Concept explainers
(a)
Interpretation:
All resonance contributors for sulfuric acid
Concept introduction:
If a species having two or more valid Lewis structures, then its resonance structure exists. Resonance structures are imaginary; true species is represented by the resonance hybrid. The resonance structures are differed by the placement of their valence electrons, and not their atoms. Resonance structures with a greater number of atoms having an octet complete, more covalent bonds, and fewer atoms having a non-zero formal charge are considered to be stable. While drawing resonance structures curved arrows are used. The movement of a pair of electrons is indicated by a curved arrow. A curved arrow originates from a lone pair of electrons or from a covalent double or triple bond to indicate the specific pair of electrons that are being moved. The arrow points to an atom if the electrons being moved become a lone pair. Otherwise, the arrow points to the center of an existing bond to represent the formation of a new double/triple bond. A resonance structure can be drawn if a lone pair of electrons on an atom is adjacent with multiple bonds or an incomplete octet on an atom is adjacent to multiple bonds or there is a ring of alternating single and multiple bonds.
(b)
Interpretation:
Resonance hybrid for
Concept introduction:
A resonance hybrid structure is a weighted average structure of all the resonance contributors. A partial bond is represented in a resonance hybrid by a dashed line connecting the two atoms. In the resonance hybrid, the partial bonds are shown, which represent the atoms over which the electrons are delocalized. The resonance hybrid structure looks most like the lowest energy resonance structure and it is the most stable structure. The more stable resonance structures have a) a greater number of atoms having octet complete, b) more number of covalent bonds, and c) fewer atoms having a non-zero formal charge.
(c)
Interpretation:
The resonance structures of
Concept introduction:
A resonance hybrid structure is a weighted average structure of all the resonance contributors. A partial bond is represented in a resonance hybrid by a dashed line connecting the two atoms. In the resonance hybrid, the partial bonds are shown, which represent the atoms over which the electrons are delocalized. The resonance hybrid structure looks most like the lowest energy resonance structure and it is the most stable structure. The more stable resonance structures have a) a greater number of atoms having octet complete, b) more number of covalent bonds, and c) fewer atoms having a non-zero formal charge.
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Check out a sample textbook solutionChapter 1 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Draw all resonance structures for methylisocyanate, CH3NCO, a toxic gas used in the manufacturing of pesticides. Which resonance structures are the most important?arrow_forwardMethyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?arrow_forwardDraw the three resonance structures for (a) the cyanate ion (NCO−) and (b) the isocyanate ion (CNO−). In each case, rank the resonance structures in order of increasing importance. Be sure to include all lone pair electrons and nonzero formal charges.a) NCO−arrow_forward
- Which has a greater dipole moment? CH2Cl2 or CH2F2 The book states that a C-Cl bond has a greater dipole moment than a C-F bond, regardless of F's larger electronegativity, because the C-Cl has a larger bond length. Does the same logic apply?arrow_forwardCyanic acid, HOCN, and isocyanic acid, HNCO, dissolve in water to yield the same anion on loss of H+. Q.) Write a Lewis structure for isocyanic acidarrow_forwardwhat is the resonance stuctures for PO4 3-arrow_forward
- The curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.arrow_forward#1: What is the formal charge of bromine in the structure of bromate, BrO3-? a) 0 b) +1 c) +2 d) -1 #2: Carbonate (CO32-) has three resonance structures. Choose the stayement that best expains the meaning of those 3 resonance structures. a) Carbonate consists of two single CO bonds and one double CO bond. b) Carbonate consists of one single structure which is an average of the three resonance structures. c) Carbonate quickly flips back and forth between three structures. d) Three different structures for carbonate coexist. #3: When compaing a carbon-carbon double bond (C==C) and a carbon-carbon single bond (C-C), the double bond is a) longer and shorter b) longer and weaker c) shorter and stronger d) shorter and weakerarrow_forwardWould you expect the N-H bonds in NH3 to be polar? Why or why not?arrow_forward
- Is C3H7Br a polar molecule? If so, indicate the polarity of each bond and the direction of the net dipole.arrow_forwardCarbon monoxide (CO) has a very small dipole moment (0.122) despite having a polar C-O bond. Using resonance structures, please explain this conclusion.arrow_forwardRank the C-N bonds, A, B, C, in terms of decreasing bond strength.arrow_forward
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