Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 13E
Complete each Lewis structure, draw all important resonance structures, predict a value for thebond angles requested, and explain your reasoning.
a. Nitrous acid
b. Enolate ion
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Oxalic acid (H₂C₂O4) has the following structure:
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H—Ö—C—C—ö—h
An oxalic acid solution contains H₂C₂O4, HC₂04, C₂0, and H* in varying concentrations.
Part 1 of 5
Draw the best Lewis structure of HC204. Include lone pair electrons and any formal charges.
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Draw one BEST Lewis structure for the generic molecule XY4Z. Don't worry about resonance structures. Include all formal charges.
Element X is the least electronegative. EN values: X = 3.0, Y = 3.5, Z = 4.0.
For neutral atoms, element X has 8 valence electrons and element Y has 7, and Z has 6.
The highest occupied principal energy level of the central atom is greater than 2.
Is the measured/approximate bond angle(s) equal to, less than, or greater than the angle predicted by VSEPR theory? Briefly explain why (in ~1 sentence).
Draw the best wedge-dash structure and add dipole moments (if applicable). If there is a net dipole moment, draw it. If not, write “nonpolar."
Draw Lewis structure(s) for the carbonate lon (CO₂). If there are equivalent resonance structures, draw all of them.
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Draw one structure per sketcher box, and separate added sketcher boxes with the symbol.
Do not include overall lon charges or formal charges in your drawing.
Do not draw double bonds to oxygen unless they are needed in order for the central atom to obey the octet rule.
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b Draw Lewis structure(s) for the acetaldehyde molecule (CH₂CHO). If there are equivalent resonance structures, draw all of the
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Do not include overall ion charges or formal charges in your drawing.
Do not draw double bonds to oxygen unless they are needed in order for the central atom to obey the octet rule.
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Chapter 5 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 5 - Which elements on the periodic table (other than...Ch. 5 - You will not find “hydroxide” in the stockroom,...Ch. 5 - Prob. 3CTQCh. 5 - Prob. 4CTQCh. 5 - Prob. 5CTQCh. 5 - Prob. 6CTQCh. 5 - On which do you expect to have a more intense and...Ch. 5 - Prob. 8CTQCh. 5 - Prob. 9CTQCh. 5 - Prob. 10CTQ
Ch. 5 - Prob. 11CTQCh. 5 - Prob. 12CTQCh. 5 - Prob. 13CTQCh. 5 - Prob. 14CTQCh. 5 - Prob. 15CTQCh. 5 - Prob. 16CTQCh. 5 - For each proposed set of resonance structures: a....Ch. 5 - Consider the polarization of the C=O bond in the...Ch. 5 - The C=O double bond is called a “carbonyl bond.”...Ch. 5 - Prob. 20CTQCh. 5 - Prob. 21CTQCh. 5 - Prob. 22CTQCh. 5 - Prob. 23CTQCh. 5 - Prob. 24CTQCh. 5 - Prob. 25CTQCh. 5 - Prob. 26CTQCh. 5 - Prob. 27CTQCh. 5 - Prob. 28CTQCh. 5 - Prob. 29CTQCh. 5 - Prob. 30CTQCh. 5 - Prob. 31CTQCh. 5 - Confirm that there is no legitimate Lewis...Ch. 5 - Draw all resonance structures of the molecule...Ch. 5 - Prob. 34CTQCh. 5 - Prob. 35CTQCh. 5 - Prob. 36CTQCh. 5 - Occasionally, we will see an ionic compound that...Ch. 5 - Prob. 2ECh. 5 - Prob. 3ECh. 5 - Prob. 4ECh. 5 - Is it possible to draw a resonance structure of...Ch. 5 - Prob. 6ECh. 5 - Prob. 7ECh. 5 - Prob. 8ECh. 5 - Phenol (shown below) has a pKa10 . a. Based on pKa...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Prob. 12ECh. 5 - Complete each Lewis structure, draw all important...Ch. 5 - Use curved arrows to show the most likely...Ch. 5 - Construct an explanation for why sulfuric acid is...Ch. 5 - Prob. 16ECh. 5 - Prob. 17ECh. 5 - Prob. 18E
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider the pyrosulfate ion, S2O72-. It has no sulfur–sulfur nor oxygen–oxygen bonds. (a) Write a Lewis structure for the pyrosulfate ion using only single bonds. (b) What is the formal charge on the sulfur atoms for the Lewis structure you drew in part (a)? (c) Write another Lewis structure using six bonds and two O—S bonds. (d) What is the formal charge on each atom for the structure you drew in part (c)?arrow_forwardThe chemistry of the nitrite ion and HNO2: (a) Two resonance structures are possible for NO2. Draw these structures, and then find the formal charge on each atom in each resonance structure. (b) In forming the acid HNO2 an H+ ion attaches to the O atom and not the N atom of NO2. Explain why you would predict this result. (c) Two resonance structures are possible for HNO2. Draw these structures, and then find the formal charge on each atom in each resonance structure. Is either of these structures strongly preferred over the other?arrow_forwardThe electrostatic potential surface for SOCl2 is pictured here. (a) Draw a Lewis electron dot picture for the molecule, and give the formal charge of each atom. (b) What is the molecular geometry of SOCl2? Is it polar?arrow_forward
- Molecules in space: (a) In addition to molecules such as CO, HCl, H2O, and NH3, glycolaldehyde has been detected in outer space. Is the molecule polar? (b) Where do the positive and negative charges lie in the molecule? (c) One molecule found in the 1995 Hale-Bopp comet is HC3N. Suggest a structure for this molecule.arrow_forwardEach compound contains both ions and covalent bonds. Draw the Lewis structure for each compound. Show with dashes which are covalent bonds and show with charges which are ions. (a) Sodium methoxide, CH3ONa (b) Ammonium chloride, NH4Cl (c) Sodium bicarbonate, NaHCO3 (d) Sodium borohydride, NaBH4 (e) Lithium aluminum hydride, LiAlH4arrow_forwardBond Enthalpy When atoms of the hypothetical element X are placed together, they rapidly undergo reaction to form the X2 molecule: X(g)+X(g)X2(g) a Would you predict that this reaction is exothermic or endothermic? Explain. b Is the bond enthalpy of X2 a positive or a negative quantity? Why? c Suppose H for the reaction is 500 kJ/mol. Estimate the bond enthalpy of the X2 molecule. d Another hypothetical molecular compound, Y2(g), has a bond enthalpy of 750 kJ/mol, and the molecular compound XY(g) has a bond enthalpy of 1500 kJ/mol. Using bond enthalpy information, calculate H for the following reaction. X2(g)+Y2(g)2XY(g) e Given the following information, as well as the information previously presented, predict whether or not the hypothetical ionic compound AX is likely to form. In this compound, A forms the A+ cation, and X forms the X anion. Be sure to justify your answer. Reaction: A(g)+12X2(g)AX(s)The first ionization energy of A(g) is 400 kJ/mol. The electron affinity of X(g) is 525 kJ/mol. The lattice energy of AX(s) is 100 kJ/mol. f If you predicted that no ionic compound would form from the reaction in Part e, what minimum amount of AX(s) lattice energy might lead to compound formation?arrow_forward
- Answer the questions based on the resonance structures of S2O32– (thiosulfate) below. See attatched photo for more information. Draw an “X” through the resonance structure that is not chemically possible. On the remaining three resonance structures, write in any non-zero formal charges. Of the remaining three structures, circle the structure that will contribute the least to the resonance hybrid. Draw a resonance hybrid (including partial “δ” and full charges) for S2O32–.arrow_forwardConsider the anion PF52-. Draw the correct 3-D Lewis Structure. Include all resonance hybrids, if needed. If you use formal charge to determine the best structure, show your calculations. Label (with a value) the F-P-F bond angle(s). Label partial charges on atoms and polar bond vectors, if appropriate. Record the Electron Cloud Geometry and the Molecular Geometry. If the molecule/polyatomic ion has overall molecular polarity, clearly label the overall partial charges and overall molecular polarity vector on the Lewis structure.arrow_forwardWhat possible error(s) exist in the Lewis structure (assume we are trying to represent the best possible Lewis structure for the NO₂S ion knowing N is the central atom in this polyatomic ion)? [:ö==S: N= CO :O: The best structure would have double bond and two lone pairs on each oxygen atom and a single bond with three lone pairs on the sulfur. There are no errors. This is the best possible structure. The Lewis structure above does not minimize formal charges, thus is the not the best possible structure. The nitrogen atom has an expanded octet, and this structure is impossible. The Lewis structure contains the wrong number of electrons, thus this structure is impossible.arrow_forward
- 10.) The structural formula of a certain aldehyde (related to formaldehyde) is H3C-CH2-CHO. Draw a Lewis structure for this aldehyde and determine the number of bonds present. Note that a single or a double or a triple bond counts as one bond. Write the number, not the word.arrow_forwardDraw the best Lewis dot structure for HNO₃, be sure to give the electronic geometry, molecular geometry, bybridization of the central element, polarity, and bond angle around the central element.arrow_forwardAn incomplete Lewis structure is shown below. The structure only shows the atoms and how they are connected. The molecule has a net charge of +1. H H N H Complete the Lewis structure giving all atoms full octets. If there is more than one way to do this, draw resonance structures showing all possibilities. If not, just draw one Lewis structure. Be sure to write in any non-zero formal charges. Click and drag to start drawing a structure. olo Ar 6arrow_forward
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