Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 12.19, Problem 21P
Interpretation Introduction
Interpretation:
Orbital energy diagrams for
Concept introduction:
Huckel MOs are determined by constructing Frost’s circle. It is a polygon with appropriate number of sides inscribed in a circle with one of the corners at the bottom. A horizontal line is drawn through the center of the diagram. MOs that lie below this line are bonding MOs; those on the line are nonbonding while those above the line are antibonding MOs.
In an
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7. Which of the following statements regarding the cyclopropenyl anion is correct? and why?a) It is aromatic.b) It is not aromatic.c) It obeys Hückel’s rule.d) It undergoes reactions characteristic of benzene.e) It has a closed shell of 6 pi electrons.
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Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
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- 1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.arrow_forwardHow does ring strain relates to aromaticity?arrow_forward1. Guanine (1) is commonly represented as a non aromatic, partially saturated heterocycle. However, the common structure of guanine is only one of two possible resonance forms, of whom the second one is clearly aromatic. Knowing that the latter is originated by the delocalisation of one of N6 (nitrogen six) lone pair on the ring, would you be able to predict the structure of the aromatic resonance structure of guanine? Guanine 6 N. 'NH 3 R 1 Why cannot N4 delocalise its lone pair on the ring? What about N3? Is its lone pair delocalised on the pyrimido-imidazole ring? Why?arrow_forward
- Why is benzene less reactive than hexane in terms of stability of free radicals?arrow_forwardb) i) Draw the different structural isomers of the 6-membered ring compound [GAAIBNPAS]H6 in which there are alternating Group 13 and 15 elements. ii) The isomers containing both B-N and AI-N bonding are the most stable. Explain why this is the case. ii) How would you expect the structure and reactivity of the heterocycles [GAAIBNPAS]H6 to compare with borazine? iv) While borazine exists as a planar ring compound, the [GAAIBNPAS]H6 ring compounds dimerize. Explain these observations. H -ЕН -E H-E НЕ ЕН E НЕ- ЕН H `E H. H É-H НЕ E = Heteroatom エー山、 w-Iarrow_forwardDefine about Reactions of Dihalocarbenes ?arrow_forward
- 1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forwardExplain why the Diels Alder reaction would have synthetic significance in the production of biologically active compounds.arrow_forwardAn important class of substances in organic chemistry are the aliphatic and aromatic hydrocarbons and theirssubstituted derivatives. In this assignment: Remember to take any isomerism and the VSEPR principles into account A) Study the series of ring structures a – d in the figure above. Fill in the IUPAC names for the rings a - d.Are any of these rings aromatic? Can you say something about what aromaticity means chemically? B) Suggest probable IUPAC names of the following substituted hydrocarbon compounds which areshown in skeletal structure: See image barrow_forward
- Which of the following molecules could be considered aromatic? Assume all of the compounds are planar. ^ N H₂ Cyclopentadiene is especially acidic for a hydrocarbon. Use a diagram to explain why.arrow_forward(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.arrow_forwardAcrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.arrow_forward
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