Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 1, Problem 1.9YT
Interpretation Introduction
Interpretation:
Notice the sum of the formal charges assigned in Solved Problem
Concept introduction:
In Solved Problem
Sum of the formal charges always equals the charge of the molecule.
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Below is the SN2 reaction between iodocyclohexane and cyanide (CN–). Draw the missing curved arrow notation in the first box to reflect electron movements. In both boxes, add lone pairs of electrons and nonzero formal charges.
Diazomethane has the formula H2CN2. Draw all valid resonance contributors for diazomethane and, using Table 1-3, propose which one contributes more to the resonance hybrid. Hint: There are no structures that avoid charged atoms.
In the following Lewis structure of [(CH3)2OH]+, 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).
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H-C-O-C-H
HHH
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H
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Η Η Η
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+
2+
2-
Chapter 1 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 1 - Prob. 1.1PCh. 1 - Prob. 1.2PCh. 1 - Prob. 1.3PCh. 1 - Prob. 1.4PCh. 1 - Prob. 1.5PCh. 1 - Prob. 1.6PCh. 1 - Prob. 1.7PCh. 1 - Prob. 1.8PCh. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Prob. 1.14PCh. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Prob. 1.27PCh. 1 - Prob. 1.28PCh. 1 - Prob. 1.29PCh. 1 - Prob. 1.30PCh. 1 - Prob. 1.31PCh. 1 - Prob. 1.32PCh. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Prob. 1.35PCh. 1 - Prob. 1.36PCh. 1 - Prob. 1.37PCh. 1 - Prob. 1.38PCh. 1 - Prob. 1.39PCh. 1 - Prob. 1.40PCh. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - Prob. 1.56PCh. 1 - Prob. 1.57PCh. 1 - Prob. 1.58PCh. 1 - Prob. 1.59PCh. 1 - Prob. 1.60PCh. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Prob. 1.68PCh. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Prob. 1.75PCh. 1 - Prob. 1.76PCh. 1 - Prob. 1.77PCh. 1 - Prob. 1.78PCh. 1 - Prob. 1.79PCh. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.1YTCh. 1 - Prob. 1.2YTCh. 1 - Prob. 1.3YTCh. 1 - Prob. 1.4YTCh. 1 - Prob. 1.5YTCh. 1 - Prob. 1.6YTCh. 1 - Prob. 1.7YTCh. 1 - Prob. 1.8YTCh. 1 - Prob. 1.9YTCh. 1 - Prob. 1.10YTCh. 1 - Prob. 1.11YTCh. 1 - Prob. 1.12YTCh. 1 - Prob. 1.13YTCh. 1 - Prob. 1.14YTCh. 1 - Prob. 1.15YTCh. 1 - Prob. 1.16YTCh. 1 - Prob. 1.17YT
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- The structure at the right is a skeleton of an anion having the overall formula C6H,NO¯. The hydrogen atoms are not shown. (a) Draw a complete Lewis structure in which the -1 formal charge is on N. Include all H atoms and C. valence electrons. (b) Do the same for a Lewis structure with the -1 formal charge on O. (c) Do the same for a Lewis structure with the -1 formal charge on the C atom that is bonded to three other C atoms.arrow_forwardIn the following Lewis structure of [(CH3)2OH]*, 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). H. H-C Н-С-О-С-Н C-H H HH 2- II 2-arrow_forwardDiazomethane (CH2N2) is an important reagent for the methylation of some organic molecules. Complete Parts 1 and 2 below about this unique reagent. Draw the Lewis structure of diazomethane (CH2N2) that contains a formal charge on carbon and nitrogen. Be sure to include all lone pairs of electrons and formal charges.arrow_forward
- Give typed full explanation Look at figure 3-22 that shows the electron density that occurs abound the Si-O bond. This electron density map gives the "shape" of the O and Si atoms when they are bonded together. Think about the answer in Q9 and choose the best response below: (Select answer choice) a. This figure shows that the Si and O atoms, when they bond together, do not form spheres, which is due to the fact that the Si-O bond is strongly covalent and these shared electrons affect atomic shape. This change in shape limits the applicability of Pauling's Coordination principle since that principle is based on the geometry of perfect spheres. b. This figure shows that the Si and O atoms, when they bond together are close to perfect spheres, which is due to the fact that the Si-O bond is strongly covalent. This figure shows that Pauling's Coordination principle should apply very precisely to any substance that contains Si-O bonds c. This figure shows that the Si and O atoms, form in a…arrow_forwardQ/ Three resonance structures of the highly unstable CSN – ion are shown below. a) Label any and all atomic formal charges that are present in each structure. b) Which of the structures is the major resonance structure? Why?arrow_forwardT 1C2: Draw multiple, valid resonance structures for line-angle structures using curved arrow notation and rank drawn resonance structures in order of their energy, stability, and contribution to the overall electronic nature of the structure. Fill in the data table with regard to the resonance structures given. Be sure to show all your important work for credit on this problem. Structure- Data Redraw Original Structure and Add Lone Pairs Redraw Original Structure with Lone Pairs and Add Curved Arrows to Neutralize as Many Formal Charges as Possible Draw Resonanc Structure That Follows From Curved Arrows Drawn Above ... Which Resonance Structure is Lower Energy (Original or Yours)? Why? HOO O OO OH CH3 O ✪ OH ⒸOH HOarrow_forward
- For the species below draw additional resonance structures (where all atoms have access to an octect of electrons) for species A, B, C, and D. Determine the bond order of the bond from the underlined C to underlined O for the lowest energy structure(s). You may need to evaluate the formal charge of the additional species you draw. These are species in an aprotic solvent, so only electrons may be moved, not hydrogen atoms. For each lettered structure below, input the bond order as an integer (1,2,etc) or improper fraction (4/3, 5/4, etc). A Structure Bond Order A HO: (f) H B B С Which structure A-D has the longest underlined C-O bond? :N=C=0: D Darrow_forward1) Draw the Lewis structure and all 5 possible resonance structures of the cyclopentadiene anion, C5H5-. Label all non-zero formal charges. (Hint: as the name suggests, the five carbons are arranged in cyclic (pentagonal) structure. As shown below. (10 points)arrow_forwardIn this problem I’m supposed to add the Hydrogens (originally not shown), valence electrons, and pi bonds to create C7H6NO- with a -1 formal charge on oxygen. This is what I got for this question and it keeps telling me it’s wrong. On the next part of the question it’s the same problem except the -1 formal charge is on the Nitrogen and I’m not sure how to draw that one either. Thank you!arrow_forward
- The Lewis structure for the chlorate ion is Calculate the formal charge on the chlorine (C1) atom. Express your answer as an integer. ► View Available Hint(s) formal charge on Cl = Submit Previous Answers Incorrect; Try Again; 3 attempts remaining Part B Calculate the formal charge on each of the oxygen (O) atoms labeled a, b, and c in the following Lewis structure. b :O: Express your answers as integers separated by commas. ► View Available Hint(s) b :0: formal charge on Oa, Ob, Oc c =arrow_forwardP2.9: Draw two different (minor) resonance contributors of the structure below (the flavin group of flavin adenine dinucleotide (FAD), a biochemical oxidation/reduction molecule) in which the oxygen indicated by an arrow bears a negative formal charge and one of the circled atoms bears a positive formal charge. Include curved arrows to account for the changing positions of electrons and pi bonds. R N Dolgt `N´ FAD H3C H3C Harrow_forwardProblem Draw a Lewis structure and identify the octet-rule exception for (a) H3PO4 (draw two resonance forms and select the more important); (b) BFCl2.Plan We draw each Lewis structure and examine it for exceptions to the octet rule.(a) The central atom is in Period 3, so it can have more than an octet.(b) The central atom is B, which can have fewer than an octet of electrons.arrow_forward
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