ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 16.2, Problem 16.3P
- a. Draw the resonance forms of benzene, cyclobutadiene, and cyclooctatetraene, showing all the carbon and hydrogen atoms.
- b. Assuming that these molecules are all planar, show how the p orbitals on the sp2 hybrid carbon atoms form continuous rings of overlapping orbitals above and below the plane of the carbon atoms.
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A. The overlap of atomic orbitals leads to the formation of bonds. Explain what kind and how many orbitals are used to build the hybrid orbitals of a carbon atom in ethylene to give rise to the three sigma bonds. Also, what happens to the orbital(s) not used in the hybridization process?
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20. BONUS: Why can an sp² hybridized carbon not form a double bond?
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draw a diagram for the valence bond theory that shows the hybrid atomic orbitals and/or the atomic orbitals used to form the molecular orbitals that bond carbon and carbon together in H2CCO. (label all orbitals- atomic, hybrid atomic, and molecular). Calculate the carbon to carbon bond order.
Chapter 16 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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- There are two compounds with the molecular formula HN3. One is called hydrogen azide; the other is cyclotriazene. (a) Write the Lewis structure for each compound. (b) Designate the hybridization of each nitrogen in hydrogen azide. (c) What is the hybridization of each nitrogen in cyclotriazene? (d) How many sigma bonds are in hydrogen azide? In cyclotriazene? (e) How many pi bonds are in hydrogen azide? In cyclotriazene? (f) Give approximate values for the N-to-N-to-N bond angles in each molecule.arrow_forwardBenzene has ____ pi molecular orbitals (include bonding and anti-bonding) of which ____ are filled with electrons.arrow_forward1. a) Draw the dominant Lewis structure for the allene molecule (1,2-propyl diene, CH2CCH2 ) and use VSEPR theory to determine the molecule's geometry. In specifying the geometry give all bond angles and specify which nuclei lie in the same plane. b) Propose a hybridization and bonding scheme for the atoms in allene. That is, specify how each of the atoms is hybridized, which atomic orbitals overlap to form bonding molecular orbitals, and the nature (i.e., sigma", pi, etc.) of these molecular orbitals. c) Draw a plausible valence molecular orbital level diagram for allene (include only bonding MOs) based on the results from (b). d) Based on the work from (c) deduce the valence electronic configuration of the ground state of allene. e) Is the molecule planar or nonplanar? Explain your answer Answer subparts c, d, and earrow_forward
- 1. a) Draw the dominant Lewis structure for the allene molecule (1,2-propyl diene, CH2CCH2 ) and use VSEPR theory to determine the molecule's geometry. In specifying the geometry give all bond angles and specify which nuclei lie in the same plane. b) Propose a hybridization and bonding scheme for the atoms in allene. That is, specify how each of the atoms is hybridized, which atomic orbitals overlap to form bonding molecular orbitals, and the nature (i.e., 0", 7f, etc.) of these molecular orbitals. c) Draw a plausible valence molecular orbital level diagram for allene (include only bonding MOs) based on the results from (b). d) Based on the work from (c) deduce the valence electronic configuration of the ground state of allene. e) Is the molecule planar or nonplanar? Explain your answerarrow_forwardDraw the Lewis Structures for the following molecules and give the hybridization for each carbon atom. a) 2-methyl-1-butanol, CH3CH2CH2(CH3)CH2OH b) Ethyl propanoate, CH3CH2CO2CH2CH3 c) Methyl cyanide (aka acetonitrile), CH3CN d) Isopropyl phenyl ether, (CH3)2CHOC6H5 e) N,N-dimethylpentamide, CH3CH2CH2CH2CON(CH3)2arrow_forward9. How many hybrid orbitals does a carbon atom have in an SP3 hybrid state? Draw the shape of the hybrid orbital.arrow_forward
- CH3+ and CH3− are two highly reactive carbon species. a. What is the predicted hybridization and geometry around each carbon atom? b.Two electrostatic potential plots are drawn for these species. Which ion corresponds to which diagram and why?arrow_forward2. Name the following hydrocarbon. Predict the hybridization (sp³, sp2, o sp) in the asteroid carbon. Mention the shape and bond anglearrow_forwardAllenes are molecules that have multiple double bonds in a row. Below are the condensed structure and a figure showing valence-bond theory for the orbital overlap in the simplest allene. H,C=c=CH, 1. Using the condensed structure, indicate the hybridization for each carbon. 2. Using the condensed structure, indicate the molecular geometry for each carbon. 3. How many o bonds are there in this allene? 4. How many n bonds are there in this allene? 5. Draw a 3-D structure for this allene.arrow_forward
- a. What is the molecular shape around the labeled carbon atom?b. What is the hybridization around that same carbon?c. Based on this structure, would you expect this molecule to absorb light in the visible spectrum? Why or why not?arrow_forwardCarbenes (CR2) are neutral compounds with divalent carbon atoms. Propose two different ways that carbenes could exist. Provide the hybridization of each carbene carbon and predict the bond angles based on what you know about hybridizationarrow_forwardThe Lewis structure of an organic compound is shown below. Determine the orbitals used in bonding, as well as the number of sigma and pi bonds. 1サー= 10 H. N: H. 11 Total sigma bonds: [Select] Total pi bonds: [Select ] Write "none" if no orbital of that type is used to bond. Unhybridized orbital used to Hybridized orbital used to Atom bond bond [ Select ] [ Select ] [ Select] [ Select ] C # 2 [ Select ] [ Select ] [ Select ] [ Select]arrow_forward
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