Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 1, Problem 1.73AP
Following is a structural formula of benzene, C6H6, which we study in Chapter 21.
- (a) Using VSEPR, predict each H—C—C and C—C—C bond angle in benzene.
- (b) State the hybridization of each carbon in benzene.
- (c) Predict the shape of a benzene molecule.
- (d) Draw important resonance contributing structures.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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.
Draw a Lewis structure for each of the following molecules:
(a) chlorodifluoromethane, CHClF2
(b) propanoic acid, C2 H5CO2H (basic structure pictured below)
(c) acetonitrile, CH3CH (the framework is H3C-C-N)
(d) allene, H3CCCH2
Ethylene, C₂H₄, and tetrafluoroethylene, C₂F₄, are used tomake the polymers polyethylene and polytetrafluoroethylene(Teflon), respectively.(a) Draw the Lewis structures for C₂H₄ and C₂F₄, and give theideal H-C-H and F-C-F bond angles.(b) The actual H-C-H and F-C-F bond angles are 117.4and 112.4, respectively. Explain these deviations.
Chapter 1 Solutions
Organic Chemistry
Ch. 1.1 - Prob. 1.1PCh. 1.2 - Prob. 1.2PCh. 1.2 - Judging from their relative positions in the...Ch. 1.2 - Classify each bond as nonpolar covalent or polar...Ch. 1.2 - Using the symbols and +, indicate the direction...Ch. 1.2 - Draw Lewis structures showing all valence...Ch. 1.2 - Draw Lewis structures for these ions and show...Ch. 1.3 - Draw Lewis structures and condensed structural...Ch. 1.3 - Prob. 1.9PCh. 1.3 - Prob. 1.10P
Ch. 1.3 - Prob. 1.11PCh. 1.3 - Prob. 1.12PCh. 1.4 - Predict all bond angles for these molecules. (a)...Ch. 1.5 - The geometry of carbon in diamond is tetrahedral,...Ch. 1.5 - Because of their spherical shape, C60 molecules...Ch. 1.5 - What best describes the CCC bond angles in C60? 1....Ch. 1.5 - Prob. 1.14PCh. 1.7 - Describe the bonding in these molecules in terms...Ch. 1.8 - Prob. 1.16PCh. 1.8 - Prob. 1.17PCh. 1.8 - Prob. 1.18PCh. 1.9 - Draw three contributing structures of the...Ch. 1.9 - What is the hybridization state of the circled...Ch. 1.9 - The molecule shown on the right in the example in...Ch. 1.9 - Prob. CQCh. 1.9 - The following structure is called imidazolium....Ch. 1 - Write the ground-state electron configuration for...Ch. 1 - Identify the atom that has each ground-state...Ch. 1 - Define valence shell and valence electron.Ch. 1 - How many electrons are in the valence shell of...Ch. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Write Lewis structures for these compounds. Show...Ch. 1 - Write Lewis structures for these ions. Show all...Ch. 1 - Prob. 1.29PCh. 1 - Some of these structural formulas are incorrect...Ch. 1 - Following the rule that each atom of carbon,...Ch. 1 - Following are several Lewis structures showing all...Ch. 1 - Which statements are true about electronegativity?...Ch. 1 - Why does fluorine, the element in the upper right...Ch. 1 - Arrange the single covalent bonds within each set...Ch. 1 - Using the values of electronegativity given in...Ch. 1 - Prob. 1.37PCh. 1 - Use VSEPR to predict bond angles about each...Ch. 1 - Use VSEPR to predict bond angles about each atom...Ch. 1 - Use VSEPR to predict the geometry of these ions....Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - Draw structural formulas for (a) The four primary...Ch. 1 - Draw structural formulas for the three tertiary...Ch. 1 - Prob. 1.47PCh. 1 - Identify the functional groups in each compound.Ch. 1 - Draw a three-dimensional representation for each...Ch. 1 - Tetrafluoroethylene, C2F4, is the starting...Ch. 1 - Which statements are true about resonance...Ch. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Are the structures in each set valid contributing...Ch. 1 - State the orbital hybridization of each...Ch. 1 - Describe each highlighted bond in terms of the...Ch. 1 - Following is a structural formula of the...Ch. 1 - Draw a Lewis structure for methyl isocyanate,...Ch. 1 - What is the hybridization of the highlighted atoms...Ch. 1 - Using cartoon representations, draw a molecular...Ch. 1 - In what kind of orbitals do the lone-pair...Ch. 1 - Draw the delocalized molecular orbitals for the...Ch. 1 - Prob. 1.64APCh. 1 - Each compound contains both ions and covalent...Ch. 1 - Predict whether the carbon-metal bond in these...Ch. 1 - Prob. 1.67APCh. 1 - Phosphorus is immediately under nitrogen in the...Ch. 1 - Draw a Lewis structure for the azide ion, N3. (The...Ch. 1 - Cyanic acid, HOCN, and isocyanic acid, HNCO,...Ch. 1 - In Chapter 6, we study a group of organic cations...Ch. 1 - Many reactions involve a change in hybridization...Ch. 1 - Following is a structural formula of benzene,...Ch. 1 - Following are three contributing structures for...Ch. 1 - (a) Draw a Lewis structure for the ozone molecule,...Ch. 1 - The following two compounds are isomers; that is,...Ch. 1 - In future chapters, we will encounter...Ch. 1 - Prob. 1.78AP
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
- Hydrazine, N₂H₄, and carbon disulfide, CS₂, form a cyclicmolecule(right).(a) Draw Lewisstructures for N₂H₄ and CS₂. (b) How do electron-group arrange-ment, molecular shape, and hy-bridization of N change when N₂H₄ reacts to form the product?(c) How do electron-group arrangement, molecular shape, andhybridization of C change when CS₂ reacts to form the product?arrow_forwardDraw a Lewis structure for each of the following molecule: (a) chlorodifluoromethane, CHCIF2 (b) propanoic acid C2H5CO2H (basic structure pictured below) (c) acetonitrile, CH3CN ( the framework is H3C-C-N) (d) allene, H2CCCH2arrow_forwardConsider the collection of nonmetallic elements O, P, Te,I, and B. (a) Which two would form the most polar singlebond? (b) Which two would form the longest single bond?(c) Which two would be likely to form a compound of formulaXY2? (d) Which combinations of elements would likelyyield a compound of empirical formula X2Y3?arrow_forward
- (a) Complete the Lewis structure for vinyl chloride by showing all unshared pairs of electrons. (b) Predict the H-C-H, H-C-C, and Cl-C-H bond angles in this molecule. (c) Does vinyl chloride have polar bonds? Is it a polar molecule? Does it have a dipole?arrow_forwardTwo important industrial chemicals, ethene, C2H4, and propene, C3H6, are produced by the steam (or thermal) cracking process: 2C3H8(g) ⟶ C2H4(g) + C3H6(g) + CH4(g) + H2(g) For each of the four carbon compounds, do the following: (a) Draw a Lewis structure. (b) Predict the geometry about the carbon atom. (c) Determine the hybridization of each type of carbon atom.arrow_forwardConsider the molecules BF₃, PF₃, BrF₃, SF₄, and SF₆.(a) Which has bonds that are the most polar?(b) Which have a molecular dipole moment?arrow_forward
- Which statements are true about resonance contributing structures? (a) All contributing structures must have the same number of valence electrons. (b) All contributing structures must have the same arrangement of atoms. (c) All atoms in a contributing structure must have complete valence shells. (d) All bond angles in sets of contributing structures must be the same.arrow_forwardChloral (Cl₃C—CH=O) forms a monohydrate, chloralhydrate, the sleep-inducing depressant called “knockout drops”in old movies. (a) Write two possible structures for chloral hy-drate, one involving hydrogen bonding and one that is a Lewis adduct. (b) What spectroscopic method could be used to identify the real structure? Explain.arrow_forwardIdentify the set of covalent bonds that shows the correct trend of increasing bond polarity. (A) H―F < H―Cl < H―Br < H―I; (B) H―C < H―N < H―O < H―F; (C) H―O < H―S < H―Se < H―Te; (D) H―C < H―Si < H―Ge < H―Sn;arrow_forward
- Nitrogen trifluoride (NF3) is used in the electronics industry to clean surfaces. NF3 is also a potent greenhouse gas. (A) Draw the Lewis structure of NF3 and determine its molecular geometry. (B) BF3 and NF3 both have three covalently bonded fluorine atoms around a central atom. Do they have the same dipole moment? (C) Could BF3 also behave as a greenhouse gas? Explain why or why not.arrow_forwardTwo important industrial chemicals, ethene, C2H4, and propene, C3H6, are produced by the steam (or thermal) cracking process:2C3 H8(g) ⟶ C2 H4(g) + C3 H6(g) + CH4(g) + H2(g)For each of the four carbon compounds, do the following:(a) Draw a Lewis structure.(b) Predict the geometry about the carbon atom.(c) Determine the hybridization of each type of carbon atom.arrow_forwardIn addition to ammonia, nitrogen forms three other hy-drides: hydrazine (N₂H₄), diazene (N₂H₂), and tetrazene (N₄H₄).(a) Use Lewis structures to compare the strength, length, and or-der of nitrogen-nitrogen bonds in hydrazine, diazene, and N₂.(b) Tetrazene (atom sequence H₂NNNNH₂) decomposes above 0°C to hydrazine and nitrogen gas. Draw a Lewis structure fortetrazene, and calculate ΔH°ᵣₓₙ for this decomposition.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher: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