Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 15, Problem 80P
When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.
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When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following 1H NMR spectrum. Identify the compound.
When a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following1H NMR spectrum. Identify the compound.
Compound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and C
Chapter 15 Solutions
Organic Chemistry (8th Edition)
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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- Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardThe only organic compound obtained when compound Z undergoes the following sequence of reactions gives the 1H NMR spectrum shown.Identify compound Z.arrow_forward
- The only organic compound obtained when compound Z undergoes the following sequence of reactions gives the 1H NMR spectrum shown. Identify compound Z.arrow_forwardA compound with molecular formula C5H10O2 gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the 1H NMR spectrum shown below is formed. Identify the compounds.arrow_forwardFollowing are 1H-NMR spectra for compounds B (C6H12O2) and C (C6H10O). Upon warming in dilute acid, compound B is converted to compound C. Deduce the structural formulas for compounds B and C.arrow_forward
- Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.arrow_forwardPropose a structure for the compound, C4H8O, that has the following 1H NMR spectrumarrow_forwardWhen heated with an acidic solution of sodium dichromate, compound A forms benzoic acid. Identify compound A from its 1H NMR spectrum. Note: The ppm values for the multiplet shown in the inset ranges from 2.8-3.0 ppm and not 1.1-1.3 ppm as shown.arrow_forward
- Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acylchloride was used in the Friedel–Crafts acylation?arrow_forwardA compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by acidification, it forms the product with the 1H NMR spectrum shown below. Identify the starting material and the productarrow_forwardThe treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forward
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