Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 17, Problem 50P
Number the following compounds in order of increasing pKa value. (Number the most acidic compound 1.)
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Arrange the compounds in each set in order of increasing acid strength. consult Table 4.1 for pKa values of each acid.
Place the following compounds in order of relative acidity. Consider 1 to be the most acidic and 6 to be the least acidic.
Number the following compounds in order of increasing pKa value. (Number the most acidic compound 1.)
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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- 2. Which carboxylic compound of each pair would you expect to be stronger acid? Indicate (a) or (b) on the box provided. (2 pts.) i. (a) (b) OH OH or Me,Ń i. (a) (b) OH (ii) OH or CF3arrow_forwardIdentify the most and the least basic compound in each of the following sets. Leave the remaining answer in each set blank. a) Lithium ethoxide: v Lithium diisopropylamide: v Lithium acetate: b) Sodium chloride: v Sodium formate: Sodium acetate: c) Sodium acetylide: v Sodium p-nitrobenzoate: Sodium benzoate:arrow_forwardIdentify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:arrow_forward
- Rank the molecules in decreasing (strongest to weakest) acidity. Include ALL resonance structures with arrows and explain reasoning for rank.arrow_forwardRank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and in the space provided use resonance (of the conjugate base) to explain why the compound you have labelled “3” is the most acidic.arrow_forwardLabel the most acidic hydrogen in each molecule and justify your choice by using appropriate pKa valuesarrow_forward
- The pka for 2-hydroxybenzoic acid (i.e. salicylic acid, used in pain relief and a precursor for aspirin) is 2.98, while the pKa for 3-hydroxybenzoic acid (found in castoreum, a scent- marking substance secreted by beavers) is 4.08. What does this difference in pK₂ tell us about the relative acidities of these two compounds?, Why is there such a significant difference? OH OH 2-hydroxybenzoic acid (pKa = 2.98) OH OH 3-hydroxybenzoic acid (pKa 4.08)arrow_forwardIdentify the most and the least basic compound in each of the following sets. Leave the remaining answer in each set blank. a) Lithium ethoxide: b) Sodium chloride: c) Sodium acetate: Lithium diisopropylamide: Sodium formate: Sodium methoxide: Lithium acetate: Sodium acetate: Sodium phenoxide:arrow_forward2. Answer ALL parts a) i. 11. NH₂ C NH₂ NH₂ Br E n NH₂ F Rank the compounds shown above in order of INCREASING basicity (least to most basic). Account for the differences in basicity.arrow_forward
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