Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 17, Problem 20P
Interpretation Introduction
Interpretation:
The factors that account for the greater acidity of amides in comparison to
Concept introduction:
The strength of acid of acyl group depends on delocalization of negative charge by electron withdrawing effect. More is the delocalization of charge in the conjugate base, more stable is the anion and thus, stronger is the acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is
formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the
structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it
is dispensed under strict controls because it also causes birth defects.
PPha
NaOCH,CH3
HO-
isotretinoin
HO
A
Br
X
Y
Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.
Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Practice Problem 17.1 Give an IUPAC systematic...Ch. 17 - Prob. 2PPCh. 17 - Practice Problem 17.3 Write structural formulas...Ch. 17 - Practice Problem 17.4
Show how each of the...Ch. 17 - Practice Problem 17.5
Show how you could prepare...Ch. 17 - Practice Problem 17.6
(a) Which of the carboxylic...Ch. 17 - Prob. 7PPCh. 17 - Prob. 8PPCh. 17 - Practice Problem 17.9
Esters can also be...Ch. 17 - Prob. 10PP
Ch. 17 - Prob. 11PPCh. 17 - Practice Problem 17.12
What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 14PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 17PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 19PCh. 17 - Prob. 20PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 22PCh. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 30PCh. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 46PCh. 17 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - Prob. 51PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- NaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forwardCompounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes.arrow_forward19-33 Rank the amines in each set in order of increasing basicity. (b) sbims ne (a) NH2 NH2 N. H (c) H (d) NH2 NH2 NH2 H3C H2 (е) NH2 CH,NH, CONH,arrow_forward
- Amphetamine is a powerful stimulant of the central nervous system.Draw the products formed (and show the flow of electrons) from the acid-base reaction of amphetamine with (a) HCl and with (b) NaH.arrow_forwardAcid-Base Equilibria Many factors contribute to the acidity of organic compounds. Electronegativity, resonance, induction, hybridization, aromaticity, and atomic size, all play a role. In the following comparisons, you are asked to identify the factor(s) that would be most important to analyze when predicting relative acidity, and then to predict the trend in acidity and pKa values. For each of the following pairs of compounds answer the following two multiple-choice questions. 1. What factor(s) are the most important to consider when predicting the relative acidity of the two compounds? a. Electronegativity of the atom possessing the hydrogen. b. Resonance stabilization of the anionic conjugate base. c. Inductive stabilization of the anionic conjugate base. d. Hybridization of the atom possessing the hydrogen. e. The atomic size of the atom possessing the hydrogen.arrow_forward8 (Chemical Connections 19C) Once it has been opened, and particularly if it has been left open to the air, a bottle of aspirin may develop a vinegar-like odor. Explain how this might happen.arrow_forward
- 18-31 Formic acid is one of the components responsible for the sting of biting ants and is injected under the skin by bee and wasp stings. The pain can be relieved by rubbing the area of the sting with a paste of baking soda (NaHCO3) and water, which neutralizes the acid. Write an equation for this reaction.arrow_forwardLow-molecular-weight dicarboxylic acids normally exhibit two different pKa values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one pK unit. Why do the two pKa values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning