Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 4, Problem 5CTQ
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Based on the atom connectivity shown bellow,evaluate the four resonance structure for the thiosulfate ion S2O3 ^2-.
Use curved arrows to indicate how you get from one resonance structure to another. Assign formal changes to all atoms and determine which of these resonance structure is the most stable based on a formal charge analysis
Explain your answer thoroughly. Look at the picture.
A resonance hybrid is a structure that can be depicted by more than one valid Lewis structure.
part1: Draw the major resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
part2: Draw the second most important resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
part3: Draw the least important resonance contributor for fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized and should include all nonzero formal charges and all nonbonding electrons.
A resonance hybrid is a structure that can be depicted by more than one valid Lewis structure.
part1: Draw the major resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
part2: Draw the second most important resonance form of fulminic acid, HCNO, with the atoms connected as indicated in the formula. Your structure should have nonzero formal charges minimized, and it should include all nonzero formal charges and all nonbonding electrons.
Chapter 4 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 4 - Prob. 1CTQCh. 4 - Figure 4.1 is a cartoon depiction of liquid water...Ch. 4 - Prob. 3CTQCh. 4 - Prob. 4CTQCh. 4 - In HF , neither H nor F holds a full formal charge...Ch. 4 - Prob. 6CTQCh. 4 - Prob. 7CTQCh. 4 - Prob. 8CTQCh. 4 - Within any one section of Table 4.2, boiling...Ch. 4 - Prob. 10CTQ
Ch. 4 - Prob. 11CTQCh. 4 - Prob. 12CTQCh. 4 - Prob. 13CTQCh. 4 - Prob. 14CTQCh. 4 - Prob. 15CTQCh. 4 - Prob. 16CTQCh. 4 - Prob. 17CTQCh. 4 - Prob. 18CTQCh. 4 - Prob. 19CTQCh. 4 - Prob. 20CTQCh. 4 - Prob. 21CTQCh. 4 - Prob. 22CTQCh. 4 - (E) Label each of the following as strong acid,...Ch. 4 - Prob. 24CTQCh. 4 - Draw the structure of the conjugate base of water....Ch. 4 - Does Cl have a conjugate acid? If so, what is it?...Ch. 4 - Draw the conjugate base of CH4 (methane).Ch. 4 - For the previous four questions, label each...Ch. 4 - Prob. 29CTQCh. 4 - According to the conventions above, what is the...Ch. 4 - Draw an arrow on Figure 4.13 representing Hrxn4 ....Ch. 4 - Prob. 32CTQCh. 4 - Add a + or above each curved arrow in Figure 4.11...Ch. 4 - Prob. 34CTQCh. 4 - Prob. 35CTQCh. 4 - Prob. 36CTQCh. 4 - Prob. 37CTQCh. 4 - Prob. 38CTQCh. 4 - Prob. 39CTQCh. 4 - Prob. 40CTQCh. 4 - Prob. 41CTQCh. 4 - Prob. 42CTQCh. 4 - Prob. 43CTQCh. 4 - Prob. 44CTQCh. 4 - Prob. 45CTQCh. 4 - Prob. 46CTQCh. 4 - For NH3 (ammonia) and H2O (water)... a. Use curved...Ch. 4 - Prob. 48CTQCh. 4 - Prob. 49CTQCh. 4 - Prob. 50CTQCh. 4 - Prob. 51CTQCh. 4 - Prob. 52CTQCh. 4 - Prob. 53CTQCh. 4 - Prob. 1ECh. 4 - Prob. 2ECh. 4 - Prob. 3ECh. 4 - Prob. 4ECh. 4 - Prob. 5ECh. 4 - Prob. 6ECh. 4 - Prob. 7ECh. 4 - Prob. 8ECh. 4 - Propanal (bp 48°C) and propanol (bp 97°C), both...Ch. 4 - Rank the following molecules from lowest to...Ch. 4 - Prob. 12ECh. 4 - For each molecule below, draw the conjugate acid...Ch. 4 - For each structure you drew in the answer to the...Ch. 4 - Mark each of the following statements True or...Ch. 4 - Organic chemistry is a bit like cooking. Later in...Ch. 4 - Prob. 17ECh. 4 - Prob. 18ECh. 4 - Are endothermic reactions favorable or...Ch. 4 - Prob. 20ECh. 4 - Is bond formation endothermic or exothermic? Write...Ch. 4 - Summarize the relationship between pKa and acid...Ch. 4 - Summarize the relationship between pKa and base...Ch. 4 - Prob. 25ECh. 4 - Consider the following bases: a. For each base...Ch. 4 - Prob. 27ECh. 4 - The following are equivalent ways of asking about...Ch. 4 - Prob. 29E
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- Indicate which of the following molecules are polar. Draw the molecular structure of each polar molecule, including the arrows that indicate the bond dipoles and the molecular dipole moment. (a) HCN (b) I2 (c) NOarrow_forwardDraw a Lewis structure for fulminic acid, HONC or HCNO, adding charges and lone electron pairs to the appropriate atoms. Explicitly draw all H atoms. Include all valence lone pairs in your answer. opy aste H-C=N=Qarrow_forwardIn the following Lewis structure of [SiF6]², every atom, bond and lone pair is positioned. To complete the structure, drag the formal charge tags to the appropriate atom(s). Each marker may be used more than once, or not at all. If an atom has a formal charge of zero, do not drag a tag to it. When you drag the marker in, place the little crosshairs in the upper left corner of the marker directly over the atom(s) in question (not above them). :F: :F : :ד: Si 1 :F: 0 0 0 2+ :H: Ë: 0 2-arrow_forward
- Describe the type of bond represented by the dash for each of the following compounds using the definitions in Q1. Consider only the atoms to which the dash is directly connected. H–H H–CH3 H–NH2 Na–ONa Na–Br K–OH H–OH H–Br F–CH3 Q4 Draw the electron-dot formulas for the following compounds or ions and calculate the formal charges for every atom. HF H2S F- Br+ N2 HCN NC-arrow_forwardSO < SO2< SO32-( a) Match each species with the number of covalent bonds predicted by Lewis structures to exist between an S atom and an O atom bonded to this S atom. (Hint: Average the number of bonds between S and an attached oxygen atom in a particular position using all of your resonance structures for the species that you are working on.)SO32- : is it 1.00, 1.33, 1.50, 2.00, 3.00 (b) Match each species with the correct formal charge on the central S atom. SO32- : is it -1.00 , -0.67 , -0.50, 0.00, +1.00, or +2.00 ? (c) Match each species with the average formal charge on an outside oxygen atom predicted by Lewis structures. SO32- : is it -1.00 , -0.67 , -0.50, 0.00, +1.00, or +2.00 ?arrow_forwardWhich 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_forward
- Arrange the highlighted bonds in the table below in decreasing order of polarity. That is, pick 1 for the most polar bond, pick 2 for the next most polar bond, and so on. bond polarity :F: (Choose one) (Choose one) |(Choose one)arrow_forwardUnshared, or lone, electron pairs play an important role in determining the chemical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. HC=CH aN b H The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c isarrow_forwardMake the following comparisons about the molecules shown next, and briefly explain your choices. Which molecule has the longer Al-C bond distance?arrow_forward
- Designate the structural features of polar molecules using partial charges or arrows. Ethyl heptanoate is responsible for grape aroma. It has the chemical formula C9H1802 but structural formula CH3-(CH2)s-COO-CH2-CH3. A structure is shown below. Which bonds would feature partial charges? Designate them using partial charges or arrows. H H H | H H H Harrow_forwardPure HN3 (atom sequence HNNN) is explosive. In aqueous solution, it is a weak acid that yields the azide ion, N3−. Draw one resonance structure for N3− and one resonance structure for HN3. Include all lone pair electrons and nonzero formal charges in your structures. helparrow_forwardSuppose that any given kind of bond, such as 0-H, has a characteristic electric dipole. That is, suppose that elec- tric dipole moments can be assigned to bonds just as bond energies can be. Both are usefully accurate approxi- mations. Consider the water molecule H `H Show that if MOH is the dipole moment of the OH bond, then the dipole moment of water is µ(H2O) = 2µ0H cos (0/2). What is the dipole moment µoH if µ(H,O) is 1.86 D?arrow_forward
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