to the melting point.
It is most common in overcooked French fries and potato chips, also burned toast and burned high carbohydrate foods.
The European Food Safety Authority (EFSA) recommends consuming golden rather than dark brown or black toast, short espresso
rather than lungo, and avoiding overcooked foods.
Acrylamide is a toxic chemical which could cause tumours.
It is not deliberately added to food by manufacturers, it is a by-product of the cooking process and has always been around.
A lot of research has been done into the chemical's effect on humans, first highlighted as a potential risk in a 2002 Swedish study.
In 2015, the European Food Standard Agency (EFSA) published its first full risk assessment of acrylamide in food, which found that the
chemical potentially increases the risk of cancer for all age groups.
The FSA explain: "This means that acrylamide might contribute to your lifetime risk of developing cancer, although it is not possible to
estimate how big this contribution may be.
Eating too much processed and red meat, and cooking meat at high temperatures on grills and BBQs, could also increase your cancer risk.
"Coffee has been shown, over and over again, to be a healthy beverage," said William Murray, president and chief executive of the National
Coffee Association, in reaction to the decision.
A previous case resulted in potato-chip makers agreeing in 2008 to pay $3 million and remove acrylamide from their products.
The chip-makers opted to do that rather than post cancer warnings like those that are found, and largely ignored, throughout California.
He argued the lawsuit "does nothing to improve public health."
Kathryn M. Wilson, a cancer epidemiologist at Harvard University, told the LA Times: "I think the evidence that acrylamide makes a difference
for human cancer risk is pretty weak."
31/3/2018 LOS ANGELES
A Los Angeles judge determined that coffee companies must carry a cancer warning label because of a chemical produced in the roasting process.
The judge said Wednesday that Starbucks and other companies failed to show that benefits from drinking coffee outweighed any risks.
He ruled in an earlier phase of trial that companies had not shown the threat from the chemical was insignificant.
The Council for Education and Research on Toxics, a nonprofit group, sued Starbucks and 90 other companies under a state law that requires
warnings on a wide range of chemicals that can cause cancer, including acrylamide, a carcinogen present in coffee. 188.8.131.52 Acid anhydrides
Acid anhydrides, acyl anhydrides, anhydrides [RCO-O-COR' (R(C=O)O(C=O)R')],
e.g. ethanoic anhydride (acetic anhydride),
[(CH3CO)2O], ethanoic anhydride [CH3(C=O)O(C=O)CH3],
trifluoroethanoic propanoic anhydride [CH3CH2(C=O)O(C=O)CF3] 184.108.40.206 Imides
Imides (R1CO-NH-COR2) (imido group: -CONHCO-), e.g. gluthemide (C13H15NO2).
The polymer group (-CO-NR-CO), polyimides, N-(trichloromethylthio), cyclohex-4-ene-1,2-dicarboyimide 16.1.12
Fractional distillation of crude oil
A fractionating column is used to separate the distillates that boil within
a temperature range, i.e. the "fractions".
Fractional distillation of crude oil: petroleum gas (LPG), naphtha, petrol
(gasoline), kerosene (paraffin oil), diesel oil, lubricating oil
(motor oil), paraffin wax (fuel oil), residuals (bitumen, "tar", asphalt,
The word "asphalt" can refer to natural bituminous pitch, e.g. the Trinidad
Pitch Lake, or the fraction of crude oil produced by
distillation or the "hot mix" mixture of aggregate and bitumen used to
surface roads, paths and school playgrounds. Mineral oil
Mineral oil, low value byproduct of petroleum distillation, usually 15o
C to 40o C, many uses, lubricating light oil. Hydraulic fluid
Hydraulic fluid, mineral oil with low compressibility, needs correct viscosity
for different machines 220.127.116.11 Petroleum gas
Petroleum gas (methane, ethane, propane, butane), Mix of 1 to 4 carbon
atoms, boiling range < 40oC.
Liquefied under pressure as LPG (liquefied petroleum gas), a mixture mainly
of propane (C3H8), and butane (C4H10). 18.104.22.168 Naphtha
Naphtha (petroleum naphtha, ligroin), processed to make gasoline
Mix of 5 to 9 carbon atoms, mainly aliphatic, e.g. alkanes, boiling range
120oC to 180oC, or < 200oC.
The light hydrocarbon cut between gasoline and kerosene.
(Another naphtha can also be produced from coal tar.) 22.214.171.124 Petrol
Petrol, "gas", gasoline, motor fuel
Mix of C6H14 to C11H24, 5
to 12 carbon atoms, alkanes and cycloalkanes, boiling range 40 to 205oC 126.96.36.199 Kerosene
Kerosene, kerosine, paraffin oil, jet engine fuel, tractor fuel
Mix of C12H26 to C15H32,
10 to 18 carbon atoms, alkanes and aromatics, boiling range 175oC
to 325oC 188.8.131.52 Diesel oil
Diesel oil, gas oil or diesel distillate, diesel fuel, heating oil
Mix of C15H32 to C18H38,
12 or more carbon atoms, alkanes, boiling range 250oC to 350oC 184.108.40.206 Lubricating oil
Lubricating oil, motor oil, grease
Mix of C16H34 to C24H50, 20
to 50 carbon atoms, alkanes and cycloalkanes and aromatics, boiling range
300oC to 370oC 220.127.116.11 Paraffin wax
Paraffin wax, heavy gas, fuel oil
Mix of C20H42 and higher hydrocarbons, 20 to 70 carbon
atoms, alkanes and cycloalkanes and aromatics, boiling range 370oC
600oC 18.104.22.168 Residuals
Residuals, bitumen, "tar", asphalt, waxes
A mix of C24H50 and higher hydrocarbons, multiple-ringed
compounds, 70 or more carbon atoms, boiling range > 600oC
Petroleum jelly is a saturated semi-solid of crystalline
and liquid hydrocarbons, carbon numbers < C25, made by dewaxing paraffinic
Naphtha, "Greek fire", was an inflammable bituminous substance used in
warfare. 16.1.13 Prepare triodomethane
(iodoform) See 1.6: Iodine solution, tests for starch
| See diagram 16.2.2: Halogen compounds,
Add five drops of iodine solution to five drops of ethanol.
Add drops of dilute sodium hydroxide solution until the brown colour of
Observe the crystals under a microscope.
C2H5OH + 4I2 + 6NaOH --> HCOONa +
5NaI + 5H2O + CHI3
ethanol + iodine + sodium hydroxide --> sodium methanoate (sodium formate)
+ sodium iodide + water + triodomethane (iodoform) 16.1.14 Prepare trichloromethane
(chloroform) Trichloromethane, CHCl3,
chloroform See diagram 16.1.7: Prepare chloroform | See 16.2.2: Chlorinated hydrocarbons, haloalkanes
Bleaching powder is usually a mixture of calcium chlorate (I) [basic calcium
chloride, calcium hypochlorite], calcium chloride and
calcium hydroxide prepared by passing chlorine gas through a calcium hydroxide
Calcium chlorate (I) oxidizes ethanol to ethyl aldehyde.
Aldehydes or ketones have a hydrogen atom attached to the carbon atom
attached to the carbonyl group, C=O.
This hydrogen atom can be replaced by a halogen atom to form halogen compounds.
If a molecule contains three such hydrogen atoms, e.g. ethanol and propanone
(acetone) molecule, a trihalide may be formed,
e.g. trichloromethane (chloroform, CCl3).
H3C-C(O)-R + 3OX --> X3C-C(O)-R
ketone or aldehyde hypochlorite --> trihalide
The trihalide decomposes in a basic solution to a haloform (CHX3),
e.g. CHCl3C-C(O)-R (l) + OH- (aq) --> CHCl3
(l) + RCOO- (aq) 22.214.171.124 Reaction of acetone
with bleaching powder
CH3COCH3 + 3Cl2 --> CCl3COCH3
2CCl3COCH3 + Ca(OH)2 --> 2CHCl3
Ca(OH)2 + 2HCl --> CaCl2 + 2H2O 126.96.36.199 Reaction of ethyl
alcohol with bleaching powder
C2H5OH (l) + Cl2 (g) --> CH3CHO
(l) + 2HCl (aq)
ethyl alcohol + chlorine --> ethyl aldehyde
CH3CHO (l) + 3Cl2 (g) --> CCl3CHO
(l) + 3HCl (aq)
2CCl3CHO (l) + Ca(OH)2 (aq) --> 2CHCl3
(l) + (HCOO)2Ca (aq)
Be careful! Do not allow any flames in the laboratory!
Grind together in a mortar and pestle 5 g bleaching powder and 10 mL water.
Put the mixture into the test-tube of the gas preparation apparatus.
Cool the test-tube.
Add either 4 mL ethanol in 2 mL water or 4 mL propanone (acetone) in 2
mL of water.
Swirl the contents of the test-tube and keep it cool.
Use an electric water bath to warm the temperature to 55oC.
Water and trichloromethane condense in the receiving test-tube leaving
a calcium salt solution in the test-tube.
Add water to the distillate and separate the trichloromethane with a separating
funnel. 16.2.3 Organometal compounds
(prefix the metal with organo-), e.g. organomagnesium compounds.
MeMgI iodo(methyl)magnesium, Et2Mg diethylmagnesium 188.8.131.52 Carbides, C4-
Carbide are binary compounds of:
1. C + electropositive element, e.g. calcium carbide.
2. C + heavy metal for cutting tools, e.g. aluminium carbide (Al4C3),
chromium carbide, Cr3C2, iron carbide Fe3C
Tungsten carbide ("carbide", WC), is used for cutting tools, milling tools,
Iron carbide is formed with carbon monoxide when iron oxide is heated
3Fe2O3 +11C --> 2Fe3C + 9CO (g) Types of carbides 1. Methanides
Methanides, e.g. aluminium carbide, Al4C3
Hydrocarbyl anions, methyl anion, conjugate base of methane
Methanides + water --> methane, e.g. aluminium carbide (Al4C3) 2. Acetylides
Acetylides, salts of acetylide anion C22- (percarbide)
Formed by alkali metals, alkaline earth metals, lanthanoid metals, e.g.
sodium carbide Na2C2, copper (I) acetylide Cu2C2,
lanthanum carbide LaC2, aluminium carbide Al4C3,
calcium acetylide CaC2, cementite Fe3C (iron carbide),
copper (I) acetylide
Acetylides (percarbides, C22-) + water --> acetylene,
e.g. Na2C2, CaC2
Calcium carbide CaC2 (calcium dicarbide, "carbide", calcium
acetylide, acetylenogen, ethnide dicarbide, Toxic by all routes
CaC2 + 2H2O --> C2H2 +
calcium carbide + water --> acetylene + calcium hydroxide 3. Sesquicarbides,
C34-, e.g. Mg2C3 4. Covalent carbides
Covalent carbides, e.g. boron carbide B4C, silicon carbide,
See: Models, inorganic,
carborundum (silicon carbide), 30 "atoms", "Scientrific" (Commercial)
Silicon carbide, SiC, carborundum, abrasive, moissanite synthetic gemstone,
emery paper, sanding paper, sharpening stone, fine
particles, Toxic by inhalation 16.2.4 Nitrogen compounds,
one atom of nitrogen See 184.108.40.206: Amides 220.127.116.11 Nitriles Nitrile
Nitriles (acid nitriles, alkyl cyanides, cyanides) (-CN, R-C triple bond
N) (note triple bond), Cyanide ion: CN- e.g. ethane nitrile,
Ascetonitrile (methyl cyanide, ) (CH3CN),
Acrylonitrile for making
Orlon (vinyl cyanide, 1-cyanoethene) (CH2=CH-CN) 18.104.22.168.1 Cyanamides
Cyanamides (inorganic, CN22-), ionization reaction
of methylamine See diagram 22.214.171.124.1: Melamine
cyanic acid (fulminic acid) (HOCCN) (cyanates, fulminates), Isocyanic
acid (H-N=C=O), isocyanates
(isocyanate group: -NCO, HN=C=O), isocyanides (HNC), hydrocyanic acid
CaCn2 + H2O + CO2 --> H2NCN
calcium cyanamide + water + carbon dioxide --> cyanamide + calcium
(NH2)2CO --> HCNO + NH3
urea --> cyanic acid + ammonia
6HCNO --> C3H6N6 + 3CO2
cyanic acid --> melamine + carbon dioxide
6(NH2)CO --> C3H6N6 + 6NH3
Melamine, C3H6N6, 2, 4, 6-triamino-1.3,
5-triazine is 66% nitrogen w/w and is used in the plastics industry.
Unfortunately, its high nitrogen content has been the reason for its use
as a powdered milk pollutant in China resulting in death and
kidney problems in young babies due to the formation of kidney stones.
Melamine-formaldehyde (MF), C4H6N6O,
hard to ignite, alkaline fumes, burns with pale yellow flame (light blue-green
formaldehyde and fish-like smell, thermosetting plastic, retains strength
and shape on heating
Melamine crockery, green, virtually unbreakable, dishwasher safe, Not
suitable for microwave oven, plate, 18 mm diameter 126.96.36.199.0 Amines
Amines, aliphatic amines (RNH2-, R = alkyl group),
ionization reaction of methylamine
Amines have lower boiling temperatures than alcohols.
Methylamine and ethylamine are gases at room temperature.
Longer chain amines are volatile liquids with rotten fishy smells characteristic
of decomposing proteins
Amines are bases (can accept a H+ ion), so can react with
acids to form salts and lose the fishy smell.
1. Primary amines: R-NH2
NH2- = amino group, e.g. methylamine (CH3-NH2),
ethylamine (CH3CH2-NH2). Aniline, C6H5NH2,
2. Secondary amines: R2-NH
NH = imino group, e.g. dimethylamine (CH3)2NH
3. Tertiary amines: R3-N
N = nitrogen, e.g. Triethylamine, C6H15N Trimethylamine, C3H9N Physostigmine, C15H21N3O2,
tertiary amine 188.8.131.52.01 Methylamine
CH3NH2 + H2O <--> CH3NH3+
+ OH- methylamine + water <--> methylammonium ion + hydroxide ion 184.108.40.206.02 Prepare phenylamine
1. Benzene + concentrated nitric acid + concentrated sulfuric acid -->
2. Nitrobenzene + tin catalyst Sn + reducing agent hydrochloric acid -->
phenylamine + water
C6H5NO2 + 6 H+ --> C6H5NH2
+ 2H2O 220.127.116.11.03 Nitrosamines
Nitrosamines are produced by reaction of nitrous acid with secondary amines.
They can be formed in the gut when nitrites react with amino acids.
C4 explosive, H8N8O8, HMX, Octogen,
detonator, solid rocket propellant, mainly cyclonite or cyclotrimethylene
RDX explosive (Research Department Explosive, C3H6N6O6,
Cyclonite, Hexagen, used against German submarines during World
War II 18.104.22.168.04 Nitramine Nitramine (acid-base indicator, 3.5),
C7H5N5O8, tetryl, colourless-yellow
crystals, explosive formerly used in munitions 22.214.171.124.05 Clenbuterol,
Performancing-enhancing drug banned by the International Olympic Committee.
It is illegally used to build skeletal muscle and increase metabolism,
but may cause heart attacks.
Clenbuterol is a substituted phenylaminoethanol that has beta-2 adrenomimetic
properties at very low doses.
It is used as a bronchodilator in asthma.
Although approved for use in some countries, as 2006 clenbuterol is not
an ingredient of any therapeutic drug approved by the US
Food and Drug Administration. 126.96.36.199.1 Ethylenediamine
ClCH2CH2Cl + 4 NH3 --> H2NCH2CH2NH2
+ 2 NH4Cl
1.2-dichloroethane + ammonia --> ethylenediamine + ammonium chloride 188.8.131.52a Imines
Imines, R2C=NR', Imino group = ring containing (-NH-), or (=NH),
linked to C] (RN=CR', where R = H or hydrocarbyl,
e.g. (ethyl-), O-benzoquinonedimine
Imine primary RC(=NH)R (imino-) (-imine)
Imine secondary RCH=NR (imino-) (-imine) 184.108.40.206b Cyclic imines Pyrroline, C4H7N,
1-Pyrroline Acetyl pyrroline, C6H9NO 220.127.116.11 Nitroalkanes
Nitroalkanes (nitroparaffins) (CnH2n+1NO2)
Nitromethane (CH3NO2), nitroethane, urea (carbamide) 18.104.22.168 Nitrites
(NO2-), dioxonitrate ion, salts or esters of nitrous acid,
Nitrites group: -C=N, Suffix: -nitrite, , e.g. sodium nitrite and potassium
as meat curing agents 22.214.171.124 Oximes
Oximes (hydrox-imino-alkanes), Formula R1R2C=NOH, where R1= organic side
chain and if R2 = hydrogen, aldoxime forms
or if R2 = organic group, ketoxime forms.
(-CNOH group) (ketone or aldehyde + hydroxylamine - water) (RCNOHR'),
e.g. ethanal oxime (acetaldehyde oxime, AAO),
(CH3CH=NOH) 126.96.36.199 Cyanocrylates
Cyanocrylates [(CH2)C(CN)COOR], e.g. "Superglue": Me or Et ester
Ethyl cyanoacrylate, "Superglue", BE CAREFUL! Do not squirt in the eye!
Toxic by all routes.
Commercial: Ethyl 2-cyanoacrylate, liquid, C6H7NO2
GBL, γ-butyrolactone is a naturally occurring colourless oily liquid
with a characteristic odour used as a stain remover and stripper,
(including Superglue). 188.8.131.52 Azide compounds
Azide compounds: (N3-), or (-N3), (-N=N+N-),
usually attached to carbon, e.g. sodium azide (NaN3), phenyl
azide or azidobenzene
(C6H5N3), diazine (diimide) (HN=NH),
also, salts of hydrazoic acid, HN3, e.g. sodium azide (NaN3). 184.108.40.206 Azo compounds
Azo compounds: derivatives of diazene (diimide), HN=NH, with both hydrogens
substituted by hydrocarbyl groups, e.g. azobenzene
or diphenyldiazene (PhN=NPh).
hydrazone (ketone + hydrazine (N2H4) - water),
(RC=NNH2R') See: 3.0 Benzopurpurin 220.127.116.11 Diazo compounds
Diazonium ion R-N+N, diazonium compounds [(RNN+)
Cl-], e.g. diazomethane (CH2=N2)
HNO2 and HCl + R-NH2 --> R-N+N + Cl-
nitrous acid and hydrochloric acid + amines --> diazonium ion + chloride
HNO2 + HCl + C6H5NH2 -->
C6H5N2Cl + 2H2O
nitrous acid and hydrochloric acid + phenylamine --> benzenediazonium
chloride + water
benzenediazonium chloride + phenol --> 4-(phenylazo)phenol + NaCl
benzene-N+NCl- + H-benzene-OH + NaOH --> benzene-N=N-Benzene-OH
+ NaCl + H2O
4-(phenylazo) phenol is a yellow dye
Azo dyes of the textile industry use diazonium salts.
The material is first soaked in a soluble salt of phenol or naphthol then
soaked in a diazonium salt so that the dye forms in the cloth. 16.2.6 Phosphorus compounds
Phosphorous compounds, organophosphorus insecticides
Captan fungicide: 16.6.3
Organophosphorus insecticides (mostly thiophosphates), TEPP (tetraethylpyrophosphate,
no longer used as insecticide), parathion,
maldison (Malathion), dimethoate (Rogor), dichlorvos (dimethyl dichlorovinyl
phosphate, DDVP, Shelltox strips), demetron (Systox) See diagram 16.13.6: captan, glyphosate,
1. Phosphonic acid, phosphorous acid [HPO(OH2), H3PO3]
2. Phosphonoglycine 16.7.3 Glyphosate, herbicide
3. Organic phosphates: acephate,
diazinon, dichlorvos, dimethoate, malathion
(maldison), naled, parathion 18.104.22.168 Isothiocyanates Isothiocyanates, R-N=C=S (old name: mustard
oil) (RN=C=S), Mustards: [X(CH2.CH2)2S]
Isocyanate group, R-N=C=O --> isothiocyanate group R-N=C=S Allyl isothiocyanate,
Allyl isothiocyanate, C4H5NS (AITC), CH2CHCH2NCS,
oil of mustard, mustard oil, colourless to yellow, oily liquid, irritating
odour, pungent taste, toxic fumes at high temperature, denser than water,
slightly soluble in water, fumigant, rubefacient, in cruciferous
vegetables, gives pungent taste of mustard, horseradish, wasabi, apotosis
inducer, anti-tumor, anti-oxidant, possibly anti-bladder cancer
in Black mustard | Horseradish | Wasabi See diagram: Allyl isothiocyanate Benzyl isothiocyanate,
Benzyl isothiocyanate (BITC), C6H5CH2NCS,
benyl mustard oil, isothiocyanotaometylbenzene, in cruciferous vegetables,
anti-cancer, apotosis, anthelmintic in Papaya seeds
CH3CH2NCS, ethyl mustard oil Fluorescein isothiocyanate, (FITC),
C21H11NO5S Methyl isothiocyanate (MITC), CH3NCS,
soil fumigant, toxic corrosive, active ingredient in pesticide Metam
Phenethyl isothiocyanate (PEITC), C9H9NS, in cruciferous
vegetables, watercress, possibly anti-prostate cancer
Phenyl isothiocyanate (PITC), C6H5NCS, Edman's
reagent, isothiocyanatobenzene, colourless liquid, pungent odour, used for
acids research sequencing peptides
Sulforaphane (sulfurophane), C6H11NOS2,
broccoli extract 22.214.171.124 Sulfides
Sulfides: RSR (R not equal to H) (old name: thioethers)
Diallyl disulfide C6H10S2, organosulfur
compound, from garlic and other Allium species, Alliaceae.
People who eat asparagus may notice a malodorous over-boiled cabbage smell
in their urine because of sulfur compounds,
e.g. diallyl disulfide, dimethyl sulfide, dimethylsulfone, sulfimides
Diallyl disulfide has health benefits for most people, but some people
are allergic to it and most Allium species. Garlic
Oil of garlic contains diallyl disulfide, diallyl trisulfide and diallyl
Crushing garlic produces allicin, C6H10OS2.
Alliin is a sulfoxide in fresh garlic produced from cysteine.
Allinase is an enzyme active in chopped or crushed garlic.
Allicin, RSR (R not equal to H), Old name: thioethers, garlic
Alliin + allinase --> allicin (allyl thiosulfinate), an unstable antioxidant,
which decomposes to diallyl disulfide (C6H10S2).
C6H11NO3S + allinase --> C6H10OS2.
Allicin causes the smell of fresh garlic. 126.96.36.199 Sulfonium compounds
Sulfonium compounds: R3S+, [SR3]+
Sulfonium salts, e.g. trimethylsulfonium chloride [(CH3)3S]+Cl-,
Cyclopropyldiphenylsulfonium tetrafluoroborate, C15H15BF4S 188.8.131.52 Thiocyanates Thiocyanates: [RC(=O)SN], Salts and esters of
thiocyanic acid, HSCN, e.g. methyl thiocyanate (CH3SCN) 184.108.40.206 Siloxanes
Saturated silicon-oxygen hydrides with chains of alternating silicon and
oxygen atoms, e.g. unbranched [H3Si(OSiH2)nOSiH3],
"Volasil" is octamethylcyclotetrasiloxane.
Dimethylpolysiloxane is an anti-caking agent, emulsifier and anti-foaming
agent. 220.127.116.11 Sulfoxide
Sulfoxide, RS(=O)R', contains a sulfinyl, SO, functional group
Alliin, L-alliin, sulfoxide in fresh garlic
Alliin, L-Alliin, C6H11NO3S, ACSO, S-Allyl-L-cysteine
sulfoxide, SAC, aroma of Garlic Dimethyl sulfoxide
Dimethyl sulfoxide, DMSO, [C2H6OS (CH3)2SO)],
from wood pulp, oyster garlic taste (irritant, penetrates skin, horse
anti-inflammatory, paint stripper, colourless, common solvent, gives garlic
taste after skin contact
Propanethial- S-oxide, C3H6OS, syn-propanethial
S-oxide, a thiocarbonyl S-oxide, lachrymatory factor, in Onion
broken cells --> allinase enzymes + amino acid sulfoxides --> 1-propene
sulfenic acid + lachrymotary factor synthesise enzyme -->
syn-Propanethial -S-oxide which stings eyes 16.5.0 Ethanol
Ethanol, ACS reagent, 99.5% (200 proof), absolute, ethyl alcohol, CH3CH2OH,
C2H5OH, clear, colourless, mobile liquid, volatile
organic compound, inflammable, pleasant odour, burning taste, miscible
with water and most organic solvents, rectified spirit, grain
alcohol, spirit of wine, constant boiling mixture = 95.6% ethanol and
4.4% water, b.p. -78.3oC, absolute alcohol = 100% ethanol, r.d.
0.79 gm cm-3, b.p. 78.5oC, absorbs moisture from
Ethyl alcohol becomes very viscous at liquid nitrogen temperatures.
This is known as 'foetal alcohol syndrome'.
Consumption of ethanol during pregnancy may affect the unborn child,
resulting in spontaneous abortion, developmental problems, or
birth defects, "foetal alcohol syndrome".
Chronic ingestion of ethanol may cause liver cirrhosis and affect the
nervous system. 16.5.1 Methylated spirits
Methylated spirits (95% CH3CH2OH, 5% CH3OH),
or absolute ethanol usually denaturated with 4.8% methanol, but composition
may be legally different in different countries, e.g. Australia 2% methanol
Methylated spirits, methylated ethanol, "spirits" (methylated spirits
sold retail in Australia as 95% ethanol), UN 1170,
duplicator fluid / spirit, Fordigraph spirit duplicator fluid, spirit
vini meth (90% ethanol + 5% v/v methanol, wood alcohol + 5% water),
denatured alcohol, denatured spirits (+ 2% of methyl alcohol, pyridine,
+ other coal tar unpalatable chemicals) (in UK ethanol + 9.5%
methanol + 0.5% pyridine and a blue dye).
The additional substances "denature" the ethanol so it cannot be consumed,
but it may be consumed by Aboriginal people in Australia
by mixing methylated spirits with condensed milk.
Use in illegal home-made alcoholic beverages may cause blindness.
If methylated spirits is swallowed, do NOT induce vomiting, because it
may enter the lungs.
Methylated spirit is highly flammable and must not be used near naked
flames, e.g. boiled in a beaker set on wire gauze over a Bunsen
burner to extract chlorophyll from leaves.
Do not heat methylated spirit over a Bunsen burner, even in a closed container
such as a flask with a reflux condenser, because the
flask may crack.
Methylated spirit burns with a nearly colourless flame so if there is a
fire, be careful of the invisible flames.
Use a carbon dioxide fire extinguisher and fire blankets to smother the
Instead, use a water bath to heat methylated spirit in a flask.
Even if the flask cracks, a mixture of water and methylated spirit is much
less flammable than pure methylated spirit.
Repeated contact of the skin with methylated spirit can cause dermatitis
so wear rubber gloves if using methylated spirit as a solvent for
Do not mix methylated spirit with an oxidizing acid, e.g. concentrated
nitric acid, because a vigorous reaction or explosion may occur.
Use methylated spirit as a cheap low toxicity cleaning solvent for solvent
Observe the rapid changes in colour during the dissolution of plant pigments
in methylated spirits.