ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
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 solution
Students have asked these similar questions
In the empty box, provide appropriate reagents and reaction conditions
necessary to convert Salicylic Acid to Aspirin.
HO
2
OH
Salicylic Acid
OH
Aspirin
What is the role of sulfuric acid in the reaction?
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.
Chapter 19 Solutions
ORGANIC CHEMISTRY
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
- After separating the acidic and neutral compounds in a mixture, how does one recover the neutral compound from the organic solution that it is in? O 1) Treat with HCl until acidic to precipitate the neutral compound as a solid. Heat the solution on a hot plate to evaporate the organic solvent and recover O 2) the neutral compound as a solid. Wave a magic wand and speak the spell of recovery to get the neutral O 3) compound as a solid. You don't need to recover the neutral compound as a soild, toss out the O4) organic solution and clean up the lab.arrow_forwardComplete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right.arrow_forward11.27: Tell which is the stronger base and why? Aniline or p-cyanoaniline b) aniline or diphenylamine WH₂ |ال 11.30: Place the following substances, which have nearly identical formula weights, in order of increasing boiling point? 1-aminobutane, 1-butanol, methyl propyl ether, pentanearrow_forward
- What reaction occurs as a hydrochloric acid solution is added to a solution containing equal concentrations of acetic acid and sodium acetate? CH3COOH + H+ → CH3COOH2+ 2CH3COO– + 2H+ → CH3COO + H2 CH3COO– + H+ → CH3COOH CH3COOH + H+ → CH3CO+ + H2O CH3COOH + HCl → CH3COO– + H2Clarrow_forwardEsters Many naturally occurring esters are responsible for the pleasant, characteristic smells of various fruits. As a result, synthetic esters are commonly made for use in perfumes and artificial flavours. To produce a synthetic ester with a specific smell, chemists research what ester will give them the specific smell they are interested in and then they work "backwards" to design a chemical reaction pathway to produce the desired ester using commonly available chemicals. Esters are commonly produced by reacting a carboxylic acid with an alcohol, if the required carboxylic acid and alcohol are not commonly available, chemists have to use a multi-step chemical reaction pathway to first produce the carboxylic acid and/or alcohol, and then produce the desired ester. 1. Show the condensation reactions between the following carboxylic acids and alcohols using the structural formulas of the reactants and products. Name the final ester product. *draw your structures so the functional groups…arrow_forwardThe Brønsted-Lowry definition of acids and bases is: Acids are proton donors, bases are proton acceptors Acids are nucleophiles and bases are electrophiles Acids are proton acceptors, bases are proton donors Carboxy groups are acids and amine groups are bases Carboxy groups are electrophiles and amine groups are nucelophilesarrow_forward
- The esterification reaction of 1 mL each of 1-propanol and propanoic acid is catalyzed with 2-3 drops of sulfuric acid, which is then placed in a test tube in a hot-water bath. After 15 or more minutes, ice water was added. Propyl propanoate is formed. Write the complete equation for the reaction and describe the odor or 1-propanol, propanoic acid, and propyl propanoate.arrow_forwardAll are true or false A) Both LiAlH 4 and NaBH 4 are reducing agents. True or False: Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is less than the polarity of the Al-H bond, so LiAlH 4 is the weaker reducing agent. B) Both Ketones are more sterically hindered and Ketones are less electron deficient due to donation from the two alkyl groups C)Organometallic reagents are strong acids that readily donate a proton to water. D)Organometallic reagents contain a carbon atom bonded to a metal. E) The purpose of a silyl ether to protect alcohols from organometallic reagents and other reagents.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
- 16-35 (Chemical Connections 16B ) What is an alkaloid? Are all alkaloids basic to litmus?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_forwardWill acetylene react with sodium hydride according to the following equation to form a salt and hydrogen, H2? Using pKa values given in Table 4.1, calculate Keq for this equilibrium.arrow_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 Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
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
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co