Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 20.5, Problem 20.5P
Phenols are less
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The pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that
The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol
The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol
The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol
Both acids are bases
Synthetize 3-phenyl-2-propenoic acid from benzaldehyde using whatever
organic/inorganic reagents are needed.
3-phenyl-2-propenoic = 3-phenylacrylic acid
Propose a method to separate a mixture containing phenol, benzoic acid, naphthalene, and p-nitroaniline. Phenol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. Benzoic acid is soluble in either sodium hydroxide or sodium bicarbonate solutions. Write out the structures of the molecules in your scheme.
Chapter 20 Solutions
Organic Chemistry (9th Edition)
Ch. 20.2C - Prob. 20.1PCh. 20.2C - Name the following carboxylic acids (when...Ch. 20.4B - Rank the compounds in each set in order of...Ch. 20.5 - Prob. 20.4PCh. 20.5 - Phenols are less acidic than carboxylic acids,...Ch. 20.5 - Prob. 20.6PCh. 20.7A - Prob. 20.7PCh. 20.7B - Prob. 20.8PCh. 20.7D - Draw all four resonance forms of the fragment at...Ch. 20.7D - a. Why do most long-chain fatty acids show a large...
Ch. 20.10 - Prob. 20.13PCh. 20.10 - A carboxylic acid has two oxygen atoms, each with...Ch. 20.10 - Prob. 20.15PCh. 20.10 - The mechanism of the Fischer esterification was...Ch. 20.10 - Prob. 20.17PCh. 20.12 - Show how to synthesize the following compounds,...Ch. 20.13 - Show how you would synthesize the following...Ch. 20.14 - Prob. 20.20PCh. 20.14 - Prob. 20.21PCh. 20.15 - Propose a mechanism for the reaction of benzoic...Ch. 20.15 - Prob. 20.23PCh. 20.15 - Prob. 20.24PCh. 20 - Prob. 20.25SPCh. 20 - Give both IUPAC names and common names for the...Ch. 20 - Draw the structures of the following compounds. a....Ch. 20 - Prob. 20.28SPCh. 20 - Arrange each group of compounds in order of...Ch. 20 - Predict the products (if any) of the following...Ch. 20 - Rank the following isomers in order of increasing...Ch. 20 - Prob. 20.32SPCh. 20 - What do the following pKa values tell you about...Ch. 20 - Given the structure of ascorbic acid (vitamin C):...Ch. 20 - Prob. 20.35SPCh. 20 - Show how you would accomplish the following...Ch. 20 - Predict the products and propose mechanisms for...Ch. 20 - Prob. 20.38SPCh. 20 - Prob. 20.39SPCh. 20 - Prob. 20.40SPCh. 20 - Prob. 20.44SPCh. 20 - Prob. 20.45SPCh. 20 - Predict the major form of each compound when it is...
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- In biochemical reactions, decarboxylation of carboxylic acids typically takes place for-keto carboxylic acids. Justify a rational why nature opted for-keto carboxylic acid decarboxylation. Among the following types of biochemical reactions, ester hydrolysis, rearrangement reactions, water elimination reactions, and anhydride hydrolyses, which one is the most favorable one. Rank the above reactions types in the order of being the most to least favorable reactionarrow_forward1. Arrange the test samples in order of increasing reactivity with sodium bicarbonate? Explain briefly -Ethanoic acid, Butanoic acid, Benzoic acid 2. Arrange the test samples in order of increasing solubility in water? Explain briefly. -Ethylamine, Diethylamine, Aniline 3. Arrange the test samples in order of increasing basicity? Explain briefly. -NaOH, Ethylamine, Anilinearrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forward
- Why are carboxylic acids more acidic than alcohols? The increased inductive effect of the alkyl group of the carboxylic acid resonance stabilization of the carboxylate ion (conjugate base of carboxylic acids) Due to hydrogen bonding They have high pKa valuesarrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forward
- Several diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be prepared from acrylonitrile.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_forwardAccount for the fact that one carboxyl group is a considerably stronger acid than the other carboxyl group.arrow_forward
- Provide the reagents necessary to complete the following reactions. More than one step may be necessary, if so number separate steps.arrow_forwardShow how to convert carboxylic acids to other functional groups, and devisemultistep syntheses using carboxylic acids as starting materials and intermediates.Explain how acid chlorides are used as activated derivatives of carboxylic acidsarrow_forwardFollowing are structural formulas for phenol and cyclohexanol along with the acid dis- sociation constants for each. OH НО Cyclohexanol pK, 18 Phenol pK, 9.96 Propose an explanation for the fact that phenol is a considerably stronger acid than cyclohexanol.arrow_forward
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