Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17.15, Problem 32P
Write the mechanism for the reaction of a 1,7-diester with an alkoxide ion to form a cyclic β-keto ester.
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Chapter 17 Solutions
Organic Chemistry (8th Edition)
Ch. 17.1 - Prob. 1PCh. 17.1 - Prob. 2PCh. 17.1 - Prob. 3PCh. 17.1 - Prob. 4PCh. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8PCh. 17.4 - Prob. 9PCh. 17.4 - Prob. 10P
Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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- Part 1. Aqueous 0.010M AgNO 3 is slowly added to a 50-ml solution containing both carbonate [co32-] = 0.105 M and sulfate [soy] = 0.164 M anions. Given the ksp of Ag2CO3 and Ag₂ soy below. Answer the ff: Ag₂ CO3 = 2 Ag+ caq) + co} (aq) ksp = 8.10 × 10-12 Ag₂SO4 = 2Ag+(aq) + soy² (aq) ksp = 1.20 × 10-5 a) which salt will precipitate first? (b) What % of the first anion precipitated will remain in the solution. by the time the second anion starts to precipitate? (c) What is the effect of low pH (more acidic) condition on the separate of the carbonate and sulfate anions via silver precipitation? What is the effect of high pH (more basic)? Provide appropriate explanation per answerarrow_forwardPart 4. Butanoic acid (ka= 1.52× 10-5) has a partition coefficient of 3.0 (favors benzene) when distributed bet. water and benzene. What is the formal concentration of butanoic acid in each phase when 0.10M aqueous butanoic acid is extracted w❘ 25 mL of benzene 100 mL of a) at pit 5.00 b) at pH 9.00arrow_forwardCalculate activation energy (Ea) from the following kinetic data: Temp (oC) Time (s) 23.0 180. 32.1 131 40.0 101 51.8 86.0 Group of answer choices 0.0269 kJ/mole 2610 kJ/mole 27.6 kJ/mole 0.215 kJ/mole 20.8 kJ/molearrow_forward
- Calculate activation energy (Ea) from the following kinetic data: Temp (oC) Time (s) 23.0 180. 32.1 131 40.0 101 51.8 86.0 choices: 0.0269 kJ/mole 2610 kJ/mole 27.6 kJ/mole 0.215 kJ/mole 20.8 kJ/molearrow_forwardCalculate activation energy (Ea) from the following kinetic data: Temp (oC) Time (s) 23.0 180. 32.1 131 40.0 101 51.8 86.0arrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- Rank the compounds in each group below according to their reactivity toward electrophilic aromatic substitution (most reactive = 1; least reactive = 3). Place the number corresponding to the compounds' relative reactivity in the blank below the compound. a. CH₂F CH3 F b. At what position, and on what ring, is bromination of phenyl benzoate expected to occur? Explain your answer. :0: C-O phenyl benzoate 6.Consider the reaction below to answer the following questions. A B C NO₂ FeBr3 + Br₂ D a. The nucleophile in the reaction is: BODADES b. The Lewis acid catalyst in the reaction is: C. This reaction proceeds d. Draw the structure of product D. (faster or slower) than benzene.arrow_forwardPart 2. A solution of 6.00g of substance B in 100.0mL of aqueous solution is in equilibrium, at room temperature, wl a solution of B in diethyl ether (ethoxyethane) containing 25.0 g of B in 50.0 mL 9) what is the distribution coefficient of substance B b) what is the mass of B extracted by shaking 200 ml of an aqueous solution containing 10g of B with call at room temp): i) 100 mL of diethyl ether ii) 50ml of diethyl ether twice iii) 25ml of diethyl ether four timesarrow_forward- Rank the following groups of compounds from most acidic (1) to least acidic (4). Place the number corresponding to the compound's relative rank in the blank below the structure. a. NO₂ NO₂ CH2CH2CH2CH2OH CH3 CH3CH2CHOH CH3CH2CH2CH2OH NO₂ CH3CHCH2CH2OH b. OH OH CH₂OH CO₂H HC CN CN CNarrow_forward
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