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Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 19, Problem 19.49P
Draw all resonance structures of the conjugate bases formed by removal of the labeled protons
a. b.
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Students have asked these similar questions
Phenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the
conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.)
OH
phenol
OH
-H*
- H*
4-hyroxybenzaldehyde
Rank 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.
Identify 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:
Chapter 19 Solutions
Organic Chemistry-Package(Custom)
Ch. 19 - Give the IUPAC name for each compound.Ch. 19 - Problem 19.2 Give the structure corresponding to...Ch. 19 - Problem 19.3 Draw the structure corresponding to...Ch. 19 - Prob. 19.4PCh. 19 - Prob. 19.5PCh. 19 - Rank the following compounds in order of...Ch. 19 - Explain how you could use IR spectroscopy to...Ch. 19 - Identify the structure of a compound of molecular...Ch. 19 - Problem 19.9 How many tetrahedral stereogenic...Ch. 19 - What alcohol can be oxidized to each carboxylic...
Ch. 19 - Prob. 19.11PCh. 19 - Draw the products of each acid-base reaction.Ch. 19 - Problem 19.14 Given the values in Appendix A,...Ch. 19 - Problem 19.15 Rank the labeled protons in...Ch. 19 - Problem 19.16 Match each of the following values ...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - Prob. 19.18PCh. 19 - Which of the following pairs of compounds can be...Ch. 19 - Problem 19.21 Two other commonly used sulfonic...Ch. 19 - Problem 19.22 Draw both enantiomers of each amino...Ch. 19 - Problem 19.23 Explain why amino acids, unlike most...Ch. 19 - Problem 19.24 Draw the positively charged,...Ch. 19 - Prob. 19.24PCh. 19 - Problem 19.26 Explain why the of the group of...Ch. 19 - Answer each question for A and B depicted in the...Ch. 19 - Prob. 19.27PCh. 19 - Give the IUPAC name for each compound. a....Ch. 19 - Prob. 19.29PCh. 19 - Draw the structures and give the IUPAC names for...Ch. 19 - Prob. 19.31PCh. 19 - Rank the compounds in each group in order of...Ch. 19 - 19.33 Draw the organic products formed in each...Ch. 19 - 19.34 Identify the lettered compounds in each...Ch. 19 - 19.35 Using the table in Appendix A, determine...Ch. 19 - Draw the products of each acid-base reaction, and...Ch. 19 - Which compound in each pair has the lower pKa?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - Rank the compounds in each group in order of...Ch. 19 - 19.40 Match the values to the appropriate...Ch. 19 - Prob. 19.41PCh. 19 - 19.42 Which carboxylic acid has the lower ,...Ch. 19 - Prob. 19.43PCh. 19 - 19.44 Explain the following statement. Although...Ch. 19 - Prob. 19.45PCh. 19 - 19.46 Explain why the of compound A is lower than...Ch. 19 - 19.47 Rank the following compounds in order of...Ch. 19 - Explain the following result. Acetic acid...Ch. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.51PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.54PCh. 19 - Can octane and octan -1- ol be separated using an...Ch. 19 - 19.57 Identify each compound from its spectral...Ch. 19 - 19.58 Use the NMR and IR spectra given below to...Ch. 19 - 19.59 An unknown compound (molecular formula )...Ch. 19 - 19.60 Propose a structure for (molecular formula...Ch. 19 - Prob. 19.60PCh. 19 - 19.61 Match the data to the appropriate...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.64PCh. 19 - 19.65 For each amino acid ,draw its neutral,...Ch. 19 - Calculate the isoelectric point for each amino...Ch. 19 - 19.67 Lysine and tryptophan are two amino acids...Ch. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - Prob. 19.70PCh. 19 - Prob. 19.71PCh. 19 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
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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
- Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)arrow_forwardDraw the major organic product of the Bronsted acid-base reaction between the compounds shown below. Include all lone pairs and charges as appropriate. Ignore any counterions. HH 1 eq. base H H H oarrow_forwardRank the indicated a-H’s from most to least acidic (most acidic= 1). Be sure to explain your rankings for each by drawing significant resonance structures for the conjugate base and commenting on any other factors that contribute to your rankings.arrow_forward
- Explain the trends in the acidity of phenol and the monofluoro derivatives of phenol. OH он он он F pк, 10.0 pK, 8.81 pK, 9.28 pK, 9.81arrow_forwardBr NH₂ OH NH₂ CH3 A/RO/exception Circle the more acidic compound and determine the effect responsible for such observation using ARIO methods, or if its an exception to the rule. Please explain thanks.arrow_forward4 5 Arrange the following bases in increasing base strength. There is no partial credit on this problem. Weakest base 1 2 3 Pyridine (C5H5N), Kb = 1.7 x 10-⁹ Aniline (C6H5NH2), Kb = 3.9 x 10-10 Strongest base Methylamine (CH3NH₂), Kb = 4.4 x 10-4 Hydrazine (N2H4), Kb = 1.3 x 10-6 ⠀ Dimethylamine ((CH3)2NH), K₂ = 5.1 x 10-4arrow_forward
- 4-Cyanophenol has a pKa = 8.0, whereas phenol has a pKa= 10.0. Resonance form that best illustrates why 4-cyanophenol is more acidic isarrow_forwardHow is nucleophilicity (nucleophile strength) related to basicity?arrow_forward1. Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do. HF NH3 H2SO4 CH3OH CH3COOH H3O+ H2O2. Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups. CH4 CH3NO2 CH2(NO2)2 CH(NO2)3arrow_forward
- Select the stronger base from each pair of compounds.arrow_forward1. Explain why the protonation of pyrrole occurs at C2 to form A, rather than the N atom to form B 2. Explain why compound A is more acidic than C, the conjugate acid of pyridine. :N-H H H H -H Pyrrole pKa=0.4 pKa=5.3 A B C Harrow_forwardHow would you describe the reaction between NaOH (a base) and the mixture of benzoic acid and methyl benzoate? Both react with NaOH because bases accept protons Neither react with NaOH because neither has an acidic proton Benzoic acid reacts with NaOH because it has an acidic proton, but methylbenzoate does not Methyl benzoate reacts with NaOH because it has an acidic proton, but benzoic acid does notarrow_forward
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