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Table of contents
- Chemistry eBooks: Organic Chemistry (Kindle Nook iPad PDF EPub Html) DigitalBookIndex
- CHM 173 - Library Resources for Organic Chemistry
- Textbooks at Carlson Library Desk (Reserve)
In this system, the endpoints and intersections of each line represent one carbon, and hydrogen atoms can either be notated explicitly or assumed to be present as implied by tetravalent carbon. By an explosion in the number of chemical compounds being discovered occurred assisted by new synthetic and analytical techniques. Grignard described the situation as "chaos le plus complet" as due to the lack of convention it was possible to have multiple names for the same compound.
This led to the creation of the Geneva rules in 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.
Chemistry eBooks: Organic Chemistry (Kindle Nook iPad PDF EPub Html) DigitalBookIndex
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 heteroatoms atoms other than C and H. Organic compounds are classified according to functional groups, alcohols, carboxylic acids, amines, etc. The aliphatic hydrocarbons are subdivided into three groups of homologous series according to their state of saturation :.
The rest of the group is classed according to the functional groups present. Such compounds can be "straight-chain", branched-chain or cyclic. The degree of branching affects characteristics, such as the octane number or cetane number in petroleum chemistry. 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-membered cyclopropane CH 2 3. Saturated cyclic compounds contain single bonds only, whereas aromatic rings have an alternating or conjugated double bond.
Cycloalkanes do not contain multiple bonds, whereas the cycloalkenes and the cycloalkynes do. Aromatic hydrocarbons contain conjugated double bonds. This means that every carbon atom in the ring is sp2 hybridized, allowing for added stability. Particular instability antiaromaticity is conferred by the presence of 4n conjugated pi electrons. The characteristics of the cyclic hydrocarbons are again altered if heteroatoms are present, which can exist as either substituents attached externally to the ring exocyclic or as a member of the ring itself endocyclic.
In the case of the latter, the ring is termed a heterocycle.
Pyridine and furan are examples of aromatic heterocycles while piperidine and tetrahydrofuran 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. Heterocycles are commonly found in a wide range of products including aniline dyes and medicines. Additionally, they are prevalent in a wide range of biochemical compounds such as alkaloids , vitamins, steroids, and nucleic acids e.
Rings can fuse with other rings on an edge to give polycyclic compounds. The purine nucleoside bases are notable polycyclic aromatic heterocycles. 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.
CHM 173 - Library Resources for Organic Chemistry
Such compounds are termed spiro and are important in a number of natural products. One important property of carbon is that it readily forms chains, or networks, that are linked by carbon-carbon carbon-to-carbon bonds. The linking process is called polymerization , while the chains, or networks, are called polymers. The source compound is called a monomer. Two main groups of polymers exist: synthetic polymers and biopolymers.
Synthetic polymers are artificially manufactured, and are commonly referred to as industrial polymers. Since the invention of the first synthetic polymer product, bakelite , synthetic polymer products have frequently been invented. Common synthetic organic polymers are polyethylene polythene , polypropylene , nylon , teflon PTFE , polystyrene , polyesters , polymethylmethacrylate called perspex and plexiglas , and polyvinylchloride PVC.
Both synthetic and natural rubber are polymers. Varieties of each synthetic polymer product may exist, for purposes of a specific use. Changing the conditions of polymerization alters the chemical composition of the product and its properties.
These alterations include the chain length , or branching , or the tacticity. With a single monomer as a start, the product is a homopolymer. Secondary component s may be added to create a heteropolymer co-polymer and the degree of clustering of the different components can also be controlled. Physical characteristics, such as hardness, density , mechanical or tensile strength , abrasion resistance, heat resistance, transparency, colour, etc. Biomolecular chemistry is a major category within organic chemistry which is frequently studied by biochemists. Many complex multi-functional group molecules are important in living organisms.
Some are long-chain biopolymers , and these include peptides , DNA , RNA and the polysaccharides such as starches in animals and celluloses in 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 lipids. In addition, animal biochemistry contains many small molecule intermediates which assist in energy production through the Krebs cycle , and produces isoprene , the most common hydrocarbon in animals.
Isoprenes in animals form the important steroid structural cholesterol and steroid hormone compounds; and in plants form terpenes , terpenoids , some alkaloids , and a class of hydrocarbons called biopolymer polyisoprenoids present in the latex of various species of plants, which is the basis for making rubber. In pharmacology, an important group of organic compounds is small molecules , also referred to as 'small organic compounds'.
Textbooks at Carlson Library Desk (Reserve)
In this context, a small molecule is a small organic compound that is biologically active, but is not a polymer. Fullerenes and carbon nanotubes , carbon compounds with spheroidal and tubular structures, have stimulated much research into the related field of materials science. The first fullerene was discovered in by Sir Harold W. Kroto of the United Kingdom and by Richard E. Smalley and Robert F. Curl, Jr. Using a laser to vaporize graphite rods in an atmosphere of helium gas, these chemists and their assistants obtained cagelike molecules composed of 60 carbon atoms C60 joined together by single and double bonds to form a hollow sphere with 12 pentagonal and 20 hexagonal faces—a design that resembles a football, or soccer ball.
In the trio was awarded the Nobel Prize for their pioneering efforts. The C60 molecule was named buckminsterfullerene or, more simply, the buckyball after the American architect R. Buckminster Fuller, whose geodesic dome is constructed on the same structural principles. Organic compounds containing bonds of carbon to nitrogen, oxygen and the halogens are not normally grouped separately.
Others are sometimes put into major groups within organic chemistry and discussed under titles such as organosulfur chemistry , organometallic chemistry , organophosphorus chemistry and organosilicon chemistry. Organic reactions are chemical reactions involving organic compounds. Many of these reactions are associated with functional groups. The general theory of these reactions involves careful analysis of such properties as the electron affinity of key atoms, bond strengths and steric hindrance. These factors can determine the relative stability of short-lived reactive intermediates , which usually directly determine the path of the reaction.
The basic reaction types are: addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions and redox reactions. An example of a common reaction is a substitution reaction written as:. The number of possible organic reactions is basically infinite.
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However, certain general patterns are observed that can be used to describe many common or useful reactions. Each reaction has a stepwise reaction mechanism that explains how it happens in sequence—although the detailed description of steps is not always clear from a list of reactants alone. The stepwise course of any given reaction mechanism can be represented using arrow pushing techniques in which curved arrows are used to track the movement of electrons as starting materials transition through intermediates to final products. Organic synthesis of a novel compound is a problem solving task, where a synthesis is designed for a target molecule by selecting optimal reactions from optimal starting materials.
Complex compounds can have tens of reaction steps that sequentially build the desired molecule. The synthesis proceeds by utilizing the reactivity of the functional groups in the molecule. For example, a carbonyl compound can be used as a nucleophile by converting it into an enolate , or as an electrophile ; the combination of the two is called the aldol reaction. Designing practically useful syntheses always requires conducting the actual synthesis in the laboratory. The scientific practice of creating novel synthetic routes for complex molecules is called total synthesis.
Strategies to design a synthesis include retrosynthesis , popularized by E. Corey , which starts with the target molecule and splices it to pieces according to known reactions. The pieces, or the proposed precursors, receive the same treatment, until available and ideally inexpensive starting materials are reached.