Organic Chemistry Chapter 1 Structure and Properties

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(Page 3) (1.) 1.1 Organic chemistry Organic chemistry is the chemistry of the compounds of carbon.
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(Page 3) (2.) The misleading name “organic” is a relic of the days when chemical compounds were divided into two classes, inorganic and organic, depending upon where they had come from.
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(Page 3) (3.) Inorganic compounds were those obtained from minerals: organic compounds were those obtained from vegetable or animal sources, that is, from material produced by living organisms.
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(Page 3) (4.) Indeed, until about 1850 many chemists believed that organic compounds must have their origin in living organisms, and consequently could never be synthesized from inorganic material.
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(Page 3) (5.) These compounds from organic sources had this in common: they all contained the element carbon.
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(Page 3) (6.) Even after it had become clear that these compounds did not have to come from living sources but could be made in the laboratory, it was convenient to keep the name organic to describe them and compounds like them.
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(Page 3) (7.) The division between inorganic and organic compounds has been retained to this day.
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(Page 3) (8.) Today, although many compounds of carbon are still most conveniently isolated from plant and animal sources, most of them are synthesized.
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(Page 3) (9.) They are sometimes synthesized from inorganic substances like carbonates or cyanides, but more often from other organic compounds.
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(Page 3) (10.) There are two large reservoirs of organic material from which simple organic compounds can be obtained: petroleum and coal.
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(Page 3) (11.) “Both of these are “organic” in the old sense, being products of the decay of plants and animals.”
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(Page 3) (12.) These simple compounds are used as building blocks from which larger and more complicated compounds can be made.
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(Page 3) (13.) We recognize petroleum and coal as the fossil fuels, laid down over millennia and non-renewable. They–particularly petroleum– are being consumed at an alarming rate to meet our constantly increasing demands for power.
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(Page 3) (14.) Today, less than ten percent of the petroleum used goes into making chemicals; most of it is simply burned to supply energy. (Page 4) There are, fortunately, alternative sources of power–solar,
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(Page 4) (15.) geothermal, wind, waves, tides, nuclear energy–but where are we to find an alternative reservoir of organic raw material? Eventually, of course, we shall have to go to the place where the fossil fuels originally came from–the biomass–but this time directly, without the intervening millennia.
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(Page 4) (16.) The biomass is renewable and, used properly, can last as long on this planet as we can. In the meantime, it has been suggested, petroleum is too valuable to burn. What is so special about the compounds of carbon that they should be separated from compounds of
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(Page 4) (17) all the other hundred-odd elements of the Periodic Table? In part, at least, the answer seems to be this: there are so very many compounds of carbon, and their molecules can be so large and complex. The number of compounds that contain carbon is many
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(Page 4) (18) times greater than the number of compounds that do not contain carbon. These organic compounds have been divided into families, which generally have no counterparts among the inorganic compounds.
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(Page 4) (19) Organic molecules containing thousands of atoms are known, and the arrangement of atoms in even relatively small molecules can be very complicated.
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(Page 4) (20) One of the major problems in organic chemistry is to find out how the atoms are arranged in molecules, that is, to determine the structures of compounds.
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(Page 4) (21) There are many ways in which these complicated molecules can break apart, or rearrange themselves, to form new molecules; there are many ways in which atoms can be added to these molecules, or new atoms substituted for old ones.
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(Page 4) (22) Much of organic chemistry is devoted to finding out what these reactions are, how they take place, and how they can be used to synthesize compounds we want.
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(Page 4) (23) What is so special about carbon that it should form so many compounds?
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(Page 4) (24) The answer to this question came to August KeKulé in 1854 during a London bus ride.
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(Page 4) (25) “One fine summer evening, I was returning by the last omnibus, ‘outside’ as usual, through the deserted streets of the metropolis, which are at other times so full of life.
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(Page 4) (26) I fell into a reverie and lo! the atoms were gambolling before my eyes…
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(Page 4) (27) I saw how, frequently, two smaller atoms united to form a pair, how a larger one embraced 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.
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(Page 4) (28) I saw how the larger ones formed a chain…I spent part of the night putting on paper at least sketches of these dream forms.” –August KekulĂ©, 1890.
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(Page 4) (29) Carbon atoms can attach themselves to one another to an extent not possible for atoms of any other element.
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(Page 4) (30) Carbon atoms can form chains thousands of atoms long, or rings of all sizes; the chains and rings can have branches and cross-links.
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(Page 4) (31) To the carbon atoms of these chains and rings there are attached other atoms, chiefly hydrogen, but also fluorine, chlorine, bromine, iodine, oxygen, nitrogen, sulfur, phosphorus, and many others.
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(Page 4) (32) Each different arrangement of atoms corresponds to a different compound, and each compound has its own characteristic set of chemical and physical properties.
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(Page 4) (33) It is not surprising that more than ten million compounds of carbon are known today and that this number is growing by half a million a year.
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.(Page 4) (34) It is not surprising that the study of their chemistry is a special field. Organic chemistry is a field of immense importance to technology:
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(Page 4) (35) it is the chemistry of dyes and drugs, paper and ink, paints and plastics, gasoline and rubber tires;
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(Page 4) (36) it is the chemistry of the food we eat and the clothing we wear.
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(Page 4) (37) Organic chemistry is fundamental to biology and medicine.
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(Page 4) (38) Aside from water, living organisms are made up chiefly of organic compounds; the molecules of “molecular biology” are organic molecules.
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To me it appears like a primeval tropical forest full of the most remarkable things, a dreadful endless jungle into which one does not dare enter for there seems to be no way out.”–Friedrich Wöhler, 1835
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How can we even begin to study a subject of such enormous complexity?
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(Page 5) It is not farfetched to say that we are living in the Age of Carbon.
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Every day the newspapers bring to our attention compounds of carbon: cholesterol and polyunsaturated fats, growth hormones and steroids, insecticides and pheromones, carcinogens and chemotherapeutic agents, DNA and genes.
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Page 5 Wars are fought over petroleum. Twin catastrophes threaten us, both arising from the accumulation of compounds of carbon in the atmosphere: depletion of the ozone layer, due chiefly to the chlorofluorocarbons; and the greenhouse effect, due to methane, chlorofluorocarbons, and, most of all, carbon dioxide.
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It is perhaps symbolic that for 1990 the journal Science selected as the molecule of the year diamond, one of the allotropic forms of carbon.
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Page 5 And for 1991 the choice was another newly discovered allotrope of carbon, C60 buckminsterfullerene—which has generated excitement in the chemical world not seen, it has been said, “since the days of KekulĂ©.”
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Page 5 1.2 Structures and properties of molecules The properties of a substance depend on the atoms it contains and also on the bond connectivity of these constituting atoms.
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It is the basis upon which these facts can best be accounted for and understood.
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The structural theory is the framework of ideas about how atoms are put together to make molecules.
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The structural theory has to do with the order in which atoms are attached to each other, and with the electrons that hold them together.
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It has to do with the shapes and sizes of the molecules that these atoms form, and with the way that electrons are distributed over them.
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A molecule is often represented by a picture or a model–sometimes by several pictures or several models.
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The atomic nuclei are represented by letters or wooden balls, and the electrons that join them by lines or dots or wooden pegs.
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These crude pictures and models are useful to us only if we understand what they are intended to mean.
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Interpreted in terms of the structural theory, they tell us a good deal about the compound whose molecules they represent: how to go about making it;
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what physical properties to expect of it–melting point, boiling point, specific gravity, the kind of solvents the compound will dissolve in , even whether it will be colored or not;
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what kind of chemical behavior to expect–the kind of reagents the compound will react with and the kind of products that will be formed, whether it will react rapidly or slowly.
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We would know all this about a compound that we had never encountered before, simply on the basis of its structural formula and what we understand its structural formula to mean.
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The chemical bond before 1926
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Any consideration of the structure of molecules must begin with a discussion of chemical bonds, the forces that hold atoms together in a molecule.
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We shall discuss chemical bonds first in terms of the theory as it had developed prior to 1926 and then in terms of the theory of today.
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The introduction of quantum mechanics in 1926 caused a tremendous change in ideas about how molecules are formed.
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For convenience, the older, simpler language and pictorial representations are often still used, although the words and pictures are given a modern interpretation.
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In 1916 two kinds of chemical bond were described: the ionic bond by Walther Kossel “in Germany” and the covalent bond by G. N. Lewis “of the University of California”.
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Both Kossel and Lewis based their ideas on the following concept of the atom.
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A positively charged nucleus is surrounded by electrons arranged in concentric shells or energy levels.
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There is a maximum number of electrons that can be accommodated in each shell: two in the first shell, eight in the second shell, eight or eighteen in the third shell, and so on.
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The greatest stability is reached when the outer shell is full, as in the noble gases.
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Both ionic and covalent bonds arise from the tendency of atoms to attain this stable configuration of electrons.
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The ionic bond results from transfer of electrons, as, for example, in the formation of lithium fluoride.
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A lithium atom has two electrons in its inner shell
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and one electron in its outer or valence shell: the loss of one electron would leave lithium with a full outer shell of two electrons.
and one electron in its outer or valence shell: the loss of one electron would leave lithium with a full outer shell of two electrons.
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A fluorine atom has two electrons in its inner shell and seven electrons in its valence shell; the gain of one electron would give fluorine a full outer shell of eight.
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Lithium fluoride is formed by the transfer of one electron from lithium to fluorine: lithium n ow bears a positive charge and fluorine bears a negative charge.
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The electrostatic attraction between the oppositely charged ions is called an ionic bond.
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Such ionic bonds are typical of the salts formed by combination of the metallic elements “electropositive elements” on the far left side of the Periodic Table. with the non-metallic elements “electronegative elements” on the far right side.
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The covalent bond results from sharing of electrons, as, for example, in the formation of the hydrogen molecule. Each hydrogen atom has a single electron; by sharing a pair of electrons, both hydrogens can complete their shells of two.
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Two fluorine atoms, each with seven electrons in the valence shell, can complete their octets by sharing a pair of electrons.
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In a similar way we can visualize the formation HF, H2O, NH, CH4, and CF4.
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Here too, the bonding force is electrostatic attraction:
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this time between each electron and both nuclei.
this time between each electron and both nuclei.
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The covalent bond is typical of the compounds of carbon; it is the bond of chief importance in the study of organic chemistry.
The covalent bond is typical of the compounds of carbon; it is the bond of chief importance in the study of organic chemistry.
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