Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 51AP
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From benzene and compounds of 4 carbons or less and any reagents you want; synthesize the following compound.
4-pyranone will readily undergo an acid-base reaction.
Identify the reaction conditions that will result in the
formation of an aromatic product. Then, draw the
aromatic resonance product structure.
Include all lone pairs in your structure. Ignore inorganic
byproducts.
H3O+
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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- A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardWhen propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forwardFollowing is the structural formula of the tranquilizer meparfynol (Oblivon). Oblivon HO Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains al- kyne and hydroxyl functional groups.)arrow_forward
- What reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardH NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forwardRecalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing functional group.arrow_forward
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forward17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward
- Select the best answer. Briefly explain the selection. A mechanism is an acceptable explanation.arrow_forwardAlkyne anions react with the carbonyl groups of aldehydes and ketones to form alkynyl alcohols, as illustrated by the following sequence. HCI CH,C=C Na* + H-C-H [CH,C=C-CH,O Na*] H,O → CH,C=C-CH,OH Propose a mechanism for the formation of the bracketed compound, using curved arrows to show the flow of electron pairs in the course of the reaction.arrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R1 ОН 1. НС—с: Na* R2 R1 R2 2. Нзо" HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Si face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. CH3 CHarrow_forward
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