Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13, Problem 26P
Interpretation Introduction
Interpretation:
The
Concept introduction:
Acidity of
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The pKa of acetamide (CH3CONH2) is 16. Draw the structure for its conjugate base and explain why acetamide is less acidic than CH3COOH.
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Chapter 13 Solutions
Essential Organic Chemistry, Global Edition
Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2PCh. 13.1 - Prob. 3PCh. 13.1 - Prob. 4PCh. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6PCh. 13.2 - Prob. 7PCh. 13.3 - Prob. 8PCh. 13.3 - Prob. 9PCh. 13.3 - Prob. 10P
Ch. 13.4 - Prob. 11PCh. 13.5 - Prob. 12PCh. 13.5 - Prob. 13PCh. 13.6 - Prob. 14PCh. 13.7 - Prob. 16PCh. 13.8 - Prob. 17PCh. 13.8 - Prob. 18PCh. 13.8 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.10 - Propose a mechanism for the formation of...Ch. 13.10 - Prob. 22PCh. 13.10 - a. If the biosynthesis of palmitic acid were...Ch. 13 - Draw the enol tautomers for each of the following...Ch. 13 - Number the following compounds in order from...Ch. 13 - Prob. 26PCh. 13 - Explain why the pKa of a hydrogen bonded to the...Ch. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Using cyclopentanone as the reactant, show the...Ch. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - Describe how the following compounds can be...Ch. 13 - Prob. 46PCh. 13 - Which would require a higher temperature:...Ch. 13 - Prob. 48PCh. 13 - Propose a mechanism for the following reaction:Ch. 13 - Show how the following compounds could be...Ch. 13 - Prob. 51PCh. 13 - Prob. 52P
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- What is the conjugate acid of acetamide and its pka value?arrow_forwardAliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. Is that true or false?arrow_forwardAlthough it was initially sold as a rat poison, warfarin is an effective anticoagulant used to prevent blood clots. Label the most acidic proton in warfarin, and explain why its pKa is comparable to the pKa of a carboxylic acid.arrow_forward
- Place the binders below in descending order of acidity (pi) and justify your choice: CH3CN; (C2H5)2O; PCl3; As(C6H5)3; (C2H5)3Narrow_forwardAlthough it was initially sold as a rat poison, warfarin is an effectiveanticoagulant used to prevent blood clots. Label the most acidic protonin warfarin, and explain why its pKa is comparable to the pKa of acarboxylic acid.arrow_forwardExplain why a base can remove a proton from the alpha-carbon of N,N-dimethylethanamide but not from the alpha-carbon of either N-methylethanamide or ethanamide.arrow_forward
- Would you expect 2-Chlorobutanoic acid to have higher or lower pka than 4-Chlorobutanoic acid?arrow_forward(1) Which is the most basic amine and which is a secondary amine? (2) Which can undergo hydrolysis? (3) Which gives a diazonium salt upon reaction with HNO2, HCl at 0oC?arrow_forwardEach pair of compounds below can be separatedusing acid/base extraction. Provide the common acid or base that could be used to effect the separation. Amines can be converted into ammonium salts using acid, but neutral amines are very weak acids (pKa~ 35)and thus cannot be extracted by an aqueous base.arrow_forward
- Acetic, formic, hydrofluoric, and acetylsalicylic acids have the following values of pKa (25°C), respectively: 4.74, 3.74, 3.17, 3.49. Order these acids in order acidity (from highest to lowest acidity)arrow_forwardgive the results of the following compounds after reaction with nitrous acid test a. primary aliphatic amine b. secondary aliphatic amine c. tertiary aliphatic amine d. primary aromatic aminearrow_forwardThe side chain of acetyl-L-lysine-OMe has a pKa=10.5 and its acid-dissociation reaction is shown below. B. At what pH does [A-]=[HA]?arrow_forward
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