Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 20.5, Problem 20.4P
Interpretation Introduction
Interpretation:
The use of acid-base extractions to purify the heptanoic acid is to be stated and the chart that shows the impurities at each stage is to be given.
Concept introduction:
Acid-base extraction is the technique that is used to separate the acidic and basic substance from the mixture on the basis of their chemical properties. This technique is used during the work up of a reaction after the synthesis of the compounds, so that the product becomes free from any type of impurities. The acidic or basic substances that are similar in chemical properties are impossible to separate through this method.
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20:32
hydroxide
2. Using curved arrows, show the deprotonation mechanism of phenol with
(OH). Also, provide the structure of the product of this deprotonation.
Start answering this question by drawing the structure of phenol. Then
hydroxide ion. Find your most reactive electrons and draw the curved arrow that
shows where they would go to deprotonate phenol. Then "make a bond break a
bond"
write they
question
3. Provide valid resonance structures for the product of
the previous
arrow(s)
charge moving onto the ortho- and para positions. Use curved
to show how the charge resonates to the next structure in your scheme.
all the proper notations for depicting resonance.
that show the
in the structures
Be sure to use
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C
Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic
acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N-
bromosuccinimide, PBR3, SOCI2, AlCl3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium
diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH =
disecondary isobutyl borane, KMNO4, HIO4 = periodic acid
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write the missing reagents and solvents over the arrows. Some transformation require
multiple steps. In some cases there will be multiple arrows.
Br
Br
Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic
acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N-
bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium
diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH =
disecondary isobutyl borane, KMNO4, HIO4 = periodic acid
%3D
%3D
%3D
%3D
%3D
%3D
%3D
write the missing reagents and solvents over the arrows. Some transformation require
multiple steps. In some cases there will be multiple arrows.
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H.
(R)
Br
(S)
HO
OH
Chapter 20 Solutions
Organic Chemistry (9th Edition)
Ch. 20.2C - Prob. 20.1PCh. 20.2C - Name the following carboxylic acids (when...Ch. 20.4B - Rank the compounds in each set in order of...Ch. 20.5 - Prob. 20.4PCh. 20.5 - Phenols are less acidic than carboxylic acids,...Ch. 20.5 - Prob. 20.6PCh. 20.7A - Prob. 20.7PCh. 20.7B - Prob. 20.8PCh. 20.7D - Draw all four resonance forms of the fragment at...Ch. 20.7D - a. Why do most long-chain fatty acids show a large...
Ch. 20.10 - Prob. 20.13PCh. 20.10 - A carboxylic acid has two oxygen atoms, each with...Ch. 20.10 - Prob. 20.15PCh. 20.10 - The mechanism of the Fischer esterification was...Ch. 20.10 - Prob. 20.17PCh. 20.12 - Show how to synthesize the following compounds,...Ch. 20.13 - Show how you would synthesize the following...Ch. 20.14 - Prob. 20.20PCh. 20.14 - Prob. 20.21PCh. 20.15 - Propose a mechanism for the reaction of benzoic...Ch. 20.15 - Prob. 20.23PCh. 20.15 - Prob. 20.24PCh. 20 - Prob. 20.25SPCh. 20 - Give both IUPAC names and common names for the...Ch. 20 - Draw the structures of the following compounds. a....Ch. 20 - Prob. 20.28SPCh. 20 - Arrange each group of compounds in order of...Ch. 20 - Predict the products (if any) of the following...Ch. 20 - Rank the following isomers in order of increasing...Ch. 20 - Prob. 20.32SPCh. 20 - What do the following pKa values tell you about...Ch. 20 - Given the structure of ascorbic acid (vitamin C):...Ch. 20 - Prob. 20.35SPCh. 20 - Show how you would accomplish the following...Ch. 20 - Predict the products and propose mechanisms for...Ch. 20 - Prob. 20.38SPCh. 20 - Prob. 20.39SPCh. 20 - Prob. 20.40SPCh. 20 - Prob. 20.44SPCh. 20 - Prob. 20.45SPCh. 20 - Predict the major form of each compound when it is...
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- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph -Ph Ph Ph Brarrow_forwardWrite an equation for the acid-base reaction between 2,4-pentanedione and sodium eth- oxide and calculate its equilibrium constant, K. The pK, of 2,4-pentanedione is 9; that of ethanol is 15.9. CH,CCHÖCH, + CH,CH,O Na* H 2,4-Pentanedione Sodium ethoxidearrow_forwardSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBr3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph CH CH o 0om ilubongo CEC-Ph In questions 14-24, write the products of the following transformations. If there is no reaction write NR. Indicate R or S or racemic or indicate cis or trans where appropriate OH + LDA THF solvent (S) Pharrow_forward
- Consider a ternary (three-component) system of amphiphile, hydrocarbon, and water. What structure do you expect to form if small amounts of the first two components are mixed with a large amount of water?arrow_forwardGive 2 different one-step methods to convert propanoic acid to methyl propanoate.arrow_forwardWHich statement is true? Statement 1: When phenol is reacted with phthalic anhydride in the presence of sulfuric acid, the solution will turn pink due to phenolphthalein. Statement 2: In the Ferric Chloride Test, the ferric ion forms a violet complex with phenols.arrow_forward
- Give the product of the following reaction. HCIarrow_forwardBecause 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.arrow_forwardRestate the paragraph. The main objective of the laboratory activity was to make aspirin also known as acetylsalicylic acid in its scientific name. It was successfully done as aspirin was synthesized using the combination of salicylic acid and acetic anhydride. In this reaction, salicylic acid's hydroxyl group on the benzene ring interacted with acetic anhydride to generate an ester functional group. This is an esterification reaction that produces acetylsalicylic acid. Sulfuric acid was utilized as a catalyst to start the esterification reaction. Some unreacted acetic anhydride and salicylic acid, as well as sulfuric acid, aspirin, and acetic acid, remained in the solution after the reaction was completed. The process of crystallization was used to obtain pure crystals of a substance from an impure mixture. Upon completion of the lab, analysis, and calculations, , it is evident that the synthesis of aspirin is possible using these methods but that the yield will be relatively lowarrow_forward
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