Organic chemistry
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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.

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Organic Chemistry

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Organic chemistry

Organic Chemistry

The Chemistry of Carbon Compounds


Carbon

Carbon


Organic chemistry1

“Organic” 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)


Organic chemistry

Friederich Wohler


Organic chemistry2

Organic 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


Organic chemistry

Common Elements in Organic Compounds

C, H, O, (N, S)


The secret to organic compounds the unique carbon atom

The Secret to Organic Compounds: the unique carbon 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 families

Common organic compound 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


Examples

Examples


Organic chemistry

Classification of Hydrocarbons


Hydrocarbons

Hydrocarbons


Hydrocarbons alkanes

Hydrocarbons: 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 alkanes

Examples of Alkanes


Structures of alkanes

Structures of Alkanes


Structural isomers

Structural Isomers


Structural isomers1

Structural Isomers


Cycloalkanes

Cycloalkanes

  • Alkanes that form rings are called cycloalkanes


Haloalkanes

Haloalkanes

  • Alkanes with halogens

Freon 11

Freon 12

Freon 14


Chlorofluorocarbons

Chlorofluorocarbons

  • Insoluble in water and are unreactive towards substances

  • Unreactiveness lets them reach the stratosphere and react with the ozone layer


Alkenes

Alkenes


Alkynes

Alkynes

  • Contains a C≡C bonds


August kekule and the dream

August Kekule and the Dream

  • C6H6


Organic chemistry

  • "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."

  • "...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."


Organic chemistry

H

H

C

H

H

C

H

H

C

C

C

C

C

C

C

C

H

H

C

H

H

C

H

H

Aromatic Hydrocarbons

24.3


Aromatic hydrocarbons

Aromatic Hydrocarbons

  • Cyclic structures with alternating C–C and C=C bonds


Organic chemistry

Polycyclic Aromatic Hydrocarbons

24.3


Functional groups

Functional 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


Alcohols

Alcohols

  • has the general structure R–OH

    • derived from hydrocarbons and contain -OH groups

  • Polar molecules and are soluble in water (Why?)


Some common alcohols

Some 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 alcohols1

Some Common Alcohols

  • Isopropyl Alcohol

    • Also known as rubbing alcohol

    • Used as a disinfectant

  • Ethylene glycol

    • Also known as antifreeze

    • Has multiple –OH groups


Alcohols1

Alcohols

Sterols, ethylene glycol


Organic chemistry

enzyme

C6H12O6(aq) 2CH3CH2OH (aq) + 2CO2 (g)

H2SO4

CH2 CH2(g) + H2O (g) CH3CH2OH (g)

alcohol dehydrogenase

CH3CH2OH CH3CHO + H2

Biological production of ethanol

Commercial production of ethanol

Metabolic oxidation of ethanol

DRINKABLE vs. DENATURED

Alcohol


Ethers

Ethers

  • 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


Ethers1

Ethers


Compounds with a carbonyl group

Compounds with a Carbonyl Group

  • Carbonyl functional group is C=O

  • Types of different carbonyl compounds

    • Aldehydes

    • Ketones

    • Carboxylic Acids

    • Esters

    • Amides


Aldehydes and ketones

Aldehydes 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:


Organic chemistry

O

O

O

CH3

CH3

formaldehyde

acetaldehyde

acetone

H C H

H C

C

ALMONDS, FORMALIN

H3C

Functional Group Chemistry


Carboxylic acids

Carboxylic Acids

  • Carboxylic acids contain a carbonyl group with an -OH attached.

  • The carboxyl functional group is -COOH

  • Carboxylic acids are weak acids.

VINEGAR, ASPIRIN, FACIAL WASH, ANTS, CITRUS FRUITS, PROTEINS, PRESERVATIVES


Common carboxylic acids

Common Carboxylic Acids


Esters

Esters

  • Esters contain -COOR groups:

  • Usually have fruity odors and tastes


Ester flavors and fragrances

Ester Flavors and Fragrances


Organic chemistry

O

CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2O

Functional Group Chemistry

Esters have the general formula R’COOR, where R is a hydrocarbon group.

ethyl acetate

Banana: isopentyl acetate

Pineapple: ethyl butanoate

Apple: methyl butanoate

Pear: propyl ethanoate

Orange: Octyl ethanoate

Raspberry: 2-Methylpropyl ethanoate

Oil 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 making synthetic flavoring

HOW TO MIMIC NATURE: Making synthetic flavoring

  • 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 %


Amines

Amines

  • Organic bases

  • Contain carbon, hydrogen, and nitrogen


Amides

Amides

  • composites of carbonyl and amine functionalities

  • proteins


Name the functional group

Name the functional group


Compounds with multiple functional groups

Compounds with multiple functional groups


Organic chemistry

Mango


Would you eat this

Would you eat this?

a-Terpinolene, Ethyl butanoate, 3-Carene, Ethyl acetate, Ethyl 2-butenoate, a-Terpinene, a-Thujene, Dimethyl sulfide, Limonene, b-Phellandrene, Myrcene, p-Cymen-8-ol, b-Caryophyllene, cis-3-Hexene-1-ol, hexadecyl acetate, 5-Butyldihydro-3H-2-furanone, trans-2-hexenal, Ethyl tetradeconaoate, a-Humulene, sabinene, 2-Carene, Camphene, Ethyl octanoate, 4-Isopropenyl-1-methylbenzene 1-Hexanol, a-terpinene, hexanal, Ethyl hexadecanoate, a-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 fuels

FOSSIL FUELS

  • Coal, Petroleum, Natural Gas

  • From decayed organic matter

  • Makes up 90% of energy used


Organic chemistry

Coal

  • Main element is carbon, but contains small% of other elements

  • Complete combustion:

    • C(s) + O2(g)  CO2(g)

  • Limited supply, strip mining


Natural gas

Natural Gas

  • Principally methane

  • Formed ages ago probably by heat, pressure, and action of bacteria on organic matter.


Organic chemistry

Chemistry In Action: The Petroleum Industry

Crude Oil


The guimaras oil spill

The Guimaras Oil Spill


Gasoline c5 c12 alkanes

Gasoline: 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

Diesel

  • 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


Polymers

( CH CH2 CH2 CH CH CH2 )n

POLYMERS

  • 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


Some commercial polymers

Some commercial polymers


Organic chemistry

  • 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)


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