EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 21, Problem 21.12P
Interpretation Introduction
Interpretation:
The reason as to why the acid-catalyzed hydrolysis of esters is faster than that of amides is to be explained using the analysis of resonance effects and leaving-group basicities.
Concept introduction:
The hydrolysis is the reaction in which a compound is broken down using the molecule of water. The hydrolysis reactions are generally catalyzed by acids and bases. The hydrolysis of the carboxylic derivatives produces
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Explain why carboxylic acids do not undergo nucleophilic acyl substitution reactions with amines.
Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
Hydration of aldehydes and ketones can be catalyzed by acid
or base. Bases catalyze hydration by:
protonating the carbonyl oxygen
making the carbonyl group more electrophilic
employing hydroxide ion, which is a better nucleophile than water
making the carbonyl group less electrophilic
shifting the equilibrium position of the reaction to favor products
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
Ch. 21 - Prob. 21.1PCh. 21 - Prob. 21.2PCh. 21 - Prob. 21.3PCh. 21 - Prob. 21.4PCh. 21 - Prob. 21.5PCh. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - Prob. 21.8PCh. 21 - Prob. 21.9PCh. 21 - Prob. 21.10P
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Prob. 21.18PCh. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Prob. 21.22PCh. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Prob. 21.28PCh. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Prob. 21.31PCh. 21 - Prob. 21.32APCh. 21 - Prob. 21.33APCh. 21 - Prob. 21.34APCh. 21 - Prob. 21.35APCh. 21 - Prob. 21.36APCh. 21 - Prob. 21.37APCh. 21 - Prob. 21.38APCh. 21 - Prob. 21.39APCh. 21 - Prob. 21.40APCh. 21 - Prob. 21.41APCh. 21 - Prob. 21.42APCh. 21 - Prob. 21.43APCh. 21 - Prob. 21.44APCh. 21 - Prob. 21.45APCh. 21 - Prob. 21.46APCh. 21 - Prob. 21.47APCh. 21 - Prob. 21.48APCh. 21 - Prob. 21.49APCh. 21 - Prob. 21.50APCh. 21 - Prob. 21.52APCh. 21 - Prob. 21.53APCh. 21 - Prob. 21.54APCh. 21 - Prob. 21.55APCh. 21 - Prob. 21.56APCh. 21 - Prob. 21.57APCh. 21 - Prob. 21.58APCh. 21 - Prob. 21.59APCh. 21 - Prob. 21.60APCh. 21 - Prob. 21.61APCh. 21 - Prob. 21.62APCh. 21 - Prob. 21.63AP
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- Write the mechanism for the following reactions: 1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine 2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?arrow_forwardCarbonyl compounds can be protonated on the carbonyl oxygen. Protonation of the carbonyl oxygen gives a species whose positive charge is delocalized by resonance. Explain why acetic acid (ethanoic acid) is more readily protonated than acetone (propanone).arrow_forwardCarboxylic Acid Derivatives Resolve the reactions.arrow_forward
- explain why an N,N-disubstituted amide is less acidic than an ester.arrow_forwardRänk the carboxylic acids in order of increasing acidity.arrow_forwardWhy does a substance become more soluble in a solvent with increasing temperature? Solvents are ordered by decreasing value of theirdielectric constant. In the table, which is the most polar solvent and which is the least polar? How can acetylsalicylic acid be obtained from salicylic acid?arrow_forward
- Why are carbonyl compounds considered weakly acidic? Would you expect carbonyl compounds to be more acidic than alkanes? Explain.arrow_forwardRank these compounds in order of decreasing acidity.arrow_forwardWhat explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.arrow_forward
- Many multi-step organic reaction mechanisms involve proton transfer steps. For example, the first step of Fischer esterification of carboxylic acids(as shown with acedic acid) is activation of the acid by protonation. Based on your understanding of which reaction pathway is more favorable, explain why using chemical structures.arrow_forwardRank the following in order of decreasing basicity and explain why (based on their structures). hydroxide ion, ethoxide ion, phenoxide ion, and carboxylate ionarrow_forwardBisphenol A is widely used as a building block in polymer synthesis and is found in the polycarbonate hard plastics of reusable drink containers, DVDs, cell phones, and other consumer goods. Bisphenol A is reported to have estrogenic activity, and its widespread occurrence in our environment is a potential concern. Describe one or two biochemical experiments that could be done to compare the activity of bisphenol A with that of its estradiol, its structural relative.arrow_forward
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