ORGANIC CHEM.(LL)W/STD GDE.+CONNECT PKG
5th Edition
ISBN: 9781260858129
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Question
Chapter 19, Problem 19.55P
Interpretation Introduction
Interpretation: Using the given information, the steps used for the separation of benzoic acid and cyclohexanol by an extraction procedure is to be explained. The compound which is present in each layer at each stage of the process is to be identified.
Concept introduction: The compounds which have different solubility properties can be separated by extraction procedure. In this procedure, one compound must be soluble in aqueous layer and other one dissolve in organic layer.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.
Carboxylic acids are acidic enough to dissolve in both 10% NaOH and NaHCO3. Phenols, ArOH, are weak acids and most phenols will not dissolve in 10% NaHCO3. How would you separate a mixture of a carboxylic acid (RCOOH), an amine (RNH2), a phenol (ArOH) and a hydrocarbon (RH) using chemically active extraction? Draw a flow chart to illustrate your separation. Show each species in the aqueous and organic layers.
If you have an unknown phenol, what pH you need to achieve upon re-acidification with HCl to ensure that your phenol is 99.9% back in its neutral form?Assume a pKa of 10 for your phenol, and remember that the pH needs to be 3 units different from the pKa for 99.9% ionization or neutralization.
pH 5 or lower
pH 7 or lower
pH 13 or lower
pH 2 or lower
Chapter 19 Solutions
ORGANIC CHEM.(LL)W/STD GDE.+CONNECT PKG
Ch. 19 - Prob. 19.1PCh. 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 - Problem 19.6 Rank the following compounds in order...Ch. 19 - Problem 19.7 Explain how you could use IR...Ch. 19 - Prob. 19.8PCh. 19 - Problem 19.9 How many tetrahedral stereogenic...Ch. 19 - Problem 19.10 What alcohol can be oxidized to each...
Ch. 19 - Problem 19.11 Identify A-D in the following...Ch. 19 - Problem 9.12 Draw the cation that results when a...Ch. 19 - Problem 19.13 Draw the products of each acid-base...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 - Problem 19.17 Rank the compounds in each group in...Ch. 19 - Problem 19.18 Rank the compounds in each group in...Ch. 19 - Prob. 19.19PCh. 19 - Problem 19.20 Which of the following pairs of...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. 19.25PCh. 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. 19.28PCh. 19 - 19.29 Give the IUPAC name for each compound.
a....Ch. 19 - 19.30 Draw the structure corresponding to each...Ch. 19 - Prob. 19.31PCh. 19 - 19.32 Rank the following compounds 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 - 19.36 Draw the products of each acid-base...Ch. 19 - 19.37 Which compound in each pair has the lower ?...Ch. 19 - 19.38 Rank the compounds in each group in order of...Ch. 19 - 19.39 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 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - 19.50 Draw all resonance structures of the...Ch. 19 - As we will see in Chapter 23, CH bonds are...Ch. 19 - Prob. 19.52PCh. 19 - The pKa of acetamide (CH3CONH2) is 16. Draw the...Ch. 19 - 19.54 Write out the steps needed to separate...Ch. 19 - Prob. 19.55PCh. 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 - 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 - 19.71 Hydroxy butanedioic acid occurs naturally in...Ch. 19 - 19.72 Although it was initially sold as a rat...
Knowledge Booster
Similar questions
- 17-35 Suppose that you take a bottle of benzaldehyde (a liquid, bp 179°C) from a shelf and find a white solid in the bottom of the bottle. The solid turns litmus red; that is, it is acidic. Yet aldehydes are neutral compounds. How can you explain these observations?arrow_forwardHow would you go about separating a mixture of 1-chloro-4-methylbenze and salicylic acid using extraction? Describe the procedure in detail and identify whether each component of the mixture is acidic, basic, or neutral.arrow_forwardWrite an equation for the acid-base reaction between 2,4-pentanedione and sodium ethoxide and calculate its equilibrium constant, Keq. The pKa of 2,4-pentanedione is 9; that of ethanol is 15.9.arrow_forward
- 18-28 Arrange these compounds in order of increasing acidity: benzoic acid, benzyl alcohol, phenol.arrow_forwardWrite out a chemical equation (draw bond-line structure) for the reaction between p-bromoaniline with hydrochloric acid. Show the mechanism using curved arrows AND identify the acid and base in the reactants.arrow_forward3. If you have an unknown carboxylic acid, what pH you need to achieve upon re-acidification with HCl to ensure that your carboxylic acid is 99.9% back in its charge neutral form?Assume a pKa of 5 for your carboxylic acid, and remember that the pH needs to be 3 units different from the pKa for 99.9% ionization or charge neutralization. pH 7 or lower pH 5 or lower pH 2 or lower pH 13 or lowerarrow_forward
- Fix each molecule in the drawing area below so that it has the structure it would have if it were dissolved in a 0.1 (aq) solution of NaOH 3-hydroxypropanoic acid and 1,3-dihydroxy-2-propanone .arrow_forward3. You are given a mixture of aspirin, phenol, and naphthalene that you need to separate. i) Draw the structures of each, and identify if they are acidic, basic, or neutral compounds. For each compound draw their reaction with the appropriate acidic or basic conditions that will change their solubility and allow them to be separated. ii) What modifications would you have to make to the experimental protocol in order to separate these three compounds? Provide specifics.arrow_forwardWhat is the pKa of benzoic acid? What is the molar concentration of sodium benzoate (conjugate base)? What is the molar concentration of benzoic acid (weak acid)?arrow_forward
- 9,10-Dihydroxyoctadecanoic acidarrow_forwardCould I please have help with number 5: Show the full structure of the salt that forms when triethylamine reacts with hydrochloric acidarrow_forwardComplete this reaction of a carboxylic acid with a strong base.reaction:C_{6}H_{5}COOH +NaOH->C_{6}H_{5} COO^{-}Na^{+} +H_{2}OC6H5COOH+NaOH⟶C6H5COO−Na++H2Oarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: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
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole