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
Videos
Textbook Question
Chapter 3, Problem 16PP
PRACTICE PROBLEM 3.16
Your laboratory instructor gives you a mixture of 4-methylphenol, benzoic acid, and toluene. Assume that you have available common laboratory acids, bases, and solvents and explain how you would proceed to separate this mixture by making use of the solubility differences of its components.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Answer ALL parts of this question.
(a) Using resonance structures, discuss the following statement; phenols are much
stronger acids than aliphatic alcohols.
(b) Give the structure of a stronger organic acid than phenol.
(c) Rationalise the acidity of the latter organic acid by drawing two resonance
structures of the conjugate base.
(d) Eugenol is a natural product derived from the dried flower buds of the evergreen
tree, Eugenia aromatica. Briefly describe a procedure with reagents required to
extract eugenol as a single component from the mixture of compounds present in
these flower buds.
OH
LOCH 3
eugenol
Ethanol, Phenol, picric acid
Arrange them according to the increasing acidity. Explain why and include the drawing of their structure to support your answer.
6. Describe concisely a chemical test to distinguish between the following pairs of
compounds.
Terangkan secara ringkas ujian kimia bagi membezakan pasangan sebatian
berikut.
(a) Propanal and propanone
(b) Phenol and benzoic acid
(c)
Hexan-3-one and hexan-2-one
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
For each IR spectrum below, identify whether it is consistent with the structure of an alcohol, a carboxylic ac...
Organic Chemistry As a Second Language: Second Semester Topics
In qualitative analysis, Ca2+ and Ba2+ are separated from Na+, K+, and Mg2+ by adding aqueous (NH4)2CO3 to a so...
General Chemistry: Atoms First
49. A 25.00-mL sample of an solution of unknown concentration is titrated with a 0.1322 M KOH solution. A volu...
Introductory Chemistry (5th Edition) (Standalone Book)
A 50.0 g piece of iron at 152°C is dropped into 20.0 g H2O(l) at 89 °C in an open, thermally insulated containe...
General Chemistry: Principles and Modern Applications (11th Edition)
Whether the existence of isotopes contradicts part of Dalton’s original atomic theory or not needs to be explai...
Chemistry: Matter and Change
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
General, Organic, and Biological Chemistry: Structures of Life (5th Edition)
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
- Explain the following statements. You must use chemical equations to justify your explanation. (ii) (I) Phenol is more acidic than cyclohexanol.arrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forward6. Describe concisely a chemical test to distinguish between the following pairs of compounds. (a) n-pentanol and 3-methylpentan-3-ol (b) Ethanal dan pentanal (c) Phenol and benzoic acidarrow_forward
- PRACTICE PROBLEM 2.2 The compounds in each part below have the same (or similar) molecular weights. Which compound in cach part would you expect to have the higher boiling point? Explain your answers. (a) OH or (c) OH or HO (b) (CHN or A factor (in addition to polarity and hydrogen bonding) that affects the melting point of many organic compounds is the compactness and rigidity of their individual molecules. • Molecules that are symmetrical generally have abnormally high melting points. sert- Buryl alcohol, for example, has a much higher melting point than the other isomeric alcohols shown here: OH OH tert-Butyl alcohol (mp 25 "C) Butyl alcohol (mp -00 "C) Isobutyl alcohol sec-Butyl alcohol (mp 108 C) (mp-114 C) о оarrow_forward(b) Classify the following alcohols in order of increasing ease of acid-catalyzed dehydration.Justify your answers.arrow_forward(a) Give a seperate chemical test to distinguish between the following pairs of compounds:(i) Ethanol and Phenol (ii) 2-Pentanol and 3-Pentanol(b) Explain Kolbe’s reaction with the help of suitable example.arrow_forward
- 4.3 Explain why each of the following groups is useful in organic synthesis. Use suitable examples and chemical equations to illustrate your answers. (i) (ii) (iii) Benzyl ester group Carboxybenzyl (Cbz) group t-Butyloxycarbonyl (Boc) grouparrow_forward(a) One test for the presence of an alkene is to add a smallamount of bromine, which is a red-brown liquid, and lookfor the disappearance of the red-brown color. This test doesnot work for detecting the presence of an aromatic hydrocarbon.Explain. (b) Write a series of reactions leading topara-bromoethylbenzene, beginning with benzene andusing other reagents as needed. What isomeric side productsmight also be formed?arrow_forwardWrite the equilibrium-constant expressions and obtainnumerical values for each constant in. (a) the basic dissociation of aniline, C6H5NH2. (b) the acidic dissociation of hypochlorous acid,HClO. (c) the acidic dissociation of methyl ammoniumhydrochloride, CH3NH3Cl. (d) the basic dissociation of NaNO2. (e) the dissociation of H3AsO3to H3O+and AsO33-. (f) the reaction of C2O42-with H2O to give H2C2O4and OH-. show solutionarrow_forward
- Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forwardExplain a procedure to separate a mixture of the following 3 compounds to 3 separate individual components. May use any organic solvents and reagents. (Part A is first mixture, Part B is second mixture) First answer (a) then (b)arrow_forwardGive the chemical tests to distinguish between following pair of compounds : (i) Propanol and propanone (ii) Ethyl acetate and methyl acetate (iii) Benzaldehyde and benzoic acid (iv) Benzaldehyde and acetaldehyde (v) Formic acid and acetic acid (vi) Propanal and propanol (vii) Ethanoic acid and ethylethanoatearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY