EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 15, Problem 77P
- a. When a
carboxylic acid is dissolved in isotopically labeled water (H2 18O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
- b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH3 18OH) and an acid catalyst is added, where will the label reside in the product?
- c. If an ester is dissolved in isotopically labeled water (H2 18O) and an acid catalyst is added, where will the label reside in the product?
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a. When a carboxylic acid is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.
b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH318OH) and an acid catalyst is added, where will the label reside in the product?c. If an ester is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, where will the label reside in the product?
6. Show how to synthesize the target molecule from the given material as the only source
of carbon. Show the reagents needed for each step and the product of each step.
OH
.OH
Draw the major product of this reaction. Ignore inorganic
byproducts.
1. Hg(OAc)2, H₂O
2. NaBH4, NaOH
Drawing
at
Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
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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- 4. Both the Markovnikov and anti-Markovnikov hydration of alkynes proceed through an enol intermediate (1 and 2, respectively). Provide a mechanism for the conversion of each enol to its corresponding final product. H₂SO4, H₂O HgSO4 1. Sia₂BH 2. H₂O₂, NaOH [Y] 2 NaOH OH [۴] H₂O+ Larrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts. Assume that the water side product is continuously removed to drive the reaction toward products. CH3NH2, TSOH P Type here to search 五0arrow_forwardIn the mechanism for the acid-catalyzed hydrolysis of an ester, a. what species could be represented by HB+? b. what species could be represented by :B? c. what species is HB+ most likely to be in the hydrolysis reaction? d. what species is HB+ most likely to be in the reverse reaction?arrow_forward
- 4) When a mixture of two different compounds both containing a hydrogens are placed under acidic or basic conditions, crossed aldol products can be formed. By either self-condensation or cross condensations. Draw the 4 aldol and 4 a.B-unsaturated ketones that can be made from the following mixed system. -OH 4 products One way to control this is by either having only one compound with a hydrogens or by reacting the desired nucleophile with lithium diisopropylamide (LDA) before addition of second carbonyl. The issue here is that this reaction stops at the aldol unless excess base is used. он LDA OH heat Show a synthetic scheme of how to use the following carbonyls to control the formation of each cross product (i.e. each as nucleophile and electrophile, two reactions). andarrow_forwardRank the following bases in order from slowest E2 reaction rate to fastest. ONa H20 NaOH NH3 OK ONa A В D E Farrow_forwardWhich best explains the following reaction. O O OH H3O+ This reaction works and the only ether product formed is shown. This reaction does not work because the major product would be an alkene formed by elimination. This reaction does not work because the major product would be an ester. This reaction does not work because three ethers can be formed. OH +arrow_forward
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- For each of the following reactions, predict the major product. H2N HO 1. H2NNH2, acetic acid 2. NaOH, A .CN H20 H2SO4arrow_forward4. Although the compound below has three ester groups, however only one possible Dieckmann product can be formed. Determine the product of the reaction below and draw out the mechanism. EtO EtO OEt 1. NaOEt, EtOH 2. mild H3O+ workup ?arrow_forwardSelect the reagent that you would use to convert an alkene to an epoxide. mCPBA 03, then DMS BH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4arrow_forward
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