Organic Chemistry

THE NATURE OF ORGANIC CHEMISTRY

ORGANIC CHEMISTRY

is the study of the properties of the compounds of carbon that are organic. All carbon compounds except for a few inorganic carbon compounds are

The name organic chemistry came from the word ORGANISM. Prior to 1828, all organic compounds had been obtained from organisms or their remains.

JNS JACOB BERZELIUS

A physician by trade, first coined the term ORGANIC CHEMISTRY in 1807 for the study of compounds derived from biological sources.

Up through the early 19th century, naturalists and scientists observed critical differences between compounds that were derived from living things and those that were not.

The belief then was that the synthesis of organic compounds from inorganic compounds in the laboratory was impossible.

Inorganic carbon compounds include the oxides of carbon, the bicarbonates and carbonates of metal ions, the metal cyanides, and a few others.

There are over six million organic compounds characterized, including the foods we eat, (made of carbohydrates, lipids, proteins and vitamins), furs & feathers, hides & skins & the organisms they came from.

Not to mention plastics, synthetic and natural fibers, dyes and drugs, insecticides and herbicides, ingredients in perfumes and flavoring agents, and petroleum products.

Chemists during those period noted that there seemed to be an essential yet inexplicable difference between the properties of the two different types of compounds.

The vital force theory (sometimes called "vitalism") was therefore proposed (and widely accepted) as a way to explain these differences.

VITALISM proposed that there was something called a "vital force" which existed within organic material but did not exist in any inorganic materials.

All efforts had failed and scientists became convinced that some "vital force" that living organisms had was necessary to make an organic compound.

As an example is the synthesis of UREA from inorganic substances in 1828 led to the disappearance of this vital force theory.

Organic chemistry defines life. Just as there are millions of different types of livingorganismson this planet, there are millions of different organicmolecules, each with different chemical and physical properties.

There are organic chemicals that make up your hair, your skin, your fingernails, and so on. The diversity of organic chemicals is due to the versatility of the carbonatom.

WHY IS CARBON SUCH A SPECIAL ELEMENT?

Carbon (C) appears in the second row of the periodic table and has 4 bonding electronsin itsvalenceshell.

Carbon therefore forms four bonds with otheratoms(each bond consisting of one of carbon's electrons and one of the bonding atom's electrons).

Carbon forms 4 bonds

Everyvalence electronparticipa tes in bonding, thus a carbon atom's bonds will be distributed evenly over the atom's surface. These bonds form a tetrahedron (a pyramid with a spike at the top), as illustrated:

The

simplest

organic

chemicals, only

calledhydrocarbons, The (called simplest METHANE)

contain

carbon and hydrogen atoms. hydrocarbon contains a

single carbon atom bonded to four hydrogen atoms: METHANE a carbonatom

bonded to 4 hydrogen atoms

But

carbon

can as

bond

to

other to in

carbonatomsin hydrogen,

addition illustrated

themoleculeETHANE:

ETHANE - a carbon-carbon bond

In fact, the uniqueness of carbon comes from the fact that it can bond to itself in many different ways. Carbonatomscan form long chains:

HEXANE - a 6-carbon chain

branched chains:

ISOHEXANE - a branchedcarbon chain

rings:

CYCLOHEXANE - a ringed hydrocarbon There appears to be almost no limit to the number of different structures that carbon can form.

To add to the complexity of organic chemistry, neighboring carbonatomscan form double and triple bonds in addition to single carbon-carbon bond.

Keep in mind that each carbonatomforms FOUR BONDS. As the number of bonds between any two carbon atoms molecule : , the number of hydrogen atoms in the

Single bonding

Double bonding

Triple bonding

Why is Organic Chemistry IMPORTANT?

It is important because it is the study of

LIFE

and

all

of

the

chemical reactions related to life.

Several careers apply an understanding of organic chemistry, such as doctors, veterinarians, dentists, pharmacologists, chemical engineers, and chemists.

Organic chemistry plays a part in the development of common household chemicals, foods, plastics, drugs, fuels... really most of the chemicals part of daily life.

CLASSIFICATION OF ORGANIC COMPOUNDS

1)FUNCTIONAL GROUPS

HYDROCARBONS contain only C &

H. In addition to carbon and hydrogen,hydrocarbonscan also contain other elements. Hydrogens in hydrocarbons can be replaced by other atoms or groups of atoms.

These replacements, called functional groups are the reactive sites in molecules. In fact, many common groups ofatomscan occur within organic molecules, these groups of atoms are called functional groups. One good example is thehydroxyl

functional group.

GROUP
The atom group HYDROXYL of a single to a (-OH). bound of GROUP oxygen single The that consists hydrogen

atom

hydrocarbons

contain a hydroxyl functional group is called alcohols. The alcohols are named a in a is that similar fashion to the simple hydrocarbons, this case prefix attached to a root ending (in "anol") designates the alcohol.

hydroxyl functional group

The contains family a of carboxylic (-COOH) acids carboxyl functional

group. Acetic acid is an example.

ETHANOL, common drinkingalcohol, is the active ingredient in "alcoholic" beverages such as beer and wine.

The concept of functional groups is central in organic chemistry, both as a means to classify structures and for predicting properties. A functional group is a molecular module, and the reactivity of that functional group is assumed, within limits, to be the same in a variety of molecules.

Functional groups can have decisive influence on the chemical and physical properties of organic compounds. Molecules are classified on the basis of their functional groups.

Alcohols, for example, all have the subunit C-O-H. All alcohols tend to be somewhat hydrophilic, usually form esters, and usually can be converted to the corresponding halides. Most functional groups feature hetero atoms (atoms other than C and H).

The atom that is not carbon is called theheteroatom. The heteroatom's bonds must be shown or clearly understood. For example, nitrogen normally forms three bonds, so three bonds must be indicated for it. Oxygen normally forms two, so two bonds must be shown. Rings may have more than one heteroatom.

In organic chemistry, there are a few basic structural shapes that you will encounter. They are chains and rings . There are also two types of chains, a straight chain , and a branched chain . In a straight chain, one carbon atom holds no more than two other carbon atoms. As its name implies, the straight chain is a straight link of carbon, sometimes oxygen or nitrogen, atoms, in structural formula that is. Because of twisting and

Branched chains have at least one carbon holding more than two other carbon atoms. It will, as its name implies, have branches of other chains coming off another chain. have at least one carbon holding more than two other carbon atoms. It will, as its
H H H H H H H name implies, have branches of other chains coming | | | | | | | H-C-C-C-C-C-C-H off another chain. Branching H one H-C-H H H H is H H of the reasons | | | | | | | | | | | | | H H there H---C---C-C---C---C-C-C-H why H H H H are so many isomers for each compound. | | | | | | | Straight Chain H-C-H H H H H H H | H-C-H | H Branched Chain

Rings (or cyclic compounds) are composed of rings of carbon and sometimes oxygen or nitrogen. For example, cyclohexane has a ring of six carbon atoms.

A cyclohexane molecule inCHAIRCONFORMATION. Hydrogen atoms in axial positions are shown in red, while those

ETHYNE ACETYLENE

ISOBUTANE

The hydroxyl group consists of a single oxygen atom bound to a single hydrogen atom (-OH). The group of hydrocarbons that contain a hydroxyl functional group is calledalcohols.

The alcohols are named in a similar fashion to the simple hydrocarbons; a prefix is attached to a root ending (in this case "anol") that designates the alcohol.

The existence of the functional group completely changes the chemical properties of the molecule. Ethane, the two-carbon alkane, is a gas at room temperature; ethanol, the two-carbon alcohol, is a liquid. Double & triple bonds are considered to be functional groups.

Some common functional groups are: ALKANE, ALKENE, ALKYNE, ALCOHOL, KETONE, ALDEHYDE, CARBOXYLIC ACID, ESTER, AMIDE & NITRILE. The "R" group is a generic group, and is not a part of the functional group of interest.

Compounds with the same functional group form a homologous series having similar chemical properties and often exhibiting a regular gradation in physical properties with increasing molecular weight.

2) Aliphatic compounds

The aliphatic hydrocarbons are subdivided into three groups of HOMOLOGOUS SERIESaccording to their state ofSATURATION:

>Wherenrepresents the number of carbon atoms present.

>HOMOLOGOU GENERAL S SERIES FORMULA Straight Chain C n H 2 n +2 ( n 1) Alkanes Alkyl C n H 2 n +1 ( n 1) Alkenesand C n H 2 n ( n 2) CyclicAlkanes Alkynes C n H 2 n 2 (n 2) Alcohols C n H (2n+1) OH

EXAMPLE CH 4 , n = 1 CH 3 , n = 1 C 2 H 4 , n = 2 C 2 H 2 , n = 2 CH 3 OH, n =1

FUNCTIONAL GROUP

C=C CC -OH

( n 1)

Carboxylic acids ( n 0) C n (H 2 O) n ( n 1) C n H 2 n +1 COOH

CH 2 O 2 , n = 0

- COOH

Carbohydrates

C 6 H 12 O 6

Compounds are:
paraffins, which are alkanes WITHOUT any double or triple bonds, olefins or alkenes WHICH CONTAINS one or more double bonds, i.e di-olefins (dienes) or poly-olefins. alkynes, WHICH HAS one or more

The rest of the group is classed according to the functional groups present. Such compounds can be "straight-chain," branched-chain or cyclic.

Both saturated (alicyclic compounds) and unsaturated compounds exist as cyclic derivatives. The most stable rings contain five or six carbon atoms, but large rings (macrocycles) and smaller rings are common.

The smallest cycloalkane family is the three-memberedcyclopropane (CH 2 ) 3 Saturated cyclic compounds contain single bonds only, whereas aromatic rings have an alternating (or conjugated) double bond.

To illustrate the rules, here are some types of cyclic compounds:

cyclopropan e

cyclobutan e

cyclopenta ne

cyclohexan e

cyclohexene

Bromocyclohexan e

IUPAC NAME

Cycloalkanesdo not contain multiple bonds, whereas the cycloalkenesand the cycloalkynes do.

) Aromatic Compound

Aromatichydrocarbons contain conjugateddouble bonds. The most important example isbenzene, the structure of which was formulated by Kekul who first proposed the delocalizationorresonance principle for explaining its structure.

Benzene > is one of the best-known aromatic compounds as it is one of the simplest and most stable aromatics.

4) Heterocyclic compounds

The ring is termed aheterocycle. Pyridineandfuranare examples of aromatic heterocycles whilepiperidine andtetrahydrofuran are the corresponding alicyclic heterocycles.

The heteroatom of heterocyclic molecules is generally oxygen, sulfur, or nitrogen, with the latter being particularly common in biochemical systems.

Examples of groups among the heterocyclic are the aniline dyes, the great majority of the compounds discussed in biochemistry such as alkaloids, many compounds related to vitamins, steroids, nucleic acids (e.g. DNA, RNA) and also numerous medicines.

Heterocyclic with relatively simple structures are pyrrole (5membered) and indole (6membered carbon ring). Rings can fuse with other rings on an edge to givepolycyclic compounds. Thepurinenucleoside bases are notable polycyclic aromatic

Rings can also fuse on a "corner" such that one atom (almost always carbon) has two bonds going to one ring and two to another. Such compounds are termedspiroand are important in a number of natural products.

Pyridine
A simple heterocyclic compound

Furan
A 5 ring heteroatom

Tetrahydrofuran
IUPAC NAME: OXACYCLOPENTANE

5) Polymers

One important property of carbon is that it readily forms chain or even networks linked by carbon-carbon bonds. The linking process is called POLYMERIZATION, of the chains or networks polymers, while the source compound is aMONOMER. An example of a polymer that is made up or of a polystyrene is a swimming board.

Two main groups of polymers exist: those artificially manufactured are referred to as industrial polymersor synthetic polymers and those naturally occurring asbiopolymers. Since the invention of the first artificial polymer,bakelite, the family has quickly grown with the

Common synthetic organic polymers arepolyethylene (polythene), polypropylene,nylon,teflon, polystyrene,polyesters, polymethyl methacrylate(called perspex and

Natural polymers (from the Greek poly meaning many and meros meaning parts) are found in many forms such as horns of animals, tortoise shell, shellac (from the lac beetle), rosin (from pine trees), asphalt, and tar from distillation of organic materials.

One of the most useful of the natural polymers was rubber, obtained from the sap of the hevea tree. (Rubber was named by the chemist Joseph Priestley who found that a piece of solidified latex gum was good for rubbing out pencil marks on paper.

In Great Britain, erasers are still called rubbers.) Natural rubber had only limited use as it became brittle in the cold and melted when warmed.

In 1839, Charles Goodyear discovered, through a lucky accident, that by heating the latex with sulfur, the properties were changed making the rubber more flexible and temperature stable. That process became known as vulcanization.

The first synthetic polymer, a phenol-formaldehyde polymer, was introduced under the name Bakelite, by Leo Baekeland in 1909. Its original use was to make billiard balls. Rayon, the first synthetic fiber was developed as a replacement for silk in 1911.

CH 3 CH 2 =C-CH=CH 2
2-methyl-1, 3-butadiene
Natural rubber is a polymer of isoprene

Since latex will solidify in air, a stabilizer is added to prevent polymerization if the latex is to be stored or shipped in liquid form.

>The repeating unit of the polymer

Polypropylene

6) Biomolecules

Maitotoxin
a complex organic biological toxin

BIOMOLECULAR CHEMISTRYis a major category within organic chemistry which is frequently studied by biochemists. Many complex multifunctional group molecules are important in living organisms.

Some are long-chainbiopolymers, and these includepeptides,DNA,RNAand thepolysaccharidessuch asstarches in animals andcellulosesin plants.

The other main classes are amino acids(monomer building blocks of peptides and proteins), carbohydrates(which includes the polysaccharides), the nucleic acids(which include DNA and RNA as polymers), and the

In addition, animal biochemistry contains many small molecule intermediates which assist in energy production through theKrebs cycle, and producesisoprene, the most common hydrocarbon in animals.

Isoprenes in animals form the importantsteroidstructural ( cholesterol) and steroid hormone compounds; and in plants form terpenes,terpenoids, some alkaloids, and a unique set of hydrocarbons called biopolymer polyisoprenoids present inlatex

7) Peptide Synthesis 8) Oligonucleotide Synthesis 9) Carbohydrate Synthesis

Comparison between Organic and Inorganic

ORGANIC COMPOUNDS

INORGANIC COMPOUNDS

*Organic compounds *Inorganic compounds do contain carbon. *Organic not contain carbon. Compounds are Inorganic Compounds are composed of few elements composed of all the known only.C, H,O,N,S,P and elements. halogens are the most common. *Organic compounds contain carbon-hydrogen * Inorganic compounds do not have carbon-

ORGANIC COMPOUNDS

INORGANIC COMPOUNDS

*They are generally found *They are generally in living matter, i.e., obtained from non-living animals and plants & matter, i.e., minerals. therefore produced by Produced by non-living living things. natural processes or by human intervention in the laboratory. *Chemical reactions *Chemical reactions are molecular and are ionic and fast. slow. The yields are The yields are poor due to side quantitative and reactions. there is no side

*They are usually gases, liquids or solids having low melting points.

ORGANIC COMPOUNDS

*They are usually solids having high melting and boiling points.

INORGANIC COMPOUNDS

*Organic compds *Inorganic cannot form salts. compounds can These, being form salts. These, covalent being electrovalent compounds, are compounds, are generally insoluble generally soluble in in water and other water and other polar solvents. polar solvents.

*The co-ordination compounds show the phenomenon of isomerism only. *They have been classified *Homologous series are into many classes on the not found. The basis of functional groups. compounds are mainly Each class is represented divided as acids, bases by a general formula and and salts. the members show similar properties. Each class is known as homologous series.

*They exhibit the phenomenon of isomerism.

ORGANIC COMPOUNDS

INORGANIC COMPOUNDS

*Some compounds *Inorganic are highly complex compounds are less and have high complex. molecular masses. Comparatively a These complex complex compound compounds are is generally less stable. stable. * Inorganic compounds * Organic compounds contain metal atoms. does not contain metal atoms.

ORGANIC COMPOUNDS

INORGANIC COMPOUNDS

In general, if a compound contains carbon it is organic. The reason for this is that carbon is considered to be the building block of life, and inorganic compounds are said to be more mineral than biological.

There are, however, a few cases of carbon-containing compounds which are considered inorganic because of convention, some being carbonates, simple oxides of carbon, cyanides and the allotropes of carbon.

ISOMERISM- is the phenomenon whereby certain compounds, with the same molecular formula, exist in different forms owing to their different organizations of atoms.

The concept of isomerism illustrates the fundamental importance of molecular structure and shape in organic chemistry. Isomers are molecules that have the same chemical formula but different structural formulas.

CH 3 I CH 3 CH 2 CH CH 2 CH 3

CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 or C6H14 or hexane