III. Isomers - compounds with the same molecular formula that have different structural arrangements. A. The simplest alkane that can have isomers is butane, with a molecular formula of C 4 H 10 : structural formula ball and stick normal-butane aka n-butane isobutane aka i-butane

Isobutane as a gas for refrigeration systems, especially in domestic refrigerators and freezers, and as a propellant in aerosol sprays. When used as a refrigerant or a propellant, isobutane is also known as R- 600a. Some portable camp stoves use a mixture of isobutane with propane, usually 80:20. Isobutane is used as a feedstock in the petrochemical industry, for refrigerationrefrigerators freezerspropellant aerosol sprays refrigerantpropanepetrochemical Butane gas is sold bottled as a fuel for cooking and camping. When blended with propane and other hydrocarbons, it is referred to commercially as LPG. It is also used as a petrol component, as a feedstock for the production of base petrochemicals in steam cracking, as fuel for cigarette lighters and as a propellant in aerosol sprays such as deodorants.propane LPG lighterspropellant aerosol sprays deodorants n-butane i-butane

n-butane: b.p. = C i-butane: b.p. = C B.Isomers have different chemical and physical properties. Ex. Which isomer of butane has a higher boiling point? C.As the number of carbon atoms increases, the number of possible isomers increases. This is one reason why there are so many organic compounds. Ex.butane (C 4 H 10 ) has 2 isomers octane (C 8 H 18 ) has 18 isomers decane (C 10 H 22 ) has 75 isomers

ibuprofen is made of 2 isomers:

What do these have in common?

V.Functional Groups Many new organic compounds are formed when atoms other than C and H replace H in a hydrocarbon. These atoms or groups of atoms are called functional groups. The unchanged part of the remaining hydrocarbon is shown with an R: R rest of the hydrocarbon functional group goes here Each type of functional group produces a unique class (type) of compound and gives the compound distinct chemical and physical properties. bond

A. Halides Functional group: F, Cl, Br, I When the halogens (F, Cl, Br, I) replace a H atom in a hydrocarbon, the compound is called an organic halide or halocarbon. Ex. Take methane CH 4 and replace an H with a Cl It was used as a refrigerant and is now used to make polymers. formula: methane  becomes Cl CH 3 Cl

PVC = polyvinylchlorides: ethylene + chlorene = chloroethylene

PVC products

9000 shellfish to produce 1 gram of Tyrolian purple Rubens: The discovery of Tyrolian purple

PCBs Uses: plasticisersplasticisers in paints and cements casting agents fire retardantfire retardant fabric treatments and heat stabilizing additives for PVC electrical insulationheat stabilizing additives adhesives paints and water-proofing railway sleepers capacitors insulating fluids in transformers vacuum pumpvacuum pump fluids hydraulic fluids Between approximately 1947 and 1977, GE released up to 1,300,000 pounds (590,000 kg) of PCBs into the Hudson RiverHudson River Polychlorinated biphenyl T O X I C

A brominated flame retardant. It consists of twelve carbon, eighteen hydrogen, and six bromine atoms tied to the ring. Its primary application is in polystyrene foam that is used as thermal insulation in the building industry. Other uses are upholstered furniture, automobile interior textiles, car cushions and insulation blocks in trucks, packaging material, video cassette recorder housing and electric and electronic equipment.brominated flame retardantcarbonhydrogen bromine polystyrene 1,2,5,6,9,10-Hexabromocyclododecane T O X I C

Brominated Fire Retandants: T O X I C

Ex. Chloroform. Used to be used as an anesthetic, but is toxic. Now used as a solvent and to produce dyes and pesticides. Replace 3 H’s with Cl’s. methane  becomes Cl | Cl | Cl H— C—

Ex. CFCs (chlorofluorocarbons) cause the ozone layer to be destroyed. methane  Freon-22

CFCs

DDT: dichlorodiphenyltrichloroethane T O X I C C C

Polytetrafluoroethylene: Teflon T O X I C

B.Alcohols  R—____ Functional Group = ___________ group = OH The OH group makes alcohols polar. Alcohols dissolve in water because H 2 O is polar: Alcohol names all end in –___. Start with: H O H OH Replace an H with an -___ group: Ex: End up with: H H H C H ____________ H H H C __________ or methyl alcohol OH hydroxyl ol methane OH CH 3 OH

Ex. __________ (ethyl alcohol) = drug, solvent, fuel H H H C H H C H ___________ ________ or ethyl alcohol Replace an H with an -OH group: H H H C H H C Ex. __________ alcohol (rubbing alcohol) H H H C H H C H ___________ _________ or Isopropyl alcohol Replace a _________ H with an -OH group: H H C H H H C H C H H H C ethanol ethane OH CH 3 CH 2 OH isopropyl propane middle OH CH 3 CHOHCH 3

ethylene glycol Ethylene glycol is widely used as an automotive antifreeze and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet- tasting liquid. Ethylene glycol is toxic, and ingestion can result in death. OHOH OHOH H H C H C H

Glycerin (glycerol): --> clear, sweet tasting, oily liquid --> used to keep dried fruits and pastry fillings moist, in toothpaste, hand creams, eye and ear drops, suppositories (for laxatives, eg), and as an antifreeze H 2 SO 4 for drying aka nitroglycerin (dynamite) Also: glycerin + nitric acid --> glycerol trinitrate