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Organic Chemistry. The Chemistry of Carbon Compounds. Carbon. “Organic” Chemistry. Historically, organic compounds are defined as compounds extracted or isolated from plants and animals. - PowerPoint PPT Presentation
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Organic ChemistryThe Chemistry of
Carbon Compounds
CarbonCarbon
““Organic” ChemistryOrganic” Chemistry• Historically, organic compounds are
defined as compounds extracted or isolated from plants and animals.– VITALISM: Scientists believed that
organic compounds contained a vital force that was only found in living systems
• Disproved by Friederich Wohler in 1828 by synthesizing urea using inorganic materials (silver cyanate and ammonium chloride)
AgOCN + NH4Cl CNH2 NH2
O
Friederich WohlerFriederich Wohler
Organic ChemistryOrganic Chemistry• Study of carbon compounds
– Composed of carbon, hydrogen, oxygen, nitrogen, sulfur, phosphorus, and the halogens
• More than 95% of known compounds are organic compounds (Carbon-containing)
• Recall– Carbons can have 4 bonds– Nitrogen can have 3 bonds– Oxygen can have 2 bonds– Hydrogen can have 1 bond
Common Elements in Organic Compounds
C, H, O, (N, S)
The Secret to Organic The Secret to Organic Compounds: the unique Compounds: the unique
carbon atomcarbon atom• CATENATION
– Ability of C-atoms to bond to each other so strongly, they can form long chains. Eg. Thousands of C-atoms bonded.
– Each carbon can have four bonds, maximum
Common organic compound Common organic compound families families
• HYDROCARBONS: Only C and H– Alkanes, alkenes, alkynes, arenes,
aromatic compounds• OXYGEN-CONTAINING
– Alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, acid anhydrides
• NITROGEN-CONTAINING– Amines, Amides
ExamplesExamples
C
CH
CH
CH
CH
CH
CH
O
C
CH
C
CH
CH
CH
OH
CO
O
CH3 CH
O
C
C
C
OH OH
OCH
CH2
OH
OH
benzaldehyde m ethyl salicylate ascorbic acid
C
CH3
CH3
O C
CH3
OH
OCH3
CH2CH3
Cl C Cl
F
Facetone acetic acid propane Freon 12
Classification of Hydrocarbons
HydrocarbonsHydrocarbons
Hydrocarbons: AlkanesHydrocarbons: Alkanes
• Simplest hydrocarbons• Contains only C–C and C–H bonds • Usually used as fuels• Three types
– Straight chain alkanes– Branched alkanes– Cyclic alkanes
Examples of AlkanesExamples of Alkanes
Structures of AlkanesStructures of Alkanes
C H
H
H
H
= CH4
C C
H
H
H
C
H
H
H
H
H
=
C C
H
H
H
C
H
H
C
H
H
H
H
H
=
CH3CH2CH3
CH3CH2CH2CH3
C C
H
H
H
C
H
CH3
H
H
H
CH3 CH CH3
CH3
=
m ethane
propane
butane
isobutane
Structural IsomersStructural Isomers
Structural IsomersStructural Isomers
CycloalkanesCycloalkanes
• Alkanes that form rings are called cycloalkanes
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2CH2
CH2
CH2
CH2
CH2
=
=
=
=
cyclopropane
cyclobutane
cyclopentane
cyclohexane
HaloalkanesHaloalkanes
• Alkanes with halogens
Cl C Cl
F
F
Cl C Cl
Cl
F
F C C
Cl
F F
F
Cl
Freon 11Freon 11 Freon 12Freon 12 Freon 14Freon 14
ChlorofluorocarbonsChlorofluorocarbons
• Insoluble in water and are unreactive towards substances
• Unreactiveness lets them reach the stratosphere and react with the ozone layer
AlkenesAlkenes
AlkynesAlkynes
• Contains a C≡C bonds
August Kekule and the August Kekule and the DreamDream
• C6H6
• "...I was sitting writing on my textbook, but the work did not progress; my thoughts were elsewhere. I turned my chair to the fire and dozed. Again the atoms were gamboling before my eyes. This time the smaller groups kept modestly in the background. My mental eye, rendered more acute by the repeated visions of the kind, could now distinguish larger structures of manifold conformation; long rows sometimes more closely fitted together all twining and twisting in snake-like motion. But look! What was that? One of the snakes had seized hold of its own tail, and the form whirled mockingly before my eyes. As if by a flash of lightning I awoke; and this time also I spent the rest of the night in working out the consequences of the hypothesis."
• "I fell into a reverie, and lo, the atoms were gamboling before my eyes! Whenever, hitherto, these diminutive beings had appeared to me, they had always been in motion; but up to that time, I had never been able to discern the nature of their motion. Now, however, I saw how, frequently, two smaller atoms united to form a pair; how a larger one embraced the two smaller ones; how still larger ones kept hold of three or even four of the smaller; whilst the whole kept whirling in a giddy dance. I saw how the larger ones formed a chain, dragging the smaller ones after them, but only at the ends of the chain. . . The cry of the conductor: “Clapham Road,” awakened me from my dreaming; but I spent part of the night in putting on paper at least sketches of these dream forms. This was the origin of the Structural Theory."
24.3
Aromatic Hydrocarbons
C
CC
CC
C
H
H
H
H
H
H
C
CC
CC
C
H
H
H
H
H
H
Aromatic HydrocarbonsAromatic Hydrocarbons• Cyclic structures with alternating C–C
and C=C bonds
24.3
Polycyclic Aromatic Hydrocarbons
Functional GroupsFunctional Groups
• Determines the properties of the organic compound– Compounds with the same
functional group will react similarly• Alkenes: –C=C– bond• Alkynes: –C≡C– bond• Aromatic hydrocarbons: cyclic
structure with alternating –C–C– and –C=C– bonds
AlcoholsAlcohols
• has the general structure R–OH– derived from hydrocarbons and
contain -OH groups• Polar molecules and are soluble
in water (Why?)
Some Common AlcoholsSome Common Alcohols
• CH3OH (methanol)
– Used as an industrial solvent– Possible replacement for gasoline in
automobiles
• CH3CH2OH (ethanol)
– Made from fermentation of grain or other sugar materials
– Made by reaction of ethylene with water (denatured alcohol)
– Used for beverages and fuels
Some Common AlcoholsSome Common Alcohols• Isopropyl Alcohol
– Also known as rubbing alcohol– Used as a disinfectant
• Ethylene glycol– Also known as antifreeze– Has multiple –OH groups
CH3
CHCH3
OH
C C
H
OH
H H
OH
H
AlcoholsAlcohols
Sterols, ethylene glycol
C6H12O6 (aq) 2CH3CH2OH (aq) + 2CO2 (g)enzyme
CH2 CH2 (g) + H2O (g) CH3CH2OH (g)H2SO4
Biological production of ethanol
Commercial production of ethanol
Metabolic oxidation of ethanol
CH3CH2OH CH3CHO + H2
alcohol dehydrogenase
DRINKABLE vs. DENATURED Alcohol
EthersEthers
• Has the R-O-R’ general structure• Compounds in which two
hydrocarbons linked by an oxygen are called ethers.
• Used as general anesthetic• Used as solvents• Less soluble in water than
alcohols
EthersEthers
CH3
OCH2
CH2CH3
CH C O
CH3F
F
Cl
Cl
methyl propyl ether methoxy flurane
CH3 O C CH3
CH3
CH3
methyl tert-butyl ether
Compounds with a Carbonyl Compounds with a Carbonyl GroupGroup
• Carbonyl functional group is C=O• Types of different carbonyl
compounds– Aldehydes– Ketones– Carboxylic Acids– Esters– Amides
Aldehydes and KetonesAldehydes and Ketones• Aldehydes must have at least one H
atom attached to the carbonyl group:
• Ketones must have two C atoms attached to the carbonyl group:
RCH
O
RCR'
O
Functional Group Chemistry
H C H
O
H C
O
CH3 C
O
CH3H3C
formaldehyde acetaldehyde acetone
ALMONDS, FORMALIN
Carboxylic AcidsCarboxylic Acids
• Carboxylic acids contain a carbonyl group with an -OH attached.
• The carboxyl functional group is -COOH
• Carboxylic acids are weak acids.
RCOH
O
VINEGAR, ASPIRIN, FACIAL WASH, ANTS, CITRUS FRUITS, PROTEINS, PRESERVATIVES
Common Carboxylic Common Carboxylic AcidsAcids
EstersEsters
• Esters contain -COOR groups:
• Usually have fruity odors and tastes
R'COR
O
Ester Flavors and Ester Flavors and FragrancesFragrances
CH3
CH2CH2
CO
O
CH3
CH3
CH2CH2
CO
O
CH2
CH3
CH3
CO
O
CH2
CH2
CH2CH2
CH3
CH3
CO
O
C
CH
C
CH
CH
CH
OH
CO
O
CH3
m ethyl salicylate(w intergreen)
m ethyl butyrate (apple)
ethyl butyrate(pineapple)
pentyl acetate (banana)
benzyl acetate(jasm ine)
Functional Group Chemistry
Esters have the general formula R’COOR, where R is a hydrocarbon group.
CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2O
O
ethyl acetate
Banana: isopentyl acetatePineapple: ethyl butanoateApple: methyl butanoatePear: propyl ethanoateOrange: Octyl ethanoateRaspberry: 2-Methylpropyl ethanoateOil of Wintergreen: methyl salycilate
Esters Galore!Esters Galore!
allyl caproate pineapple amyl acetate apple, banana amyl butyrate apricot, pear,
pineapple amyl caproate apple, pineapple amyl valerate apple benzyl acetate pear, strawberry bornyl acetate pine tree flavor
iso-butyl acetate cherry, raspberry, strawberry
ethyl acetate peach, pineapple, raspberry ethyl butyrate banana, pineapple, strawberry ethyl caproate strawberry ethyl cinnamate cinnamon ethyl formate lemon, strawberry ethyl heptoate grape, pineapple ethyl isovalerate apple ethyl heptanoate apricot, cherry, grape, raspberry ethyl lactate grape
ethyl pelargonate grape geranyl acetate geranium geranyl butyrate cherry geranyl valerate apple linalyl acetate lavender,sage linalyl butyrate peach linalyl formate apple, peach menthyl acetate peppermint methyl benzyl acetate cherry methyl cinnamate strawberry methyl phenyl acetate honey methyl salicylate wintergreen methyl anthranilate grape,jasmine nonyl caprylate orange octyl butyrate parsnip terpenyl butyrate cherry
HOW TO MIMIC NATURE: HOW TO MIMIC NATURE: Making synthetic Making synthetic
flavoringflavoring• A good cherry is supposed to be tough to
formulate. Here is an example of a *minimum* synthetic cherry flavoring:
• ethyl methyl p-tolyl glycidate 16.0 % iso-amyl acetate 12.0 %
iso-butyl acetate 12.0 % p-methyl benzyl acetate 11.0 % benzaldehyde 8.0 % vanillin 7.0 % benzyl alkcohol 5.5 % piperonal 5.0 % ethyl caprate 4.0 % cinnamic aldehyde dimethyl acetal 3.0 % p-tolyl aldehyde 3.0 % cinnamyl anthranilate 3.0 % ethyl caproate 2.0 % geranyl butyrate 2.0 % terpenyl butyrate 0.5 %
AminesAmines
• Organic bases• Contain carbon, hydrogen, and nitrogen
CH2
CH2CH2
CH2
CH2
NH2NH2
CH2
CH2CH2
CH2
NH2
NH2
cadaverine putresine
CH2
CH
CH2
NH
CH2
CH2
CH2
CH2
CH3
coniine
C
CH
CH
CH
CH
CH
CH2
CH
NH
CH3
CH3
m etham phetam ine
AmidesAmides• composites of carbonyl and amine functionalities• proteins
RCN
O
R'
H
Name the functional Name the functional groupgroup
C
CH
CH
CH
CH
CH
CH
O
C
CH
C
CH
CH
CH
OH
CO
O
CH3 CH
O
C
C
C
OH OH
OCH
CH2
OH
OH
benzaldehyde m ethyl salicylate ascorbic acid
C
CH3
CH3
O C
CH3
OH
OCH3
CH2CH3
Cl C Cl
F
Facetone acetic acid propane Freon 12
Compounds with multiple Compounds with multiple functional groupsfunctional groups
CCCH
CCH2
O
ONHCH2
OH
OH
CH2
CH3
CH3
OH CCCH
CCH2
O
ONHCH2
OH
OH
CH2
CH3
CH3
OH CCCH
CCH2
O
ONHCH2
OH
OH
CH2
CH3
CH3
OH CCCH
CCH2
O
ONHCH2
OH
OH
CH2
CH3
CH3
OH
Vitamin B5
Pantothenic acid
MangMangoo
Would you eat this?Would you eat this?-Terpinolene, Ethyl butanoate, 3-Carene, Ethyl
acetate, Ethyl 2-butenoate, -Terpinene, -Thujene, Dimethyl sulfide, Limonene, -Phellandrene, Myrcene, p-Cymen-8-ol, -Caryophyllene, cis-3-Hexene-1-ol, hexadecyl acetate, 5-Butyldihydro-3H-2-furanone, trans-2-hexenal, Ethyl tetradeconaoate, -Humulene, sabinene, 2-Carene, Camphene, Ethyl octanoate, 4-Isopropenyl-1-methylbenzene 1-Hexanol, -terpinene, hexanal, Ethyl hexadecanoate, -Copaene, Hexadecanal, Ethanol, Ethyl propionate, Dihydro-5-hexyl-3H-2-furanone, Carveol, Geranial, Ethyl decanoate, Furfural, Butyl acetate, Methyl butanoate, 2,3, Pentanedione, 1,1, diethoxyethane, pentadecanal, Butyl formate, 1-Butanol, 5-Methylfurfural, Ethyl dodecanoate, 2-Acetylfuran, 2 Methyl-1-butanol, 4-Methylacetophenoen, Acetaldehyde, Cyclohexane
FOSSIL FUELSFOSSIL FUELS
• Coal, Petroleum, Natural Gas• From decayed organic matter• Makes up 90% of energy used
CoalCoal
• Main element is carbon, but contains small% of other elements
• Complete combustion:
– C(s) + O2(g) CO2(g)
• Limited supply, strip mining
Natural GasNatural Gas
• Principally methane• Formed ages ago probably by heat,
pressure, and action of bacteria on organic matter.
Chemistry In Action: The Petroleum Industry
Crude Oil
The Guimaras Oil SpillThe Guimaras Oil Spill
Gasoline: C5-C12 alkanesGasoline: C5-C12 alkanes• C5-C12 alkanes, some sulfur and nitrogen-containing
hydrocarbons• >C15, difficult to combust, causes knock• OCTANE Rating: Isooctane (CH3)3CCH2CH(CH3)2 = 100
Heptane = 0• Some cpds improving octane rating: tetraethyllead
DieselDiesel• Runs on engine designed by Engineer Rudolf Diesel• Petrodiesel: It is a hydrocarbon mixture, (C10-C15) obtained
in the fractional distillation of crude oil between 250 °C and 350 °C.
• Biodiesel: Methyl esters of fats from natural oils
POLYMERSPOLYMERS• Poly: Many Meros: Parts• Made up of repeating monomers
• Copolymer is a polymer made up of two or more monomers
• Common biopolymers: Proteins, DNA, RNA, starch, cellulose
( CH CH2 CH2 CH CH CH2 )n
Some commercial Some commercial polymerspolymers
• PET: Polyethylene terephthalate– Plastic bottles
• Polytetrafluoroethylene– Teflon™
• Polypropylene• Polystyrene• Polyvinyl chloride• Nylon (synthetic
polyamide, similar to bonds in proteins)
http://www.nationalgeographic.com/education/plastics/index.html
References:References: Hill, JW and Kolb DK. Chemistry for the Changing
Times, 7th ed. Prentice Hall International. 1992. Brown, TL. Le May, Jr., HE, and Bursten, BE.
Chemistry: The Central Science. 1997. Schmid, G. Organic Chemistry. Mosby-Year Book,
Inc. 1996. http://chemed.chem.purdue.edu/genchem/ (accessed
on July 28, 2003) Partial list of ingredients for the mango from
Snyder, C.H. “The Extraordinary Chemistry of Ordinary Things”, J. Wiley & Sons, 1998. p. 54
Picture of Mango from http://www.globalgourmet.com/ggt/ggt0598/art/mango.jpg (accessed on June 6, 2003)