Chemistry: Principles and Practice
3rd Edition
ISBN: 9780534420123
Author: Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 10, Problem 10.114QE
Formamide, HC(O)NH2, is prepared at high pressures from carbon monoxide and ammonia, and serves as an industrial solvent (the parentheses around the O indicate that it is bonded only to the carbon atom and that the carbon atom is also bonded to the H and the N atoms). Two resonance forms (one with formal charges) can be written for formamide. Write both resonance structures, and predict the bond angles about the carbon and nitrogen atoms for each resonance form. Are they the same? Describe how the experimental determination of the H–N–H bond angle could be used to indicate which resonance form is more important.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Although carbon has four bonds in stable molecules, sometimes reactive carbon intermediates that contain carbon atoms without four bonds are formed for very short time periods. Examples of these unstable intermediates include the methyl carbocation (CH 3) + and the methyl carbanion (CH 3) −. Draw Lewis structures for both unstable ions and predict the shape around carbon.
The structural formulas for ethanol, CH3CH2OH, and propene,
CH;CH=CH,2, are
нн
H
Н—С—С—0—н
H-C-C=C-H
нн
H H H
Ethanol
Propene
(a) Complete the Lewis structure for each molecule showing all valence
electrons.
(b) Using the VSEPR model, predict all bond angles in each molecule.
In the following compounds, the C atoms form a single ring.Draw a Lewis structure for each compound, identify cases for which resonance exists, and determine the carbon-carbon bondorder(s): (a) C₃H₄; (b) C₃H₆; (c) C₄H₆; (d) C₄H₄; (e) C₆H₆.
Chapter 10 Solutions
Chemistry: Principles and Practice
Ch. 10 - Prob. 10.1QECh. 10 - Prob. 10.2QECh. 10 - Prob. 10.3QECh. 10 - Prob. 10.4QECh. 10 - Prob. 10.5QECh. 10 - Prob. 10.6QECh. 10 - Prob. 10.7QECh. 10 - Prob. 10.8QECh. 10 - Prob. 10.9QECh. 10 - Prob. 10.10QE
Ch. 10 - Which atomic orbitals overlap to form the bonds in...Ch. 10 - Prob. 10.12QECh. 10 - Identify the hybrid orbitals used by boron in BCl3...Ch. 10 - Identify the hybrid orbitals used by antimony in...Ch. 10 - Prob. 10.15QECh. 10 - Prob. 10.16QECh. 10 - Prob. 10.17QECh. 10 - Prob. 10.18QECh. 10 - Prob. 10.19QECh. 10 - Prob. 10.20QECh. 10 - Compare and contrast the molecular orbital and...Ch. 10 - Describe the bonding in molecular orbital terms...Ch. 10 - Prob. 10.23QECh. 10 - Prob. 10.24QECh. 10 - Prob. 10.25QECh. 10 - Prob. 10.26QECh. 10 - Prob. 10.27QECh. 10 - Prob. 10.28QECh. 10 - Prob. 10.29QECh. 10 - Prob. 10.30QECh. 10 - Prob. 10.31QECh. 10 - Prob. 10.32QECh. 10 - Prob. 10.33QECh. 10 - Prob. 10.34QECh. 10 - Prob. 10.35QECh. 10 - Prob. 10.36QECh. 10 - Prob. 10.37QECh. 10 - Prob. 10.38QECh. 10 - Prob. 10.39QECh. 10 - Use the VSEPR model to predict the bond angles...Ch. 10 - Prob. 10.41QECh. 10 - Prob. 10.42QECh. 10 - For each of the following molecules, complete the...Ch. 10 - Prob. 10.44QECh. 10 - Prob. 10.45QECh. 10 - Prob. 10.46QECh. 10 - Indicate which molecules are polar and which are...Ch. 10 - Prob. 10.48QECh. 10 - Indicate which of the following molecules are...Ch. 10 - Prob. 10.50QECh. 10 - Prob. 10.51QECh. 10 - Prob. 10.52QECh. 10 - Prob. 10.53QECh. 10 - Prob. 10.54QECh. 10 - Prob. 10.55QECh. 10 - Prob. 10.56QECh. 10 - Prob. 10.57QECh. 10 - Prob. 10.58QECh. 10 - Prob. 10.59QECh. 10 - Prob. 10.60QECh. 10 - Prob. 10.61QECh. 10 - Prob. 10.62QECh. 10 - Prob. 10.63QECh. 10 - Prob. 10.64QECh. 10 - Prob. 10.65QECh. 10 - Prob. 10.66QECh. 10 - Prob. 10.67QECh. 10 - Prob. 10.68QECh. 10 - Prob. 10.69QECh. 10 - Prob. 10.70QECh. 10 - Prob. 10.71QECh. 10 - Prob. 10.72QECh. 10 - Identify the orbitals on each of the atoms that...Ch. 10 - Prob. 10.74QECh. 10 - Prob. 10.75QECh. 10 - How many sigma bonds and how many pi bonds are...Ch. 10 - Give the hybridization of each central atom in the...Ch. 10 - Prob. 10.78QECh. 10 - Prob. 10.79QECh. 10 - Prob. 10.80QECh. 10 - Prob. 10.81QECh. 10 - Predict the hybridization at each central atom in...Ch. 10 - Prob. 10.83QECh. 10 - Tetrafluoroethylene, C2F4, is used to produce...Ch. 10 - Prob. 10.85QECh. 10 - Prob. 10.86QECh. 10 - Prob. 10.87QECh. 10 - Prob. 10.88QECh. 10 - Prob. 10.89QECh. 10 - Prob. 10.90QECh. 10 - Prob. 10.91QECh. 10 - Prob. 10.92QECh. 10 - Prob. 10.93QECh. 10 - Prob. 10.94QECh. 10 - Prob. 10.95QECh. 10 - Prob. 10.96QECh. 10 - Prob. 10.97QECh. 10 - Prob. 10.98QECh. 10 - The molecular orbital diagram of NO shown in...Ch. 10 - The molecular orbital diagram of NO shown in...Ch. 10 - The molecular orbital diagram of NO shown in...Ch. 10 - Prob. 10.102QECh. 10 - Prob. 10.103QECh. 10 - Prob. 10.104QECh. 10 - Prob. 10.105QECh. 10 - Following are the structures of three isomers of...Ch. 10 - The ions ClF2 and ClF2+ have both been observed....Ch. 10 - Aspirin, or acetylsalicylic acid, has the formula...Ch. 10 - Aspartame is a compound that is 200 times sweeter...Ch. 10 - Prob. 10.110QECh. 10 - Prob. 10.111QECh. 10 - Calcium cyanamide, CaNCN, is used both to kill...Ch. 10 - Histidine is an essential amino acid that the body...Ch. 10 - Formamide, HC(O)NH2, is prepared at high pressures...Ch. 10 - Prob. 10.115QECh. 10 - Prob. 10.116QECh. 10 - Prob. 10.117QECh. 10 - Prob. 10.118QECh. 10 - Prob. 10.119QECh. 10 - Prob. 10.120QECh. 10 - Prob. 10.121QECh. 10 - Prob. 10.122QECh. 10 - Prob. 10.123QECh. 10 - Prob. 10.124QECh. 10 - Two compounds have the formula S2F2. Disulfur...Ch. 10 - Prob. 10.126QECh. 10 - Prob. 10.127QE
Knowledge Booster
Learn more about
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_forwardDraw all the equivalent resonance structures for BrO 3¯ on a piece of paper and then fill in the blanks. Draw the structure in such a way that the formal charge on the central atom is zero. Molecular geometry: Number of equivalent resonance structures: Bond order of Br-O bond(s): (fractions rounded to 2 decimal places, e.g. 1/2 will be 0.50 , 4/3 will be 1.33 and 5/3 will be 1.67) Formal charge on terminal atoms participating in resonancearrow_forwardThe carbonate anion, CO32- , is a resonance hybrid. Draw all of the important resonance structures for this molecule. If an atom has a nonzero formal charge, be sure the formal charge is shown clearly in the structure. Use the resonance structures to calculate the average formal charge on each O atom (which are all equivalent in the "true" structure). [Note: all of the important contributing resonance structures have octets around each atom that desires an octet.]arrow_forward
- Oxalic acid (H₂C₂O4) has the following structure: ·o·•·o·• 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. Click and drag to start drawing a structure. с с X 5 c+arrow_forwardUse the following table of bond energies to calculate the enthalpy of combustion (in kJ) of acetylene (C¿H2) gas in oxygen, based on the following chemical equation: C2H2(g) + 2.502(g) → 2CO2(g) + H;O(g) Single Bond H с N H 432 C 411 346 N 386 305 167 459 358 201 142 C=C 602 C=O 799 C=C 835 C=O 1072 Multiple kJ 1 2 3 4 5 6 C 7 8 +/- x 100 Tap here or pull up for additional resources LOarrow_forwardDoes your molecular exhibit resonance? If so, show all possible forms. Does your molecule have any isomers? If so, show Lewis structures of them as well. for CH3CH2OHarrow_forward
- Use the following table of bond energies to calculate the enthalpy of combustion (in kJ) of acetylene (C₂H₂) gas in oxygen, based on the following chemical equation: C₂H₂(g) + 2.5O₂(g) → 2CO₂(g) + H₂O(g)arrow_forwardThe cyanate ion is an anion consisting of one oxygen atom, one carbon atom, and onenitrogen atom, [OCN], in that order. a) Write three (3) resonance contributing structures for the cyanate ion. Show formalcharges.b) Based on your contributing structures, predict the O-C-N bond angle.arrow_forward2) Using bond energies, verify that the complete combustion of ethene gas, C2 H4 (g) (H2C = CH2), to gaseous carbon dioxide and the water is an exothermic reaction.arrow_forward
- (a) Determine the formal charge of oxygen in the following structure. If the atom is formally neutral, indicate a charge of zero. (b) Draw an alternative Lewis (resonance) structure for the compound given in part (a). Show the unshared pairs and nonzero formal charges in your structure. Don't use radicals. Formal charge on O 0arrow_forwardMustard and horseradish are known for their strong taste and smell. The chemical compounds that impart these properties are called isothiocyanates. The simplest isothiocyanate is methyl isothiocyanate, CH3NCS. Draw the Lewis structure of CH3NCS by completing the three resonance forms below. Assign non-zero formal charges and add lone pair electrons. Do not include resonance arrows or additional structures.arrow_forwardCarbon, nitrogen, and oxygen form two different polyatomic ions: cyanate ion (NCO) and fulminate ion (CNO). Write Lewis structures for each anion, including near-equivalent resonance structures (do not add any arrows between structures) and indicating formal charges. The isocyanate ion also has two near-equivalent structures, but the formal charge on the nitrogen attom cannot be reduced to zero: Cyanate ion (NCO)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage LearningChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningChemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Stoichiometry - Chemistry for Massive Creatures: Crash Course Chemistry #6; Author: Crash Course;https://www.youtube.com/watch?v=UL1jmJaUkaQ;License: Standard YouTube License, CC-BY
Bonding (Ionic, Covalent & Metallic) - GCSE Chemistry; Author: Science Shorts;https://www.youtube.com/watch?v=p9MA6Od-zBA;License: Standard YouTube License, CC-BY
General Chemistry 1A. Lecture 12. Two Theories of Bonding.; Author: UCI Open;https://www.youtube.com/watch?v=dLTlL9Z1bh0;License: CC-BY