Chemical synthesis

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In chemistry, chemical synthesis is the purposeful execution of one or more chemical reactions in order to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions. In modern laboratory usage, this tends to imply that the process is reproducible, reliable, and established to work in multiple laboratories.

A chemical synthesis begins by selection of compounds that are known as reagents or reactants. Various reaction types can be applied to these to synthesize the product, or an intermediate product. This requires mixing the compounds in a reaction vessel such as a chemical reactor or a simple round-bottom flask. Many reactions require some form of work-up procedure before the final product is isolated. The amount of product in a chemical synthesis is the reaction yield. Typically, chemical yields are expressed as a weight in grams or as a percentage of the total theoretical quantity of product that could be produced. A side reaction is an unwanted chemical reaction taking place that diminishes the yield of the desired product.

Contents

The word synthesis in its current meaning was first used by the chemist Adolph Wilhelm Hermann Kolbe.

Strategies

Many strategies exist in chemical synthesis that go beyond converting reactant A to reaction product B. In cascade reactions multiple chemical transformations take place within a single reactant, in multi-component reactions up to 11 different reactants form a single reaction product and in a telescopic synthesis one reactant goes through multiple transformations without isolation of intermediates.

Organic synthesis

Organic synthesis is a special branch of chemical synthesis dealing with the construction of organic compounds. It has developed into one of the most important components of organic chemistry. There are two main areas of research within the general area of organic synthesis: Total synthesis and methodology.

In the total synthesis of a complex product it may take multiple steps to synthesize the product of interest, and inordinate amounts of time. Skill in organic synthesis is prized among chemists and the synthesis of exceptionally valuable or difficult compounds has won chemists such as Robert Burns Woodward the Nobel Prize for Chemistry. If a chemical synthesis starts from basic laboratory compounds and yields something new, it is a purely synthetic process. If it starts from a product isolated from plants or animals and then proceeds to a new compounds, the synthesis is described as a semisynthetic process.

Total synthesis

A total synthesis[1] is the complete chemical synthesis of complex organic molecules from simple, commercially available (petrochemical) or natural precursors. In a linear synthesis there is a series of steps which are performed one after another until the molecule is made- this is often adequate for a simple structure. The chemical compounds made in each step are usually referred to as synthetic intermediates. For more complex molecules, a convergent synthesis is often preferred. This is where several "pieces" (key intermediates) of the final product are synthesized separately, then coupled together, often near the end of the synthesis.

The "father" of modern organic synthesis is regarded as Robert Burns Woodward, who received the 1965 Nobel Prize for Chemistry for several brilliant examples of total synthesis such as his 1954 synthesis of strychnine.[2] Some modern examples include Wender's, Holton's, Nicolaou's and Danishefsky's synthesis of Taxol.

Methodology

Each step of a synthesis involves a chemical reaction, and reagents and conditions for each of these reactions need to be designed to give a good yield and a pure product, with as little work as possible.[3] A method may already exist in the literature for making one of the early synthetic intermediates, and this method will usually be used rather than "trying to reinvent the wheel." However most intermediates are compounds that have never been made before, and these will normally be made using general methods developed by methodology researchers. To be useful, these methods need to give high yields and to be reliable for a broad range of substrates. Methodology research usually involves three main stages—discovery, optimisation, and studies of scope and limitations. The discovery requires extensive knowledge of and experience with chemical reactivities of appropriate reagents. Optimisation is where one or two starting compounds are tested in the reaction under a wide variety of conditions of temperature, solvent, reaction time, and so on, until the optimum conditions for product yield and purity are found. Then the researcher tries to extend the method to a broad range of different starting materials, to find the scope and limitations. Some larger research groups may then perform a total synthesis (see above) to showcase the new methodology and demonstrate its value in a real application.

Asymmetric synthesis

Many complex natural products occur as one pure enantiomer. Traditionally, however, a total synthesis could only make a complex molecule as a racemic mixture, that is, as an equal mixture of both possible enantiomer forms. The racemic mixture might then be separated via chiral resolution.

In the latter half of the twentieth century, chemists began to develop methods of asymmetric catalysis and kinetic resolution whereby reactions could be directed to produce only one enantiomer rather than a racemic mixture. Early examples include Sharpless epoxidation (K. Barry Sharpless) and asymmetric hydrogenation (William S. Knowles and Ryoji Noyori), and these workers went on to share the Nobel Prize in Chemistry in 2001 for their discoveries. Such reactions gave chemists a much wider choice of enantiomerically pure molecules to start from, where previously only natural starting materials could be used. Using techniques pioneered by Robert B. Woodward and new developments in synthetic methodology, chemists became more able to take simple molecules through to more complex molecules without unwanted racemisation, by understanding stereocontrol. This allowed the final target molecule to be synthesised as one pure enantiomer without any resolution being necessary. Such techniques are referred to as asymmetric synthesis.

Synthesis design

Elias James Corey brought a more formal approach to synthesis design, based on retrosynthetic analysis, for which he won the Nobel Prize for Chemistry in 1990. In this approach, the research is planned backwards from the product, using standard rules.[4] The steps are shown using retrosynthetic arrows (drawn as =>), which in effect means "is made from." Other workers in this area include one of the pioneers of computational chemistry, James B. Hendrickson, who developed a computer program for designing a synthesis based on sequences of generic "half-reactions." Computer-aided methods have recently been reviewed.[5]

Other meanings

The other meaning of chemical synthesis is narrow and restricted to a specific kind of chemical reaction, a direct combination reaction, in which two or more reactants combine to form a single product. The general form of a direct combination reaction is:

A + B → AB

where A and B are elements or compounds, and AB is a compound consisting of A and B. Examples of combination reactions include:

2Na + Cl2 → 2 NaCl (formation of table salt)
S + O2SO2 (formation of sulfur dioxide)
4 Fe + 3 O2 → 2 Fe2O3 (iron rusting)
CO2 + H2OH2CO3 (carbon dioxide dissolving and reacting with water to form carbonic acid)

General rules

4 special synthesis rules:

metal oxide + H2O → metal hydroxide
nonmetal oxide + H2O → oxy acid
metal chloride + O2 → metal chlorate
metal oxide + CO2 → metal carbonate

See also

Notes

  1. K.C. Nicolaou and E.J. Sorensen, Classics in Total Synthesis (New York: VCH, 1996).
  2. R.B. Woodward, M.P. Cava, W.D. Ollis, W. D. A. Hunger, H.U. Daeniker, and K. Schenker, The Total Synthesis of Strychnine, Journal of the American Chemical Society 76 (18): 4749–4751.
  3. J. March and D. Smith, Advanced Organic Chemistry, 5th (New York: Wiley, 2001).
  4. E. J. Corey and Xue-Min Cheng, The Logic of Chemical Synthesis (New York: John Wiley, 1999, ISBN 0471509795).
  5. Matthew H. Todd, Computer-aided Organic Synthesis, Chemical Society Reviews 34: 247–266.

References

  • Corey, E. J., and Xue-Min Cheng. 1995. The Logic of Chemical Synthesis. New York: John Wiley. ISBN 0471509795.
  • McMurry, John. 2004. Organic Chemistry, 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052.
  • Solomons, T.W. Graham, and Craig B. Fryhle. 2004. Organic Chemistry, 8th ed. Hoboken, NJ: John Wiley. ISBN 0471417998.
  • Vogel, A.I., et al. 1996. Vogel's Textbook of Practical Organic Chemistry, 5th Edition. Prentice Hall. ISBN 0582462363.
  • Zumdahl, Steven S. 2005. Chemical Principles. New York, NY: Houghton Mifflin. ISBN 0618372067.

External links

All links retrieved May 10, 2013.


Topics in organic chemistry

Aromaticity | Covalent bonding | Functional groups | Nomenclature | Organic compounds | Organic reactions | Organic synthesis | Publications | Spectroscopy | Stereochemistry

List of organic compounds

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