Chapter 23

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Chapter 23. Organic Chemistry. Mr. Watson. HST. Methane. Butanes. Cycloalkanes. Gasoline-Knocking. Internal Combustion Engine. Box 8.2, pg. 285 Text C 9 H 20(l) + 14O 2(g) ---> 9CO 2(g) + 10H 2 O (g). CH 3 CH 3 | | CH 3 - C - CH 2 - CH - CH 3 - PowerPoint PPT Presentation

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Chapter 23Chapter 23

Organic Chemistry

Mr. Watson HST

Mr. Watson HST

Mr. Watson HST

MethaneMethane

Mr. Watson HST

ButanesButanes

Mr. Watson HST

CycloalkanesCycloalkanes

Mr. Watson HST

Gasoline-KnockingGasoline-Knocking

Mr. Watson HST

Mr. Watson HST

Internal Combustion EngineInternal Combustion EngineBox 8.2, pg. 285 Text

C9H20(l) + 14O2(g) ---> 9CO2(g) + 10H2O(g)

CH3 CH3 | |CH3 - C - CH2 - CH - CH3 | CH3 isooctaneoctane number = 100

CH3- CH2- CH2- CH2- CH2- CH2- CH3

n-heptaneoctane number = 0

Mr. Watson HST

Octane RatingOctane Rating

(R+M)/2R - RON - research octane number,

indicates the quality of the fuel used under normal driving conditions. The car is driving on level ground ~ 45 miles/hour. The RON engine is operating at 600 RPMs with normal carboration.

Mr. Watson HST

Octane RatingOctane Rating(R+M)/2

M - MON - MON testing uses a similar test engine to that used in RON testing, but with a preheated fuel mixture, a higher engine speed, and variable ignition timing to further stress the fuel's knock resistance. Depending on the composition of the fuel, the MON of a modern gasoline will be about 8 to 10 points lower than the RON.

Mr. Watson HST

Octane RatingOctane Rating

(R+M)/2engine is operated under test conditionsdegree of knocking determinedfuel is then blended from n-heptane and

isooctane to duplicate conditionspercentages measured, 87% isooctane, 87

octane gasoline

Mr. Watson HST

Oxygenated & Reformulated Oxygenated & Reformulated GasolinesGasolines

Oxygenated Gasolines – gasoline blends with organic compunds that contain oxygen, such as MTBE, methanol, ethanol, and tert-butyl alcohol

Reformulated Gasolines – oxygenated gasolines that contain lower percentage of aromatic hydrocarbons and have a lower volatility than ordinary gasoline

Mr. Watson HST

Catalytic CrackingCatalytic Cracking

A process that uses a catalyst, heat, and pressure to break long-chain hydrocarbons into shorter-chain hydrocarbons including both alkanes and alkenes, many in the gasoline boiling point range

Alkenes have higher octane numbers than corresponding alkanes

Mr. Watson HST

EthyleneEthylene

Mr. Watson HST

Mr. Watson HST

Addition PolymerAddition Polymerpolymer formed by joining many molecules

of the same compound to form the large molecule

The compound usually contains a carbon-carbon double bond

Mr. Watson HST

Condensation PolymerCondensation Polymerpolymer formed by molecules of two

different compounds joining to form the large molecule

one compound usually has an amine functional group

other molecule has carboxylic acid functional group

split out water molecule to form peptide linkage

Mr. Watson HST

Mr. Watson HST

Uses for Plastic ContainersUses for Plastic Containers

Soft-drink bottles, most commonly recycled plastic

Milk, juice and water jugs. Recycled HDPE used as trash containers, drainage pipes, garbage bags, and fencing. Second most commonly recycled plastic.

Mr. Watson HST

Uses for Plastic ContainersUses for Plastic Containers

vinyl siding, magnetic stripe cards, window profiles, gramophone records (which is the source of the term vinyl records), insultation on electrical wire, pipe, plumbing and conduit fixtures.

various containers, dispensing bottles, wash bottles, tubing, plastic bags for computer components, and various molded laboratory equipment. Its most common use is in plastic bags

Mr. Watson HST

Plastic ContainersPlastic Containers

food packaging, ropes, textiles, stationery, plastic parts and reusable containers of various types, laboratory equipment, loudspeakers, automotive components, and polymer banknotes

plastic model assembly kits, license plate frames, plastic cutlery,CD "jewel" cases

Mr. Watson HST

Plastic ContainersPlastic Containers

Container manufactured using a blend of plastics, eg two or moreplastics (PET and any other polymer), the container should beidentified 7.

Mr. Watson HST

Polyethylene terephthalatePolyethylene terephthalate (aka (aka PETPET) )

+

Mr. Watson HST

PolyethylenePolyethylene

Mr. Watson HST

PolyethylenePolyethylene

Mr. Watson HST

Polyvinyl ChloridePolyvinyl Chloride

Mr. Watson HST

PolypropylenePolypropylene

Mr. Watson HST

PolystyrenePolystyrene

Mr. Watson HST

Benzene-AromaticityBenzene-Aromaticity

Mr. Watson HST

TolueneToluene

Mr. Watson HST

2,4,6-Trinitrotoluene2,4,6-Trinitrotoluene

NO2

NO2

O2NHNO3

H2SO4

Mr. Watson HST

Mr. Watson HST

Alcohols and Carboxylic AcidsAlcohols and Carboxylic Acids

Alcohol R’-O-H

O

Carboxylic acid R-C-O-H

O

Ester R-C-O- R’

where R & R’=> alkyl group => CH3-(CH2)n-

n = 0, 1, 2, 3, etc

==

Mr. Watson HST

Triglycerides – Fats and Oils Triglycerides – Fats and Oils SoapSoap

O

CH2-O-C-R

O

CH -O-C-R’

O

CH2-O-C-R”

==

=

OCH2-O-H Na-O-C-R

OCH -O-H Na-O-C-R’

OCH2-O-H Na-O-C-R”

==

=

NaOH

heat

fat or oil glycerol fatty acid salts

Mr. Watson HST

Triglycerides – Fats and Oils Triglycerides – Fats and Oils BiodieselBiodiesel

O

CH2-O-C-R

O

CH -O-C-R’

O

CH2-O-C-R”

==

=CH2-O-H CH -O-HCH2-O-H3 CH3OH

heat

fat or oil

glycerol

methyl estersbiodiesel

OCH3-O-C-R =

OCH3-O-C-R’=

OCH3-O-C-R”=

+

+

+

Mr. Watson HST

Triglycerides – Fats, SaturatedTriglycerides – Fats, Saturated

O

CH2-O-C-C7H15

O

CH -O-C-C7H15

O

CH2-O-C-C7H15=

==

saturated – fat - solid

Mr. Watson HST

Triglycerides – Oils, UnsaturatedTriglycerides – Oils, Unsaturated O

CH2-O-C-(CH2)nCH=CH(CH2)nCH3

OCH -O-C- (CH2)nCH=CH(CH2)nCH3

OCH2-O-C- (CH2)nCH=CH(CH2)nCH3

==

=

unsaturated – oil - liquid

Mr. Watson HST

NitroglycerinNitroglycerin

CH2-O-HCH -O-HCH2-O-H-

- HNO3

CH2-NO2

CH –NO2

CH2-NO2--

Mr. Watson HST

CholesterolCholesterol

Mr. Watson HST

AlcoholsAlcohols

Methanol – CH3OH

Ethanol – CH3CH2OH

Mr. Watson HST

EthanolEthanol

CH3CH2OH CH2=CH2 + H2

ethanol catalyst ethylene

Important in 1970-1990s for plastic production

Mr. Watson HST

SugarsSugars

Mr. Watson HST

EthanolEthanol

C6H12O6 3 CH3CH2OH

glucose enzyme ethanol

unbalanced

Mr. Watson HST

StarchStarch(C6H12O6)n 3n CH3CH2OH

starch enzyme ethanol

corn

unbalancedImportant in 21st century as source of fuel

Mr. Watson HST

Synthetic RubberSynthetic Rubber

1,3-Butadiene

= =n ( )n=

butadiene rubber

Mr. Watson HST

Synthetic RubberSynthetic Rubber

vulcanization

Mr. Watson HST

Neoprene RubberNeoprene Rubber

SCl2

n

= =

= =

sss

s

sss

s

Cl

Cl

Cl

Cl

Cl

Cl

ss

s

s

Cl

Cl