Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 6.2, Problem 2P
- a. How many σ bond orbitals are available for overlap with the vacant p orbital in the methyl cation?
- b. Which is more stable, a methyl cation or an ethyl cation? Why?
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10. Use the dash-wedge method to draw the 3-D structure of ammonia.
a) What is the name of this type of structure? Trigonal Pyramidel
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Amine
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Let us construct the molecular orbital diagram of ethylene (in pieces). a. First, construct the MO diagram of linear carbene (CH2). Draw pictures of all 6 orbitals b. Now bend the carbene to a bond angle of about 120°. How does this change your MO diagram? Draw pictures of all 6 orbitals. c. Now bring two of these carbene molecules together to make ethylene. Draw pictures of all 12 orbitals.
4. Octatetraene, C8H10, is an 8-membered linear carbon chain with alternating single and double bonds. As a result, each carbon is left with an unhybridized p-orbital containing one electron. This problem will take you through steps to construct and fill the molecular orbital diagram for octatetraene based on the way these different p-orbitals can come together. a) The various molecular orbitals formed from octatetraene’s 8 unhybridized p-orbitals are shown on the next page. Draw the nodal planes for each molecular orbital. Hint: A nodal plane is a line through the molecule that denotes the sites of destructive interference. An example is shown below with ethylene. b) Based on the nodal planes, arrange the energy levels corresponding to the 8 molecular orbitals on the energy level diagram (label them using the numbering provided on the left side of the molecular orbitals) on the next page, in order of lowest to highest energy. c) Populate your molecular…
Chapter 6 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are available for...Ch. 6.2 - Prob. 3PCh. 6.2 - Prob. 4PCh. 6.3 - Prob. 5PCh. 6.3 - Prob. 6PCh. 6.3 - Prob. 7PCh. 6.5 - Prob. 9PCh. 6.5 - Prob. 10PCh. 6.5 - a. What is the major product of each of the...
Ch. 6.5 - Prob. 12PCh. 6.6 - What stereoisomers are obtained from each of the...Ch. 6.6 - Prob. 14PCh. 6.8 - Prob. 15PCh. 6.10 - Name the following:Ch. 6.10 - Draw the structure for each of the following: a....Ch. 6.10 - Draw the structures for and name the seven alkynes...Ch. 6.10 - Name the following:Ch. 6.10 - Name the following:Ch. 6.11 - What hybrid orbitals are used to form the...Ch. 6.13 - Prob. 22PCh. 6.14 - Prob. 23PCh. 6.14 - Which alkyne would be the best one to use for the...Ch. 6.14 - Prob. 25PCh. 6.14 - Prob. 26PCh. 6.15 - Describe the alkyne you would start with and the...Ch. 6.15 - What are products of the following reactions?Ch. 6 - Prob. 29PCh. 6 - Prob. 30PCh. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - What is each compounds systematic name?Ch. 6 - Prob. 34PCh. 6 - Prob. 35PCh. 6 - What reagents could be used to carry out the...Ch. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41PCh. 6 - Prob. 42PCh. 6 - Answer Problem 42 using 2-butyne as the starting...Ch. 6 - What is each compounds systematic name?Ch. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - Prob. 47PCh. 6 - Prob. 48PCh. 6 - Prob. 49PCh. 6 - Prob. 50PCh. 6 - Draw the keto tautomer for each of the following:Ch. 6 - Propose a mechanism for the following reaction...Ch. 6 - Prob. 53PCh. 6 - Prob. 54PCh. 6 - Prob. 55PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 57PCh. 6 - Prob. 58PCh. 6 - Prob. 59PCh. 6 - Prob. 60PCh. 6 - Prob. 61PCh. 6 - Prob. 62P
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- Draw the molecular orbital diagram of a linear C-H (i.e. one carbon atom bonded to one hydrogen atom). Draw out the MOs for orbitals containing electrons. 1. Would you expect C-H to behave as a carbocation, carbanion, or radical? 2. Would removal of one electron from C-H to generate C-H+ increase or decrease the bond length between carbon and hydrogen?arrow_forward4. What is the configuration of all double bonds in the following molecule? Forma 1 2 3 4 5 retinol A. 1: Z; 2: Z; 3: Z; 4: Z; 5: Z B. 1: E; 2: Z; 3: Z; 4: Z; 5: Z C. 1: Z; 2: E; 3: E; 4: E; 5: E D. 1: E; 2: E; 3: E; 4: E; 5: E OHarrow_forward2. Provide the following answer using the following compound below. a. Assign the hybridization for each atom, except hydrogen. b. Determine the number of atomic orbitals and Molecular orbitals (AO, MO). c. Draw the atomic orbitals for each atom and their MO d. Draw the energy diagram. e. Assign the HOMO and LUMO in the energy diagram. H H-C-C=C-H :O: Harrow_forward
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- Paclitaxel is an anticancer drug isolated from the bark of the Pacific yew tree. Below is the structure of Paclitaxel. a.How many hydrogen atoms are present on each carbon atom? Answers should be in arabic numbers (e.g. 23) b. How many sp³ hybridize carbon present in Paclitaxel? Answers should be in arabic numbers (e.g. 23) c.How many sp² hybridize carbon present in Paclitaxel? Answers should be in arabic numbers (e.g. 23) d.How many sp hybridize carbon present in Paclitaxel? Answers should be in arabic numbers (e.g. 23)arrow_forwardIsn't the carbon where the charge changes sp3 hybridized? Wouldn't that make them all non-aromatic? Also, do we need to specify E and Z for the double bonds. Thanks.arrow_forwardQ1. Please answer the following questions with respect to this structure. но. a) What is the hybridization of all atoms in the molecule? b) There are two double bonds in the molecule. For each, indicate the correct stereochemistry, by circling E or Z.arrow_forward
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