School Science Lessons
Topic 16
2024-06-20

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Organic chemistry, Alcohols, Alkanes. Alkenes, Alkynes
(topic16)
Contents
16.1.0 Organic chemistry
16.2.0 Acyclic hydrocarbons
16.3.0 Alkanes CnH2n+2, paraffins
16.4.0 Alkenes, olefins
16.7.0 Alkynes CnH2n-2, acetylenes
16.5.0 Arenes, benzene
16.6.0 Alcohols, phenols, thiols
16.7.1 Cyclic imines
16.8.0 Fractional distillation of crude oil
16.7.2 Imides
16.7.3 Imines
16.11.0 Isothiocyanates
16.9.0 Mercaptans
16.7.4 Methylamine ionization reaction
16.7.5 Nitrosamines
16.7.6 Nitriles
16.7.7 Nitrites
16.7.8 Nitroalkanes (nitroparaffins)
16.7.9 Octane number
16.1.0 Organic chemistry
16.7.10 Organic salts
16.7.11 Organometal compounds
16.3.5 Oximes
16.7.14 Phosphorous compounds
16.7.15 Phenylamine
16.7.16 Saturated hydrocarbons
16.10.0 Sulfur organic compounds
16.6.19 Tests for hydrogen gas:

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16.1.0 Organic chemistry
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.
Be careful! 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
* Acyclic compounds have chains of unbranched or branched carbon atoms.
* Carbocyclic compounds have rings of carbon atoms.
* 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.
Organic compounds
16.1.1 Addition reactions
16.1.2 Oxidation reactions, loss of electrons
16.1.3 Reduction reactions, gain of electrons
16.1.4 Substitution reactions (displacement reactions)

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16.2.0 Acyclic hydrocarbons
| Methane | Ethane | Propane | Butane | Pentane | Hexane | Heptane | Octane | Nonane | Decane |

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acetylenes | aliphatic compounds | alkanes | alkenes | alkyl groups | alkyl radicals | alkynes | olefins | paraffins |

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16.2.1 Acyclic hydrocarbons, alkanes, alkenes
16.3.1 Alkanes CnH2n+2, paraffins
16.5.0 Arenes, benzene
16.2.4 Cycloalkanes
16.6.1.0 Ethane, C2H6, CH3CH3
16.6.2.0, Propane, C3H8
16.6.4.0, Butane, C4H10
16.6.5.0 Pentane, C5H12
16.6.6.0 Hexane, C6H14
16.6.7.0 Heptane, C7H16
16.7.9 Octane number
16.7.9 Octane number
16.2.6 Octadecan-1-ol
16.2.7 Octanol

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16.3.0 Alkanes CnH2n+2, paraffins
Alkanoic acids, RCOOH, -oic acids
16.3.1 Alkanes CnH2n+2, paraffins
16.2.1 Acyclic hydrocarbons, alkanes, alkenes
16.3.3 Friedel-Crafts reaction
16.7.8 Nitroalkanes (nitroparaffins)
16.3.5 Oximes

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16.4.0 Alkenes, olefins
16.4.1 Alkenes, CnH2n, olefins
16.4.2 Prepare ethene
16.4.3 Dienes, diolefins

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16.5.0 Arenes, benzene
16.5.1 Arenes, benzene
16.3.3 Friedel-Crafts reaction
16.5.3 Nitration

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16.6.0 Alcohols, phenols, thiols
16.6.1 Alcohols
16.6.2 Alcohols, primary, secondary and tertiary aliphatic alcohols
16.6.3 Butanol
16.6.4 Butyl glycol
16.6.5 Dihydric alcohols, glycol
16.6.6 Ethanol
16.6.7 Fatty alcohols
16.6.8 Methylated spirits
16.6.9 Naphthols
16.6.10 Nitroglycerine (UK), nitroglycerin (USA)
16.6.11 Nitrocellulose, gun cotton
16.6.12 Phenols
16.6.13 Propanol
16.6.14 Pyrogallol
16.6.15 Resorcinol
16.6.16 Sodium ethoxide, Prepare
16.9.4 Thiols (mercaptans)
16.6.17 Triclosan, organohalogens
16.6.18 Trihydric alcohols, glycerol

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16.1.13 Prepare triodomethane, (iodoform)
16.1.14 Prepare trichloromethane gas (chloroform)
16.1.14.1 Reaction of acetone with bleaching powder
16.1.14.2 Reaction of ethyl alcohol with bleaching powder

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16.8.0 Fractional distillation of crude oil
16.8.1 Diesel oil
16.8.2 Fractional distillation of crude oil
16.8.3 Kerosene
16.8.4 Lubricating oil
16.8.5 Naphtha
16.8.6 Paraffin wax
16.8.7 Petrol
16.8.8 Petroleum gas
16.8.9 Residuals

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16.10.0 Sulfur organic compounds
Sulfur compounds (For the "thio" prefix, replace oxygen by sulfur, e.g. thiobenzamide PhC(=S)NH2.
16.10.1 Allicin
16.10.2 Alliin
16.10.3 Diallyl sulfide
16.10.4 Diallyl disulfide
16.10.5 Diallyl trisulfide
16.11.0 Isothiocyanates
16.10.7 Methanethiol from asparagus
16.10.8 Phenothiazine
16.10.9 Siloxanes
16.10.10 Sulfides
16.10.11 Sulfonium compounds
16.10.12 Sulfoxide
16.10.13 Thiocyanates
16.10.14 Thiophene

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16.9.0 Mercapans
16.9.1 Allyl mercaptan
16.9.2 Ethyl mercaptan
16.9.3 Methyl mercaptan
16.9.4 Thiols (mercaptans)

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16.1.1 Addition reactions
An addition reaction occurs when an atom or atoms are added to a double bond or triple bond unsaturated molecule to fom a new molecule.br> For example, (hydrogenation):
CH2=CH2 (g) + H2 (g) --> CH3CH3 (g)
ethene + hydrogen --> ethane (Pt catalyst)

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16.1.2 Oxidation reactions, loss of electrons
Primary alcohols can be directly oxidized to aldehydes or carboxylic acids.
Primary alkanols (alcohols) -CH2-OH --> alkanals (aliphatic aldehydes)
Example: CH3OH + O2 --> CH2O + H2 (Pt catalyst)
Oxidation of methanol to methanal using a platinum catalyst
CH3OH + O2 --> 2HCHO + 2H2O
methanol + oxygen --> methanal + water
Alkanals --> alkanoic acids, e.g. butanoic acid, CH3(CH2)2COOH

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16.1.3 Reduction reactions, gain of electrons
Alkanals (aliphatic aldehydes) --> primary alkanols (alcohols), -CH2-OH
Experiment
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).

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16.1.4 Substitution reactions, (displacement reactions)
A substitution reaction occurs when an atom or group in a molecule is replaced by another atom or group.
For example, (chlorination, halogenation): Methane with chlorine
Be Careful! Dangerous experiment!
When a mixture of an alkane and chlorine gas are stored at low temperature in the dark no reaction occurs.
At high temperatures or in sunlight, a substitution exothermic reaction, "chlorination" produces chloromethane, and HCl.
CH4 + Cl2 --> CH3Cl + HCl
Excess chlorine can produce dichloromethane, trichloromethane, and tetrachloromethane.
A mixture of chlorine and methane explodes violently in direct sunlight forming hydrogen chloride and free carbon.
BE CAREFUL! Do not mix chlorine and methane!
CH4 (g) + 2Cl2 (g) --> C (s) + 4HCl (g) + energy
Chloromethane, CH3Cl, (methyl chloride)
Dichloromethane, CH2Cl2, (methylene chloride)
Trichloromethane, CHCl3, (chloroform)
Tetrachloromethane, CCl4, (carbon tetrachloride)

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16.2.1 Acyclic hydrocarbons, alkanes, alkenes, alkynes
See diagram 16.1.1: Alkanes, alkenes, alkynes.
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, the number of grams of iodine absorbed by 100 g of fat or oil, to indicate the amount of unsaturated acids.

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16.2.4 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, e.g. 1-ethyl-2-methylcyclopropane.
Cyclopropane C3H6, colourless gas, former anaesthetic, petroleum odour, is easily ignited, may cause frostbite, containers may explode.
Cyclobutane C4H8, tetramethylene, condenses to liquid at 13^oC, insoluble in water, containers may explode.
Cyclopentane C5H10, pentametylene, colourless liquid, flash point -37^oC, is insoluble in water.
Cycloheptane C7H14, heptamethylene, colourless oily liquid, flash point 16^oC, narcotic effect
Cyclooctane C8H16, octamethylene

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16.2.6 Octadecan-1-ol, C18H38O
Octadecan-1-ol, stearyl alcohol, C18H38O, CH3(CH2)17OH, long-chain primary fatty alcohol
It is used for skin care, and occurs in Camellia sinensis.
Use octadecan-1-ol for melting point curve experiments.

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16.2.7 Octanol, CH3(CH2)7OH
or 1-Octanol, CH3(CH2)7OH, C8H18O, CH3(CH2)6CH2OH, CH3(CH2)5CH(OH)CH3, octyl alcohol, 1-octanol, n-octyl alcohol, octan-1-ol, caprylic alcohol, Flammable
3.10.0 Poisons and First Aid: See Octanol.

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16.3.1 Alkanes CnH2n+2, paraffins
Alkanes (paraffins): aliphatic hydrocarbons with only single bonds, i.e. just C-C, C-H single bonds
Alkanes, cyclohexane, heptane, hexane, liquefied petroleum gas (LPG), octane, pentane, petroleum spirit
Alkanes: methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane
The first 10 unbranched alkanes and molecular formula: methane CH4, ethane C2H6, propane CH3H8, butane CH4H10, 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^-, also "Me".
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 5-ethyl-3, 4-dimethyloctane.
Saturated hydrocarbons, e.g. hexane C6H14, all carbons have either four or three hydrogens bonded to them and no double bonds, triple bonds or rings, react in almost the same way.
Formation of alkanes:
* Hydrogenation of alkenes --> alkanes
CH2=CH2 + H2 --> CH3-CH3 (Pt catalyst)
ethylene + hydrogen --> ethane
CH3CH=CHCH3 + H2 --> CH3CH2CH2CH3 (Pt catalyst)
* Decarboxylation (remove CO2) from molecules that have -COOH group
RCOONa + NaOH --> R-H + Na2CO3 (dry distillation with soda lime)
CH3COONa + NaOH --> CH4 + Na2CO3

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16.3.3 Friedel-Crafts reaction
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^-

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16.3.5 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

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16.4.1Alkenes CnH2n, olefins
Alkenes (olefins): aliphatic hydrocarbons that contain one or more double bonds, i.e. dienes.
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 alkenes.
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 solution.
2. The cycloalkenes, cycloolefins, are closed chain, non-aromatic forms, e.g. cyclopropene CH.CH.CH2, cyclobutene, cyclopentene, cyclohexene.

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16.4.2 Prepare ethene
Ethylene (IUPAC name: ethene), hydrocarbon, formula C2H4 or H2C=CH2.
13.3.0: Prepare gases with gas generation apparatus
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 apparatus.
Be careful!
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
2H">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 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
4. Prepare ethene with ethanol, method 1.
See 3.96: Breakdown ethanol to ethene (ethylene).
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 rubber stopper.
Heat the flask to raise the temperature quickly to 170^oC, then control at 170^oC.
This heating procedure is used to increase the use ratio of ethanol and decrease by-products.
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 produced ethene.
C2H5OH (l) --> C2H4 (g) + H2O at 170^oC
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 test-tube.
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 170^oC, 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.

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16.4.3 Dienes, diolefins
Dienes are alkenes with two C double bonds in the molecule, CnH2n-2, (same formula as alkynes, so dienes are alkyne isomers).
Cumulated dienes have two C double bonds next to each other, e.g. 1,2-propadiene, H2C=C=CH2.
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.
Unconjugated dienes, have two double bonds separated by two or more single bonds.
Cyclodienes, 1.3-cyclohexadiene, 1.4-cyclohexadiene

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16.5.1 Arenes, benzene
See 16.3.4.0: 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 non-polar solvents.
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.

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16.5.3H Nitration
See 10.01.10: Liebig condenser
12.7.01 Nitration
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 group.
Experiment
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.

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16.6.1.0 Ethane, C2H6, CH3CH3
13.3.0: Prepare gases with gas generation apparatus
See diagram 16.1.1: Ethane
Ethane is a colourless and odourless gas, which has properties similar to methane.
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

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16.6.2.0, Propane, C3H8
Colourless liquefied petroleum gas, a bottled gas, BP -42.2^oC, catalytic cracking forms propylene, propellant, aerator, fuel for gas barbecue and blow torch

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16.6.4.0, Butane, C4H10
| See diagram 3.32: Collect insoluble gases over water, See 3.
| See diagram 16.1.2: Butane isomers.
n-Butane, BP -0.5^oC, RD 0.60 at 0^oC, is stored as liquid under pressure in steel cylinders giving Calor gas and cigarette lighter gas, (in cigarette lighters and portable gas appliances).
Butane is a Highly flammable gas at room temperature, vapour pressure 2.4 atm.
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.
Prepare butane
13.3.0: Prepare gases with gas generation apparatus
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
Combustion of butane
Butane / Oxygen combustion
2C4H10 + 13O2 --> 8CO2 + 10H2O + energy

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16.6.5.0 Pentane, C5H12
Pentane, BP 36.3^oC, RD 0.63, is made by distillation of petroleum.

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16.6.6.0 Hexane, C6H14
Hexane, BP 68.7^oC, RD 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.

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16.6.7.0 Heptane, C7H16
Heptane, BP 98^oC, RD 0.68, nine isomers, normal heptane has similar properties to normal hexane.

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16.7.9 Octane number
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.
Table 16.1.1h

Engine compression ratio	4: 1	5: 1	6: 1	7: 1	8: 1	9: 1	10: 1	11: 1	12: 1
Octane number to be knock-free	60	73	81	87	91	95	98	100	102

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16.1.2.3 Trienes
Trienes are alkenes with has three C double bonds, e.g. C6H8, (1,3,5-hexatriene).
Menthatriene, C10H14, p-Mentha-1,3,8-triene, para-menthatriene, terpene, camphor, woody aroma and taste, not used for fragrances of flavours, colourless-yellow liquid, roasted odour, parsley aroma, in Parsley, (Petroselinium crispum), Apiaceae, in Jesuit's tea, (Dysphania ambrosioides), Amaranthaceae

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16.7.0 Alkynes CnH2n-2, acetylenes
Alkynes (acetylenes): aliphatic hydrocarbons which have one or more triple bonds.
Alkyne, R1-CC-R2 (triple bond C≡C bond 6 electrons, e.g. acetylene, HC≡CH
Alkyne, Prefix: alkynl-, Suffix: -yne (no principal functional group), (acetylenes)
1. acetylenes: ethyne (acetylene) C2H2, HC≡CH, isoprene, methylene
Suffix: (-yne), for C≡C, (acetylenes), are unsaturated hydrocarbons with at least one triple bond (≡) between C atoms.
Alkynes decolorize acidified potassium permanganate solution and bromine solution.
2. The cycloalkynes are closed chain, non-aromatic forms, e.g. cyclooctyne C8H12, the smallest form.

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16.6.1 Alcohols
See diagram 16.0.1: Tetrahedral geometry of carbon, methane molecule, isobutyl alcohol
Alcohols, CnH2n+1OH, (ROH), (-ol), alkanols, the two simplest alkanols are methanol CH3OH, and ethanol C2H5OH.
The R in an alcohol formula is not specific.
Alkanol, a type of alcohol ROH, but R must be an alkane molecule.
Alkanol, aliphatic alcohol, alkyl alcohol, ROH (Prefix: hydroxy-), (Suffix: -ol) (-OH: alcohol)
Alcohols are organic compounds with the functional group -OH, but when -OH attached to an aromatic ring called phenols.
Alcohols, alcohols group: (-OH) Suffix: (ol)
Primary alcohols
Methanol, CH3OH
Butyl alcohol, butanol C4H9OH, 1-butanol, butan-1-ol, n-butyl alcohol, paint solvent, in hydraulic brake fluids
Secondary alcohols
propan-2-ol (CH3)2CHOH
2-butanol, butan-2-ol, sec-butanol, sec-butyl alcohol, CH3CHOHCH2CH3
Tertiary alcohols
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, e.g. R3COH.
The "hydroxyl" refers to the radical HO^-.
The "alcohol" in alcoholic beverages is ethanol, ethyl alcohol, CH3CH2OH.
Alkanol, CnH2n+2O

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16.6.2 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.
16.6.1Tests 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 agents.
(O)R1-CH(OH)-R2 --> R1-C(O)-R2(O)R-CH2OH --> R-CHO(O)R-CHO --> R-COOH
Allyl alcohol C3H6O, CH2CHCH2OH, 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 group (-OH).
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.

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16.6.3 Butanol. C4H9OH
"Butanol" butyl alcohol C4H9OH has 4 isomers: 1. n-butanol (1-butanol), 2. sec-butanol (2-butanol), 3.isobutanol (2-methylpropan-1-ol), 4. tert-butanol (2-methylpropanol). 1. Butan-1-ol, n-butanol, 1-butanol, n-butyl alcohol, butyl alcohol, primary alcohol), C4H9OH, n-propyl carbinol, (biobutanol), colourless liquid used in paint solvent, in hydraulic brake fluids, in organic chemical synthesis, plasticizers, detergents
2. Butan-2-ol, sec-butanol, 2-butanol, sec-butyl alcohol (secondary alcohol), C4H10O, secondary butanol, secondary butyl alcohol, s-butyl alcohol, product of grain and hops fermentation
3. Isobutanol, isobutyl alcohol, IBA, C4H10O, 2-methylpropan-1-ol, 2-methyl-1-propanol, additive to reduce viscosity, flavouring agent
4. Tert-butanol, t-butanol, tert-butyl alcohol,(TBA) (CH3)3COH, 2-methypropan-2-ol, 2-methyl-1-propanol, trimethyl carbinol
It is the simplest tertiary alcohol, so is often just called "butyl alcohol" or "butanol".
It has the hydroxyl on the same carbon with three methyl groups, used as a paint remover and solvent, Harmful by all routes, flammable.

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16.6.4 Butyl glycol
Butyl glycol C4H9OCH2CH2OH, 2-butoxyethanol, butyl cellosolve, butyl ether of ethylene glycol, in window cleaner "Windex", in inks, in paint, in solvents

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16.6.5 Dihydric alcohols, glycols
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, BP 197.5^oC, car radiator antifreeze, coolant, in hydraulic fluids, paint and plastic solvent, sweet taste, but poisonous
2. Butane-1,4-diol, C4H10O2, HO(CH2]4OH, tetramethylene glycol
CH2CH2 (oxidation) --> CH2OCH2 (+ water) --> HOCH2CH2CH2CH2OH
ethene (oxidation) --> epoxyethane (+ water) --> ethane-1,2-diol (glycol, antifreeze)
3. Propane-1,2 diol, propylene glycol, C3H8O2, CH3CHOHCH2OH, colourless, tasteless, odourless, solvent for pharmaceuticals

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16.6.6 Ethanol
Ethanol, ACS reagent, 99.5% (200 proof), absolute, ethyl alcohol, CH3CH2OH, C2H5OH, clear, colourless, mobile liquid, volatile organic compound, inflammable.
It has a 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, BP. -78.3^oC, absolute alcohol = 100% ethanol.
RD 0.79 gm cm^-3, BP. 78.5^oC, absorbs moisture from air.
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 abortion, developmental problems, or birth defects, "foetal alcohol syndrome".
Chronic ingestion of ethanol may cause liver cirrhosis and affect the nervous system.
Ethanol safety
Do not heat ethanol over an open flame, but use a water bath.
Ethanol may be used 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 oxidizing agents.
Ethanol with acidified dichromate solutions is highly exothermic.
Ethanol reacts violently with potassium.

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16.6.7/a> Fatty alcohols
Fatty alcohols are aliphatic alcohols from natural fats and oils in plants and animals.
They have an even number of carbon atoms.
The -OH group is attached to the terminal carbon.
They are amphipatic (having both polar (water-soluble) and nonpolar (not water-soluble) portions in the structure of the molecule,
so they can act as non-ionic surfactants.
Fatty alcohols are used in cosmetic formulations as emulsifiers, emollients and thickeners.
List of some fatty alcohols:
Butyl alcohol, C4H10O
Isoamyl alcohol, C5H12O
Capryl alcohol, 1-octanol, C8H18O, clear colourless liquid, aromatic odour, insoluble in water, floats on water, irritate eyes, nose.
Capric alcohol, 1-decanol, C10H22O, clear colourless liquid, sweet fat-like odour, insoluble in water.
Lauryl alcohol, 1-dodecanol), C12H26O, from coconut oil fatty acids, is tasteless and colourless, but has a flowery smell.
Cetyl alcohol, C16H34O
Cetostearyl alcohol, C34H72O2, waxy white solid, soapy odour, floats on water.
Stearyl alcohol, C18H38O : 16.6.8.1
Behenyl alcohol, C22H46O, 1-docosanol, alcohol, aliphatic alcohol, antiviral activity, topical treatment of recurrent herpes simplex (cold sores)
Ceryl alcohol, 1-hexacosanol, C26H54O, very long-chain primary fatty alcohol
Heptacosanol, 1-heptacosanol, C27H56O, very long-chain primary fatty alcohol
It occurs in Euphorbia granulata, and Sigesbeckia glabrescens.

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16.6.8H Methylated spirits
Methylated spirits (95% CH3CH2OH, 5% CH3OH), or absolute ethanol is usually denaturated with 4.8% methanol.
However, thet composition is legally different in different countries, e.g. Australia 2% methanol.
Methylated spirits, methylated ethanol, "spirits", "metho".
Methylated spirits is sold retail in Australia as 95% ethanol, UN 1170, duplicator fluid / duplicator spirit, Fordigraph spirit duplicator fluid
Denatured alcohol
Additional substances are used to "denature" the ethanol so it cannot be consumed However, it may be consumed by Aboriginal people in Australia by mixing methylated spirits with condensed milk.
The sugar derivative, sucrose octoacetate, in Thaumatin, from the West African plant Ketemfe (Thaumatococcus danielli), E 957, relative sweetness 750 to 1 600
It is bitter to raste and is used as a harmless denaturant for alcohol to make denatured spirit undrinkable.
Previously, denatured spirit contained methanol to make it undrinkable, but it caused blindness in alcoholics determined to drink it.
Use of methanol in home-made alcoholic beverages is illegal, because it may cause blindness.
Spirit vini meth (90% ethanol + 5% v/v methanol+ 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 + blue dye), (190-proof ethanol + 4% methanol + 1% other denaturants), (99% methylated spirits +1% bitrex)
Consumption of methylated spirits
Do not consume methylated spirits. If methylated spirits is swallowed, do NOT induce vomiting, because it may enter the lungs.
Flammability of methylated spirits
Methylated spirit is highly flammable and must not be used near naked flames.
It must be boiled in a beaker or 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 flames.
Heating methylated spirits
Use a water bath to heat methylated spirit in a flask, so if the flask cracks, a mixture of water and methylated spirit is less flammable than pure methylated spirit.
Handling methylated spirits
Repeated contact of the skin with methylated spirit can cause dermatitis, so wear rubber gloves if using methylated spirit as a solvent for cleaning.
Mixing methylated spirits
Do not mix methylated spirit with an oxidizing acid, e.g. concentrated nitric acid, because a vigorous reaction or explosion may occur.
Uses of methylated spirits
Use methylated spirit as a cheap low toxicity cleaning solvent for solvent extraction.
Observe the rapid changes in colour during the dissolution of plant pigments in methylated spirits.

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16.6.9 Naphthols
See diagram 16.1.4.3: Phenols, Quinones, naphthols.
See 12.11.5.7: Tests for carbonates, Molisch's test (α-naphthol test).
1-naphthol C10H7OH, a-naphthol, alpha-naphthol, naphthalen-1-ol, tests for carbonates.
2-naphthol C10H7OH, b-naphthol, beta-naphthol, naphthalen-2-ol, white solid, antioxidant in rubber products, antiseptic, tests for primary amines.

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16.6.10 Nitroglycerine
Nitroglycerine (UK), Nitroglycerin (USA), C3H5N3O9, ester of nitric acid
glycerol + cold mixture of concentrated sulfuric acid + nitric acid --> C3H5N3O9
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 shock.
It freezes at 13^oC, 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.

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16.6.11 Nitrocellulose, gun cotton
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.

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16.6.12 Phenols
Phenols, group: (OH-C), in a benzene ring, Phenol = C6H5O6
See diagram 16.1.4.3: Phenols, quinones, naphthols, coniferyl alcohol (p-coumaryl alcohol), urushiol, organohalogens.
9.4.1.05 Vitamin E
3.85 Antioxidants, vitamin E
3.9.9 Free radicals and antioxidants
3.9.7: Cholesterol C27H46O
1. Phenols, Ar-OH, are compounds with an hydroxyl group, -OH, is firmly attached to an aromatic ring, e.g. benzene, 2-naphthol, benzene-OH, hydroxybenzenes.
Phenols, group: (OH-C), in a benzene ring, Phenol = C6H5O6: 16.6.12
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, C6H2Br3OH.
Chlorophenol red, C19H12Cl2O5S, (acid-base indicator):
../chemistry/UNChemAcidbase.html#9.0H">9.0
PLA synthetic fibre, polylactic acid, polylactide

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16.6.13 Propanol, C3H7OH
Propanol C3H7OH has two isomers:.
1. Propan-1-ol, 1-propanol (n-propyl alcohol) C3H8O, CH3CH2CH2OH, Highly flammable, Toxic if ingested
2. Propan-2-ol, 2-propanol (iso-propyl alcohol) C3H8O, CH3CH(OH)CH3, C3H7OH, sec-propyl alcohol, rubbing alcohol, Flammable
Potassium dichromate as an oxidizing agent:.
propan-2-ol + potassium dichromate (VI) solution + dilute sulfuric acid --> water + propanone (acetone) ketone
CH3CHOHCH + O (from oxidizing agent) --> (CH3)2CO + H2O

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16.6.14 Pyrogallol
Pyrogallol, (1,2,3-trihydroxybenzene), C6H6O3, C6H3(OH)3, white crystals, reducing agent, alkaline solution,br> (use sodium hydrogen carbonate, not sodium hydroxide), reacts with oxygen in the air to form a brown polymer,
used where oxygen must be eliminated from a gas or from the air, highly toxic if ingested, corrosive to skin.
Pyrogallol is prepared by heating Gallic acid.
Germination and air: 9.118.
Test gas collected in a respirometer: 6.6.12.
Toxicity, Poisons and First Aid: 3.10.0

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16.6.15 Resorcinol
See diagram 1.3.2.3: 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, benzene-1-3-diol, benzene-1-3-diol, 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 fluorescein dyes.
Resorcinol C6H6O2, argan oil, in Argania spinosa.
Prepare formaldehyde resorcinol resin: 3.4.6.1.
Resorcinol, Xanthene dyes: 7.9.56.1.

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16.6.16 Prepare sodium ethoxide
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.

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16.6.17 Triclosan
See diagram 1.3.2.3: Triclosan.
Triclosan, TCS, 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.

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16.6.18 Trihydric alcohols, glycerol
The trihydric alcohols, have three hydroxyl groups on different carbon atoms, e.g. glycerol C3H8O3.

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16.9.1 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.

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16.9.2 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.

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16.9.3 Methyl mercaptan
Methyl mercaptan, methanethiol, methyl mercaptan, "captan", CH3SH, CH4S, (MeSH), simplest thiol, an alkanethiol, colourless gas, low-boiling liquid, denser than water, very toxic by inhalation, can be absorbed through the skin, highly flammable, liquid burns causes frostbite
It has a sharp putrid odour, but the sense of smell cannot be relied upon to warn of the presence of vapours at low concentrations, odour threshold 0.002 ppm
It comes from from decayed organic matter, pulp mills, oil refineries; It has an offensive rotten cabbage or decomposing vegetables smell, as in bad breath and flatus.
It occurs in some nuts and cheese, in blood, brain, and other tissues of people and animals.
It is released from animal faeces released from decaying organic matter in marshes and as decay product of wood in pulp mills.
It occurs in the natural gas of certain regions, in coal tar, in some crude oils, and is manufactured for plastics industry, pesticides, jet fuel additive.

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16.9.4 Thiols (Mercaptans)
See diagram 16.1.4.3 : Thiophenol (phenyl mercaptan)
See diagram 16.1.4.3 : Thiophenol (phenyl mercaptan) See diagram 16.13.10: Thiols, Metam, zineb.
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,-Na⁺).
Thiols, RS-H, are oxidized to disulfides, RS-SR.

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16.1.3.4 Ethers
See: 1.13 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. "ether".
Ethers (ROR'), CnH2n+2O), alkyl ethers, ethoxyethane ether, e.g. dimethyl ether CH3OCH3.

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16.1.3.5 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.

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16.1.3.7 Benzoyl
Benzoyl group, benzene carbonyl group C6H5CO-, e.g. benzoyl chloride C6H5COCl.

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16.1.3.8 Acetal
Acetal, 1,1-diethoxyethane, Diethyl acetal, Acetaldehyde diethyl acetal, C6H14O2, clear colourless liquid, pleasant odour, slightly soluble in water, toxic, narcotic in high concentrations, in garden onion, flavouring ingredient in fruit, rum, whisky.

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16.7.10 Organic salts
Organic salts, e.g. sodium ethanoate (sodium acetate) CH3COONa, ammonium acetate CH3COONH4.
NaHCO3 + CH3COOH --> CH3COONa + H2O + CO2 (g).

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16.7.16Saturated hydrocarbons
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.

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16.1.5.5 Acyl halide
Acyl halide, acid chloride, Acid chlorides group: (-COCL), Suffix: -oyl chloride.
Acyl chloride (RCOCl), e.g. ethanoyl chloride (Acetyl chloride, CH3COCl).

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16.1.5.6 Amides
Amides, acid amides (-amide) (amide group: -CONH2, RCONH2
Suffix: -amide, e.g. urea, H2NC=ONH2
[IUPAC says: 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, CH3CONHCH2CH3, N.N-dimethylmethanamide HCON(CH3)2
(the polymer group -CO-NH-)
inorganic amides, e.g. KNH2.

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16.1.5.6a Carbamates
See diagram 16.13.7: Carbamates, carbaryl, methiocarb.
The carbamate ion, CH2NO2-, is a derivatives of carbamic acid, NH2COOH, H2NC(=O)OH
Carbamates are esters of carbamic acid, CH2NO2-, NH2COOH,
Carbamate esters are called urethanes. A urethane, C3H7NO2, NH2COOC2H5 is the ethyl ester of carbamic acid and is found in alcoholic beverages ethanol + carbamic acid --> urethane Urethanes are esters of carbamic acid, i.e. alkyl carbamates.
Polymers that include repeating carbamate units, -NH (CO)O-. are called polyurethanes
Polyurethanes are derived from the polymerization of isocyanates. Examples of carbamates: carbamic acid, ammonium carbamate, bendiocarb, carbaryl, 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.
Carbamates, carbamate R-O (C=O)N-R,R, 16.1.5.6a
See diagram 16.13.7 Carbamates, carbaryl, methiocarb
See diagram 16.13.8 Deet, DMP dimethylphthalate
Amides, 16.1.5.6
Ammonium carbonate, smelling salts, 12.16.3.5
Carbamide (urea), CO(NH2)2, CO(NH2)2
Carbazole C12H9N
Deet, N,N-Diethyl-meta-toluamide, C12H17NO
Ethyl carbamate, C3H7NO2, blood flow in a fish, 9.217
Ethyl carbamate, Urethane, carbamate esters, 7.9.54.2
Mancozeb (fungicide), 4.6.14
Maneb (fungicide), 4.6.13
Organophosphate and carbamate insecticides, 4.5b Organophosphate and carbamate insecticides
Thiocarbamate R-O (C=S)N-R, R
Urea CO(NH2)2
Urethane carbamate esters = urethanes, R2NC(=O)OR', where R' not = H, R= ethyl

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16.1.5.6.1 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.
Polyacrylamides: 3.7.3.0.
Acrylamide, C3H5NO, CH2CHCONH2, is the amide of acrylic acid, propenoic acid CH2CHCOOH, an unsaturated liquid carboxylic acid.
Acrylamide is a poison, harmful if swallowed, inhaled or absorbed through skin, affects central and peripheral nervous systems and reproductive system.
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.

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16.1.5.7 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.

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16.7.2 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.

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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.

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Mineral oil
Mineral oil, low value byproduct of petroleum distillation, usually 15^oC to 40^o C, many uses, lubricating light oil.

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Hydraulic fluid
Hydraulic fluid, mineral oil with low compressibility, needs correct viscosity for different machines.

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16.1.13 Prepare triodomethane (iodoform)
See 1.6: Tests for starch, iodine solution, Add five drops of iodine solution to five drops of ethanol.
Add drops of dilute sodium hydroxide solution until the brown colour of iodine disappears.
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).

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16.1.14
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.
It is prepared by passing chlorine gas through a calcium hydroxide solution.
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 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 + oxygen --> 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).

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16.1.14.1 Reaction of acetone with bleaching powder
CH3COCH3 + 3Cl2 --> CCl3COCH3 + 3HCl.
2CCl3COCH3 + Ca(OH)2 --> 2CHCl3 + CH3COO)2Ca.
Ca(OH)2 + 2HCl --> CaCl2 + 2H2O.

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16.1.14.2 Reaction of ethyl alcohol with bleaching powder
C2H5OH (l) + Cl2 (g) --> CH3CHO (l) + 2HCl (aq).
ethyl alcohol + chlorine --> ethyl aldehyde + hydrochloric acid.
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 55^oC.
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.

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16.7.11 Organometal compounds
(prefix the metal with organo-, e.g. organomagnesium compounds.
MeMgI iodo(methyl)magnesium, Et2Mg diethylmagnesium.

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16.2.3.1 Carbides, C^4-
Carbide are binary compounds of:.
1. C + electropositive element, e.g. calcium carbide, CaC2.
2. C + heavy metal, for cutting tools, e.g. aluminium carbide, Al4C3, chromium carbide, Cr3C2, iron carbide Fe3C (cementite).
Tungsten carbide ("carbide", WC), is used for cutting tools, milling tools, abrasives, jewellery.
Iron carbide is formed with carbon monoxide when iron oxide is heated with charcoal.
3Fe2O3 +11C --> 2Fe3C + 9CO (g).
Types of carbides:
Methanides
1. Methanides, e.g. aluminium carbide, Al4C3
Hydrocarbyl anions, methyl anion, conjugate base of methane.
Methanides + water --> methane.
Al4C3 + H2O --> Al(OH)3 + CH4
2. Acetylides, e.g. calcium carbide, CaC2
Acetylides, salts of acetylide anion, C2^2-, (percarbide).
Acetylides are formed by alkali metals, alkaline earth metals, lanthanoid metals, e.g. sodium carbide Na2C2, lanthanum carbide LaC2, aluminium carbide Al4C3, iron carbide (cementite) Fe3C.
Acetylides (percarbides), C2^2- + water --> acetylene.
Sodium acetylide C2HNa, Copper (I) acetylide Cu2C2.
Calcium acetylide CaC2 is commonly called calcium carbide.
Calcium carbide CaC2 (calcium dicarbide, "carbide", calcium acetylide, acetylenogen, ethnide dicarbide, Toxic by all routes.
CaC2 + 2H2O --> C2H2 + Ca(OH)2.
calcium carbide + water --> acetylene + calcium hydroxide.

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Sesquicarbides
Sesquicarbides, e.g. magnesium carbide, Mg2C3
C3^4-.
Mg2C3 + H2O --> Mg(OH)2 + C3H4.
magnesium carbide + water --> magnesium hydroxide + propyne (methylacetylene, CH3C≡CH.

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Covalent carbides
Covalent carbides, Boron carbide B4C, very hard material, is used in armour.
Silicon carbide, SiC (carborundum), abrasive, moissanite synthetic gemstone, emery paper, sanding paper, sharpening stone, fine particles, Toxic by inhalation.

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16.7.6 Nitriles
Organic compounds containing the −C≡N group are called nitriles.
Inorganic compounds containing the −C≡N group are called cyanides.
Nitrile.
Nitriles (acid nitriles, alkyl cyanides, cyanides), (−C≡N, R-C≡N) (note triple bond), Cyanide ion: CN- e.g. ethane nitrile, Ascetonitrile (methyl cyanide) CH3CN, 5-methoxyhexanenitrile, CH3C(OCH3)HCH2CH2CH2CN.
Acrylonitrile is used for making Orlon (vinyl cyanide, 1-cyanoethene) CH2=CH-CN.
A cyanide contains the cyano group C≡N.

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16.7.6.1 Cyanamides
Cyanamides (inorganic, CN2^2-), ionization reaction of methylamine.
See diagram 16.7.6.1: 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 (HCN).
CaCn2 + H2O + CO2 --> H2NCN + CaCO3.
calcium cyanamide + water + carbon dioxide --> cyanamide + calcium carbonate.
(NH2)2CO --> HCNO + NH3.
urea --> cyanic acid + ammonia.
6HCNO --> C3H6N6 + 3CO2 (polymerization reaction).
cyanic acid --> melamine + carbon dioxide.
6(NH2)CO --> C3H6N6 + 6NH3 + 3CO2.
Melamine, C3H6N6, (2,4,6-triamino-1.3,5-triazine) is 66% nitrogen w/w and is used in the plastics industry.
Its high nitrogen content has been the reason for its illegal use as powdered milk pollutant in China, causing death and kidney problems in young babies due to the formation of kidney stones.
Melamine-formaldehyde (MF), 4H6N6O, hard to ignite, alkaline fumes, burns with pale yellow flame (light blue-green edge), formaldehyde and fish-like smell, thermosetting plastic, it retains strength and shape on heating.
Melamine crockery is sold as being green, virtually unbreakable, dishwasher safe, Not suitable for microwave oven.

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16.2.4.3.0 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, phenylamine
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

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16.7.4 Methylamine ionization reaction
CH3NH2 + H2O <--> CH6N+ and OH-
methylamine + water <--> methylammonium ion + hydroxide ion

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16.7.15 Phenylamine
Prepare phenylamine
1. Benzene + concentrated nitric acid + concentrated sulfuric acid --> nitrobenzene, C6H5NO2
2. Nitrobenzene + tin catalyst Sn + reducing agent hydrochloric acid --> phenylamine + water
C6H5NO2 + 6 H⁺ --> C6H5NH2 + 2H2O

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16.7.5 Nitrosamines
Nitrosamines produced by reaction of nitrous acid with secondary amines and can be formed in the gut if nitrites react with amino acids.
C4 explosive, detonator, solid rocket propellant, mainly cyclonite or cyclotrimethylene trinitramine.
RDX explosive (Research Department Explosive, (O2NNCH2)3, Cyclonite, Hexagen, used against German submarines during World War II.

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16.2.4.3.05 Clenbuterol, C12H18Cl2N2O
Performancing-enhancing drug banned by the International Olympic Committee, illegally used to build skeletal muscle and increase metabolism, but may cause heart attacks, substituted phenylaminoethanol with beta-2 adrenomimetic properties at very low doses, used as a bronchodilator in asthma treatment.
Approved for use in some countries, as at 2006 not an ingredient of any therapeutic drug approved by the USFDA.

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16.2.4.3.1 Ethylenediamine
ClCH2CH2Cl + 4 NH3 --> H2NCH2CH2NH2 + 2 NH4Cl.
1,2-dichloroethane + ammonia --> ethylenediamine + ammonium chloride.

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16.7.3 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)

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16.7.1 Cyclic imines
Pyrrolines
Pyrrolines (dihydropyrroles), three compounds differ in position of double bond, 1-Pyrroline cyclic imine C4H7N, 2-pyrroline and 3-pyrroline cyclic amines
2-Acetyl-1-pyrroline C6H9NO, bread smell

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16.7.8 Nitroalkanes
Nitroalkanes (nitroparaffins) CnH2n+1NO2)
Nitromethane CH3NO2, nitroethane C2H5NO2, urea (carbamide) CH4N2O

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16.7.7 Nitrites
Nitrites (NO2-), dioxonitrate ion, salts or esters of nitrous acid, HNO2, (O=NOH)
Nitrites group: -C=N, Suffix: -nitrite, e.g. sodium nitrite NaNO2, potassium nitrite KNO2, used as meat curing agents.

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16.2.4.7 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
Chemical suppliers: Ethyl 2-cyanoacrylate, liquid, C6H7NO2
GBL, γ-butyrolactone is a naturally occurring colourless oily liquid with a characteristic odour.
It is used as a stain remover and stripper, (including "Superglue").

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16.2.5.1 Azide compounds
Azide compounds, (N3^-), or (-N3), (-N=N⁺N-), is usually attached to carbon, e.g. Phenyl azide (azidobenzene) C6H5N3.
Diazine(diimide) (HN=NH)
Also, salts of hydrazoic acid, HN3, e.g. sodium azide NaN3

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16.2.5.2 Azo compounds
Azo compounds: derivatives of diazene (diimine, diimide), H2N2, HN=NH, with both hydrogens substituted by hydrocarbyl groups,
e.g. azobenzene or diphenyldiazene (PhN=NPh)
Hydrazone (ketone + hydrazine (N2H4) - water), (RC=NNH2R')
3.0, See: 3.0 Benzopurpurin.

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16.2.5.3 Diazo compounds
Diazonium ion R-N⁺N, diazonium compounds [(RNN⁺) Cl^-], e.g. diazomethane, CH2N2
HNO2 and HCl + R-NH2 --> R-N⁺N + Cl^-
nitrous acid and hydrochloric acid + amines --> diazonium ion + chloride ion
HNO2 + HCl + C6H5NH2 --> C6H5N2Cl + 2H2O
nitrous acid + 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.

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16.7.14 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, paraquat
1. Phosphonic acid, phosphorous acid, H3PO3
2. Phosphonoglycine
16.7.3 Glyphosate, herbicide
3. Organic phosphates: acephate, diazinon, dichlorvos, dimethoate
malathion (maldison), naled, parathion
16.11.0 Isothiocyanates

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16.11.0 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

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16.11.1 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, (Brassica nigra), Brassicaceae
Horseradish, (Armoracia rusticana), Brassicaceae
Wasabi, (Wasabi japonica), Brassicaceae

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16.11.2 Benzyl isothiocyanate
Benzyl isothiocyanate, (BITC), C6H5CH2NCS, C6H5CH2NCS, benyl mustard oil, isothiocyanotaometylbenzene, in cruciferous vegetables, possibly anti-cancer, apotosis, anthelmintic in Papaya seeds

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16.11.3 Ethyl isothiocyanate
Ethyl isothiocyanate, CH3CH2NCS, ethyl mustard oil
Fluorescein isothiocyanate, (FITC), C21H11NO5S.

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16.11.4 Methyl isothiocyanate, (MITC), CH3NCS, soil fumigant, toxic, corrosive, active ingredient in pesticide Metam

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16.11.5 Phenethyl isothiocyanate
Phenethyl isothiocyanate (PEITC), C9H9NS, in cruciferous vegetables, watercress, possibly anti-prostate cancer

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16.11.6 Phenyl isothiocyanate
Phenyl isothiocyanate, C6H5NCS, (PITC), Edman's reagent, isothiocyanatobenzene, colourless liquid, pungent odour, used for amino acids research to sequence peptides.
16.10.7 Methanethiol from asparagus

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16.10.10 Sulfides
Sulfides: RSR, (R not equal to H), (old name: thioethers)
1. 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 (sulfilimines): (H2S=NH).
2. Diallyl sulfide, from boiled cabbage
3. Disulfides from crushed garlic
See: Asparagus, (Asparagus officinalis, var. Mary Washington), garden asparagus

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16.8.1 Diesel oil
Diesel oil, gas oil or diesel distillate, diesel fuel, heating oil.
Mix of C15H32 to C18H38, 2 or more carbon atoms, alkanes, boiling range 250^oC to 350^oC.

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16.8.2 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, waxes).

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16.8.3 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 175^oC to 325^oC.

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16.8.4 Lubricating oil, motor oil, grease
Mix of C16H34 to C24H50, 20 to 50 carbon atoms, alkanes and cycloalkanes and aromatics, boiling range 300^oC to 370^oC.

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16.8.5 Naphtha
Naphtha (petroleum naphtha, ligroin), processed to make gasoline.
Mix of 5 to 9 carbon atoms, mainly aliphatic, e.g. alkanes, boiling range 120^oC to 180^oC, or < 200^oC.
The light hydrocarbon cut between gasoline and kerosene.
(Another naphtha can also be produced from coal tar.).

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16.8.6 Paraffin wax, heavy gas, fuel oil
Mix of C20H42 and higher hydrocarbons, 20 to 70 carbon atoms, alkanes and cycloalkanes and aromatics, boiling range 370^oC to 600^oC.

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16.8.7 Petrol
Petrol, "gas", gasoline, motor fuel
Mix of C6H14 to C11H24, 5 to 12 carbon atoms, alkanes and cycloalkanes, boiling range 40 to 205^oC.

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16.8.8 Petroleum gas (methane, ethane, propane, butane) Mix of 1 to 4 carbon atoms, boiling range < 40^oC.
Liquefied under pressure as LPG (liquefied petroleum gas), a mixture mainly of propane C3H8, and butane C4H10.

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16.8.9 Residuals
Residuals, bitumen, "tar", asphalt, waxes
A mix of C24H50 and higher hydrocarbons, multiple-ringed compounds, 70 or more carbon atoms, boiling range > 600^oC.
Petroleum jelly is a saturated semi-solid of crystalline and liquid hydrocarbons, carbon numbers < C25, made by dewaxing paraffinic residual oil.
Naphtha, (Greek naptha fire), was an inflammable bituminous substance used in warfare.

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16.10.1 Allicin
Allicin, C6H10OS2, Sulfoxide, Diallyl thiosulfinate, Diallyldisulfid-S-oxide, (Thio-2-propene-1-sulfinic acid S-allyl ester), produce by crushing garlic, unstable antioxidant, colourless liquid, distinctively pungent smell, botanical anti-fungal agent, antibacterial agent, used to treat follicular lymphoma, (FL)< in onion, in garlic, in Alliaceae species, causes smell of fresh garlic.
See diagram 16.2.8.2 : Allicin

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16.10.2 Alliin
Alliin, (S-allylcysteine), (3-(Allylsulphinyl)-L-alanine), ACSO, C6H11NO3S, Sulfoxide may cause respiratory irritation, in fresh garlic produced from Cysteine.

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16.10.3 Diallyl sulfide
Diallyl sulfide, C6H10S, organic sulfide, Allyl sulfide, Di-2-propenyl sulfide, Thioallyl ether, oil garlic, formed by hydrolysis decomposition of cabbage, flavouring ingredient, garlic odour, irritates eyes and skin, in animal foods, in Allium species, in Japanese horseradish Wasabia japonica, in black mustard powder Brassica nigra, used in cooked beef, possibly anti-cancer.

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16.10.4 Diallyl disulfide
Diallyl disulfide, C6H10S2, Organic Disulfide, Allyl disulfide, in Alliaceae species, insecticidal, antineoplastic, antifungal soil treatment, health benefits for most people, but some people are allergic to it, in garlic Allium sativum, in onion Allium cepa, in most Allium species.

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16.10.5 Diallyl trisulfide
Diallyl trisulfide, Organic Trisulfide, (DATS), Allitridin, S(SCH2CH=CH2)2, di-2-propenyl trisulfide, flavouring, used to treat high blood pressure, high cholesterol, circulatory diseases, antifungal, antitumour, antioxidant, apoptosis inducer, estrogen receptor antagonist, antineoplastic, vasodilator, antioxidant, anti-inflammatory, insecticide, antiprotozoal, platelet aggregation inhibitor, in traditional Chinese medicine, in garden onion (Allium sativum), in garlic oil essential oil from Allium sativum cloves.

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16.10.7 Methanethiol from asparagus
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.
See: Asparagus, (Asparagus officinalis, var. Mary Washington), garden asparagus

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16.10.8 Phenothiazine, PTZ, C12H9NS
11.12.0 Tranquillizers 1, major tranquillizers.
See diagram: 14.05, Phenothiazine C12H9NS.
Phenothiazine, light green powder turns green-blue in sunlight, psychoactive drug, antiemetic, antihistaminic, anticholinergic, prevents emesis.

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16.10.9 Siloxanes
Saturated silicon-oxygen hydrides with chains of alternating silicon and oxygen atoms, e.g. unbranched H3Si(OSiH2)nOSiH3, branched H3Si(OSiH2)nOSiH(OSiH2OSiH3)2
"Volasil" is octamethylcyclotetrasiloxane.
Dimethylpolysiloxane is an anti-caking agent, emulsifier and anti-foaming agent.

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16.10.11 Sulfonium compounds
Sulfonium compounds: [SR3]+, three organic substituents attached to sulfur
Sulfonium salts, e.g. Trimethylsulfonium chloride CH3)3SCl
Cyclopropyldiphenylsulfonium tetrafluoroborate, C3H5S(C6H5)2BF4
Tris(dimethylamino)sulfonium difluorotrimethylsilicate [(CH3)2N)3S]+[F2Si(CH3)3]−, fluoridation agent

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16.10.12 Sulfoxide
Sulfoxide, RS(=O)R', contains a sulfinyl, SO, functional group Alliin, L-alliin, sulfoxide in fresh garlic
Alliin, L-Alliin, C6H11NO3S, S-Allyl-L-cysteine sulfoxide, SAC, aroma of garlic
Dimethyl sulfoxide, DMSO, C2H6OS, from wood pulp, oyster garlic taste, (irritant, penetrates skin, horse liniment, anti-inflammatory, paint stripper, colourless
It is a common solvent and gives garlic taste after skin contact.
Propanethial S-oxide, syn-propanethial S-oxide, (1-sulfinylpropane), C3H6OS, a sulfoxide, a thiocarbonyl S-oxide, volatile liquid, lachrymatory factor
It occurs in sliced Onion, (Allium cepa), Amaryllidaceae.
Broken onion cells --> allinase enzymes + amino acid sulfoxides --> 1-propene sulfenic acid.
Then + lachrymatary factor synthesise enzyme (LFS) --> syn-Propanethial -S-oxide, a lacrimator.
In contact with water in the eye, the lacrimator hydrolyses to propanol, sulfuric acid and hydrogen sulfide, which stings the eyes.
It is relieved by tears from the tear glands.

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16.10.13 Thiocyanates
Thiocyanates: SCN−, Salts and esters of thiocyanic acid, HSCN, e.g. methyl thiocyanate C2H3NS

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16.10.14 Thiophene
Thiophene, thiolane, THT, CH2)4S, tetrahydrothiophene, colourless, unpleasant odour gas, used as odorant in natural gas and LPG gas (not in USA).

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16.6.19 Tests for hydrogen gas:
Na (s) + 2(C2H5OH) (l) --> 2(C2H5ONa) (s) + H2 (g)
sodium + ethanol --> sodium ethoxide + hydrogen
Evaporate the sodium ethoxide solution to form white crystals.
Add drops of water and test for litmus that turns blue.

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