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Chapter 5.1: Representing Covalent Bonds

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    22849

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    Learning Objectives

    • To review the differences between covalent and ionic bonding.

    The atoms in all substances that contain more than one atom are held together by electrostatic interactionsAn interaction between electrically charged particles such as protons and electrons.—interactions between electrically charged particles such as protons and electrons. Electrostatic attractionAn electrostatic interaction between oppositely charged species (positive and negative) that results in a force that causes them to move toward each other. between oppositely charged species (positive and negative) results in a force that causes them to move toward each other, like the attraction between opposite poles of two magnets. In contrast, electrostatic repulsionAn electrostatic interaction between two species that have the same charge (both positive or both negative) that results in a force that causes them to repel each other. between two species with the same charge (either both positive or both negative) results in a force that causes them to repel each other, as do the same poles of two magnets. Atoms form chemical compounds when the attractive electrostatic interactions between them are stronger than the repulsive interactions. Collectively, we refer to the attractive interactions between atoms as chemical bondsAn attractive interaction between atoms that holds them together in compounds..

    Chemical bonds are generally divided into two fundamentally different kinds: ionic and covalent. In reality, however, the bonds in most substances are neither purely ionic nor purely covalent, but they are closer to one of these extremes. Although purely ionic and purely covalent bonds represent extreme cases that are seldom encountered in anything but very simple substances, a brief discussion of these two extremes helps us understand why substances that have different kinds of chemical bonds have very different properties. Ionic compoundsA compound consisting of positively charged ions (cations) and negatively charged ions (anions) held together by strong electrostatic forces. consist of positively and negatively charged ions held together by strong electrostatic forces, whereas covalent compoundsA compound that consists of discrete molecules. generally consist of moleculesA group of atoms in which one or more pairs of electrons are shared between bonded atoms., which are groups of atoms in which one or more pairs of electrons are shared between bonded atoms. In a covalent bondThe electrostatic attraction between the positively charged nuclei of the bonded atoms and the negatively charged electrons they share., the atoms are held together by the electrostatic attraction between the positively charged nuclei of the bonded atoms and the negatively charged electrons they share. We begin our review of structures and formulas by describing covalent compounds. 

    Note the Pattern

    Ionic compounds consist of ions of opposite charges held together by strong electrostatic forces, whereas pairs of electrons are shared between bonded atoms in covalent compounds.

    Covalent Molecules and Compounds

    Just as an atom is the simplest unit that has the fundamental chemical properties of an element, a molecule is the simplest unit that has the fundamental chemical properties of a covalent compound. Some pure elements exist as covalent molecules. Hydrogen, nitrogen, oxygen, and the halogens occur naturally as the diatomic (“two atoms”) molecules H2, N2, O2, F2, Cl2, Br2, and I2 (part (a) in Figure 6.1.1). Similarly, a few pure elements are polyatomicMolecules that contain more than two atoms. (“many atoms”) molecules, such as elemental phosphorus and sulfur, which occur as P4 and S8 (part (b) in Figure 5.1.1 ).

    Each covalent compound is represented by a molecular formulaA representation of a covalent compound that consists of the atomic symbol for each component element (in a prescribed order) accompanied by a subscript indicating the number of atoms of that element in the molecule. The subscript is written only if the number is greater than 1., which gives the atomic symbol for each component element, in a prescribed order, accompanied by a subscript indicating the number of atoms of that element in the molecule. The subscript is written only if the number of atoms is greater than 1. For example, water, with two hydrogen atoms and one oxygen atom per molecule, is written as H2O. Similarly, carbon dioxide, which contains one carbon atom and two oxygen atoms in each molecule, is written as CO2.

    Figure 5.1.1 Elements That Exist as Covalent Molecules

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    (a) Several elements naturally exist as diatomic molecules, in which two atoms (E) are joined by one or more covalent bonds to form a molecule with the general formula E2. (b) A few elements naturally exist as polyatomic molecules, which contain more than two atoms. For example, phosphorus exists as P4 tetrahedra—regular polyhedra with four triangular sides—with a phosphorus atom at each vertex. Elemental sulfur consists of a puckered ring of eight sulfur atoms connected by single bonds. Selenium is not shown due to the complexity of its structure.

    Covalent compounds that contain predominantly carbon and hydrogen are called organic compoundsA covalent compound that contains predominantly carbon and hydrogen.. One convention for representing the formulas of organic compounds is to write carbon first, followed by hydrogen and then any other elements in alphabetical order (e.g., CH4O is methyl alcohol, a fuel).  Another convention better represents the molecular structure as a structural formula, as, for example, writing the formula for methyl alcohol asCH 3OH, where CH3 is the methyl group and OH the hydroxyl.  Compounds that consist primarily of elements other than carbon and hydrogen are called inorganic compoundsAn ionic or covalent compound that consists primarily of elements other than carbon and hydrogen.; they include both covalent and ionic compounds. In inorganic compounds, the component elements are listed beginning with the one farthest to the left in the periodic table, such as we see in CO2 or SF6. Those in the same group are listed beginning with the lower element and working up, as in ClF. By convention, however, when an inorganic compound contains both hydrogen and an element from groups 13–15, the hydrogen is usually listed last in the formula. Examples are ammonia (NH3) and silane (SiH4). Compounds such as water, whose compositions were established long before this convention was adopted, are always written with hydrogen first: Water is always written as H2O, not OH2. The conventions for inorganic acids, such as hydrochloric acid (HCl) and sulfuric acid (H2SO4), are described in Section 8.6.

    Note the Pattern

    For organic compounds: write C first, then H, and then the other elements in alphabetical order. For molecular inorganic compounds: start with the element at far left in the periodic table; list elements in same group beginning with the lower element and working up.

    Example 1

    Write the molecular formula of each compound.

    1. The phosphorus-sulfur compound that is responsible for the ignition of so-called strike anywhere matches has 4 phosphorus atoms and 3 sulfur atoms per molecule.
    2. Ethyl alcohol, the alcohol of alcoholic beverages, has 1 oxygen atom, 2 carbon atoms, and 6 hydrogen atoms per molecule.
    3. Freon-11, once widely used in automobile air conditioners and implicated in damage to the ozone layer, has 1 carbon atom, 3 chlorine atoms, and 1 fluorine atom per molecule.

    Given: identity of elements present and number of atoms of each

    Asked for: molecular formula

    Strategy:

    A Identify the symbol for each element in the molecule. Then identify the substance as either an organic compound or an inorganic compound.

    B If the substance is an organic compound, arrange the elements in order beginning with carbon and hydrogen and then list the other elements alphabetically. If it is an inorganic compound, list the elements beginning with the one farthest left in the periodic table. List elements in the same group starting with the lower element and working up.

    C From the information given, add a subscript for each kind of atom to write the molecular formula.

    Solution:

    1. A The molecule has 4 phosphorus atoms and 3 sulfur atoms. Because the compound does not contain mostly carbon and hydrogen, it is inorganic. B Phosphorus is in group 15, and sulfur is in group 16. Because phosphorus is to the left of sulfur, it is written first. C Writing the number of each kind of atom as a right-hand subscript gives P4S3 as the molecular formula.
    2. A Ethyl alcohol contains predominantly carbon and hydrogen, so it is an organic compound. B The formula for an organic compound is written with the number of carbon atoms first, the number of hydrogen atoms next, and the other atoms in alphabetical order: CHO. C Adding subscripts gives the molecular formula C2H6O.  To convey more structural information we could write this as C2H5OH.  Draw the Lewis structure using this information
    3. A Freon-11 contains carbon, chlorine, and fluorine. It can be viewed as either an inorganic compound or an organic compound (in which fluorine has replaced hydrogen). The formula for Freon-11 can therefore be written using either of the two conventions.

      B According to the convention for inorganic compounds, carbon is written first because it is farther left in the periodic table. Fluorine and chlorine are in the same group, so they are listed beginning with the lower element and working up: CClF. Adding subscripts gives the molecular formula CCl3F.

      C We obtain the same formula for Freon-11 using the convention for organic compounds. The number of carbon atoms is written first, followed by the number of hydrogen atoms (zero) and then the other elements in alphabetical order, also giving CCl3F.

    Exercise

    Write the molecular formula for each compound.

    1. Nitrous oxide, also called “laughing gas,” has 2 nitrogen atoms and 1 oxygen atom per molecule. Nitrous oxide is used as a mild anesthetic for minor surgery and as the propellant in cans of whipped cream.
    2. Sucrose, also known as cane sugar, has 12 carbon atoms, 11 oxygen atoms, and 22 hydrogen atoms.
    3. Sulfur hexafluoride, a gas used to pressurize “unpressurized” tennis balls and as a coolant in nuclear reactors, has 6 fluorine atoms and 1 sulfur atom per molecule.

    Answer:

    1. N2O
    2. C12H22O11
    3. SF6

    Representations of Molecular Structures

    Molecular formulas give only the elemental composition of molecules. In contrast, structural formulasA representation of a molecule that shows which atoms are bonded to one another and, in some cases, the approximate arrangement of atoms in space. show which atoms are bonded to one another and, in some cases, the approximate arrangement of the atoms in space. These are the Lewis structures we learned about.  Knowing the structural formula of a compound enables chemists to create a three-dimensional model, which provides information about how that compound will behave physically and chemically.

    The structural formula for H2 can be drawn as H–H and that for I2 as I–I, where the line indicates a single pair of shared electrons, a single bondA chemical bond formed when two atoms share a single pair of electrons.. Two pairs of electrons are shared in a double bondA chemical bond formed when two atoms share two pairs of electrons., which is indicated by two lines— for example, O2 is O=O. Three electron pairs are shared in a triple bondA chemical bond formed when two atoms share three pairs of electrons., which is indicated by three lines—for example, N2 is N≡N (see Figure 5.1.2). Carbon is unique in the extent to which it forms single, double, and triple bonds to itself and other elements. The number of bonds formed by an atom in its covalent compounds is not arbitrary. As we have learned in Chapter 4, hydrogen, oxygen, nitrogen, and carbon have a very strong tendency to form substances in which they have one, two, three, and four bonds to other atoms, respectively (Figure 5.1.2).

    Figure 5.1.2 Molecules That Contain Single, Double, and Triple Bonds

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    Hydrogen (H2) has a single bond between atoms. Oxygen (O2) has a double bond between atoms, indicated by two lines (=). Nitrogen (N2) has a triple bond between atoms, indicated by three lines (≡). Each bond represents an electron pair.

    Table  5.1.1 The Number of Bonds That Selected Atoms Commonly Form to Other Atoms

    Atom Number of Bonds
    H (group 1) 1
    O (group 16) 2
    N (group 15) 3
    C (group 14) 4

     

    Example 2

    Write the molecular formula for each compound. The condensed structural formula is given.

    1. Sulfur monochloride (also called disulfur dichloride) is a vile-smelling, corrosive yellow liquid used in the production of synthetic rubber. Its condensed structural formula is ClSSCl.
    2. Ethylene glycol is the major ingredient in antifreeze. Its condensed structural formula is HOCH2CH2OH.
    3. Trimethylamine is one of the substances responsible for the smell of spoiled fish. Its condensed structural formula is (CH3)3N.

    Given: condensed structural formula

    Asked for: molecular formula

    Strategy:

    A Identify every element in the condensed structural formula and then determine whether the compound is organic or inorganic.

    B As appropriate, use either organic or inorganic convention to list the elements. Then add appropriate subscripts to indicate the number of atoms of each element present in the molecular formula.

    Solution:

    The molecular formula lists the elements in the molecule and the number of atoms of each.

    1. A Each molecule of sulfur monochloride has two sulfur atoms and two chlorine atoms. Because it does not contain mostly carbon and hydrogen, it is an inorganic compound. B Sulfur lies to the left of chlorine in the periodic table, so it is written first in the formula. Adding subscripts gives the molecular formula S2Cl2.
    2. A Counting the atoms in ethylene glycol, we get six hydrogen atoms, two carbon atoms, and two oxygen atoms per molecule. The compound consists mostly of carbon and hydrogen atoms, so it is organic. B As with all organic compounds, C and H are written first in the molecular formula. Adding appropriate subscripts gives the molecular formula C2H6O2.
    3. A The condensed structural formula shows that trimethylamine contains three CH3 units, so we have one nitrogen atom, three carbon atoms, and nine hydrogen atoms per molecule. Because trimethylamine contains mostly carbon and hydrogen, it is an organic compound. B According to the convention for organic compounds, C and H are written first, giving the molecular formula C3H9N.
    492434289500ceeff1a9b849c03ff476.jpg

    Exercise

    Write the molecular formula for each molecule.

    1. Chloroform, which was one of the first anesthetics and was used in many cough syrups until recently, contains one carbon atom, one hydrogen atom, and three chlorine atoms. Its condensed structural formula is CHCl3.
    2. Hydrazine is used as a propellant in the attitude jets of the space shuttle. Its condensed structural formula is H2NNH2.
    3. Putrescine is a pungent-smelling compound first isolated from extracts of rotting meat. Its condensed structural formula is H2NCH2CH2CH2CH2NH2. This is often written as H2N(CH2)4NH2 to indicate that there are four CH2 fragments linked together.
    11f33c05de3236faf69f2abd2098484a.jpg

    Answer:

    1. CHCl3
    2. N2H4
    3. C4H12N2

    Summary

    The atoms in chemical compounds are held together by attractive electrostatic interactions known as chemical bonds.  Most covalent compounds consist of molecules, groups of atoms in which one or more pairs of electrons are shared by at least two atoms to form a covalent bond. The atoms in molecules are held together by the electrostatic attraction between the positively charged nuclei of the bonded atoms and the negatively charged electrons shared by the nuclei. The molecular formula of a covalent compound gives the types and numbers of atoms present. Compounds that contain predominantly carbon and hydrogen are called organic compounds, whereas compounds that consist primarily of elements other than carbon and hydrogen are inorganic compounds. Diatomic molecules contain two atoms, and polyatomic molecules contain more than two. A structural formula indicates the composition and approximate structure and shape of a molecule. Single bonds, double bonds, and triple bonds are covalent bonds in which one, two, and three pairs of electrons, respectively, are shared between two bonded atoms. Covalent molecular compounds, consist of discrete molecules held together by weak intermolecular forces and can be gases, liquids, or solids at room temperature and pressure.

    Key Takeaway

    • There are two fundamentally different kinds of chemical bonds (covalent and ionic) that cause substances to have very different properties.

    Conceptual Problems

    1. Ionic and covalent compounds are held together by electrostatic attractions between oppositely charged particles. Describe the differences in the nature of the attractions in ionic and covalent compounds. Which class of compounds contains pairs of electrons shared between bonded atoms?

    2. What is the difference between an organic compound and an inorganic compound?

    3. What is the advantage of writing a structural formula as a condensed formula?

    4. The majority of elements that exist as diatomic molecules are found in one group of the periodic table. Identify the group.

    5. Discuss the differences between covalent and ionic compounds with regard to

      1. the forces that hold the atoms together.
      2. melting points.
      3. physical states at room temperature and pressure.
    6. Why do covalent compounds generally tend to have lower melting points than ionic compounds?

    Answer

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    7. Covalent compounds generally melt at lower temperatures than ionic compounds because the intermolecular interactions that hold the molecules together in a molecular solid are weaker than the electrostatic attractions that hold oppositely charged ions together in an ionic solid.

    Numerical Problems

    1. The structural formula for chloroform (CHCl3) was shown in Example 2. Based on this information, draw the structural formula of dichloromethane (CH2Cl

    Answers

    1.  

    Contributors

    • Anonymous

    Modified by Joshua Halpern