Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:(a) Draw all of the resonance structures of naphthalene. How many are there?
Ch.8 - Basic Concepts of Chemical Bonding
Chapter 8, Problem 59b
(b) Which of these compounds or ions is an exception to the octet rule: borohydride (BH4-), borazine (B3N3H6, which is analogous to benzene with alternating B and N in the ring), or boron trichloride?
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Identify the octet rule, which states that atoms tend to form compounds in ways that give them eight valence electrons, achieving a noble gas configuration.
Examine the structure of borohydride (BH4-): Boron typically forms three bonds, but in BH4-, it forms four bonds, achieving an octet by sharing electrons with hydrogen atoms.
Analyze borazine (B3N3H6): Boron and nitrogen alternate in a ring structure similar to benzene. Boron typically does not achieve a full octet in such structures, as it forms three bonds and has six valence electrons.
Consider boron trichloride (BCl3): Boron forms three bonds with chlorine atoms, resulting in only six valence electrons around boron, which is less than an octet.
Conclude that boron trichloride (BCl3) is an exception to the octet rule, as boron does not achieve a full octet in this compound.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Octet Rule
The octet rule is a chemical guideline stating that atoms tend to bond in such a way that they each have eight electrons in their valence shell, achieving a stable electron configuration similar to that of noble gases. This rule primarily applies to main group elements and helps predict the bonding behavior of atoms in molecules.
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Octet Rule
Electron Deficiency
Electron deficiency occurs when an atom does not have enough electrons to complete its octet, often seen in compounds with elements from group 13, such as boron. These compounds can form stable structures despite having fewer than eight electrons around the central atom, leading to exceptions to the octet rule.
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Electron Geometry
Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In compounds like borazine, resonance can help explain the stability and bonding characteristics that deviate from the octet rule, as the electrons are shared among multiple atoms rather than localized.
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Resonance Structures
Related Practice
Textbook Question
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Textbook Question
Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:
(b) Do you expect the C—C bond lengths in the molecule to be similar to those of C—C single bonds, C ═ C double bonds, or intermediate between C—C single and C ═ C double bonds?
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Textbook Question
Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:
(c) Not all of the C—C bond lengths in naphthalene are equivalent. Based on your resonance structures, how many C—C bonds in the molecule do you expect to be shorter than the others?
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Open Question
Draw the dominant Lewis structures for these chlorine–oxygen molecules/ions: ClO, ClO-, ClO2-, ClO3-, ClO4-. Which of these do not obey the octet rule?
Textbook Question
For Group 13–17 elements in the third row of the periodic table
and beyond, the octet rule is often not obeyed. A friend
of yours says this is because these heavier elements are more
likely to make double or triple bonds. Another friend of
yours says that this is because the heavier elements are larger
and can make bonds to more than four atoms at a time.
Which friend is more correct?
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Open Question
Draw the Lewis structures for each of the following ions or molecules. Identify those in which the octet rule is not obeyed; state which atom in each compound does not follow the octet rule; and state, for those atoms, how many electrons surround them: (a) HCl, (b) ICl5, (c) NO, (d) CF2Cl2, (e) I3-.