Organic Chemistry
7th Edition
ISBN: 9780321826596
Author: Bruice, Paula Yurkanis/
Publisher: Pearson College Div
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 6.5, Problem 9P
The pKa of a protonated alcohol is about –2.5, and the pKa of an alcohol is about 15. Therefore, as long as the pH of the solution is greater than ___ and less than ________, more than 50% of 2-propanol (the product of the reaction on p. 244) will be in its neutral. nonprotonated form.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Write TRUE if the underlined word/phrase makes the statement correct. Otherwise, write the correct WORD/PHRASE that will make the statement true.
a. 2-phenylacetaldehyde is soluble with concentrated sulfuric acid due to acid-base neutralization.
b. 2-phenylacetic acid has a solubility classification of A2, which means it is soluble in 5.O%NaOH and insoluble in 5.O% NaHCO3.
c. Scratching the inner sides of the beaker to begin recrystallization is advised for unsaturated solutions.
d. Washing with hot solvent eliminates adhered mother liquor and avoids crystal dissolution.
e. To extract a nonpolar organic compound using solvent extraction, the extracting solvent must be nonpolar, and the washing solvent must be also nonpolar.
f. Addition of 6.0 M NaCl extracts saponins by converting them to their salt form.
g. The stationary phase in the paper chromatography experiment is the filter paper.
h. When the spots have low concentration, they will not be observed as visible spots in the…
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.
Why does the dehydration of an alcohol more often use concentrated sulfuric acid,
H2SO4H2SO4, as the acid catalyst rather than dilute hydrochloric acid,
HCl?
Select one or more:
Hydrochloric acid is too small to effectively react with the alcohol in the reaction.
The additional water solvent from a dilute solution could reverse the dehydration reaction.
Only acids with more than one proton can complete the dehydration reaction.
The presence of the chloride ion could result in a competing substitution reaction.
Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are avilable for...Ch. 6.2 - Prob. 3PCh. 6.2 - Prob. 4PCh. 6.3 - Prob. 5PCh. 6.4 - Prob. 6PCh. 6.4 - What alkene should be used to synthesize each of...Ch. 6.4 - Prob. 8PCh. 6.5 - The pKa of a protonated alcohol is about 2.5, and...Ch. 6.5 - Prob. 10P
Ch. 6.5 - Prob. 11PCh. 6.6 - a. What is the major product or each or the...Ch. 6.6 - Prob. 14PCh. 6.6 - Prob. 15PCh. 6.7 - What is the major product obtained from the...Ch. 6.8 - Which is more highly regionselective: reaction of...Ch. 6.8 - Prob. 19PCh. 6.9 - What will be the product of the preceding reaction...Ch. 6.9 - Prob. 21PCh. 6.9 - Prob. 22PCh. 6.9 - Prob. 23PCh. 6.9 - What is the product of the addition of 1Cl to...Ch. 6.9 - What will be the major product obtained from the...Ch. 6.9 - Propose a mechanism for the following reaction:Ch. 6.10 - Draw structures for the following: a. 24...Ch. 6.10 - What alkene would you treat with a peroxyacid in...Ch. 6.11 - What products are formed when the following...Ch. 6.11 - Prob. 30PCh. 6.11 - Prob. 31PCh. 6.12 - Prob. 34PCh. 6.12 - Prob. 35PCh. 6.13 - Prob. 36PCh. 6.13 - Prob. 37PCh. 6.13 - Prob. 38PCh. 6.14 - What characteristics must the reactant of a...Ch. 6.15 - Prob. 40PCh. 6.15 - What stereoisomers are obtained from each of the...Ch. 6.15 - Prob. 45PCh. 6.15 - Prob. 46PCh. 6.15 - Prob. 47PCh. 6.15 - Prob. 49PCh. 6.15 - Prob. 50PCh. 6.15 - Prob. 51PCh. 6.15 - Prob. 52PCh. 6.15 - Prob. 53PCh. 6.16 - Prob. 54PCh. 6.17 - Prob. 55PCh. 6.18 - Explain why 3-methykyclohexene should not be used...Ch. 6.18 - Prob. 58PCh. 6 - Prob. 59PCh. 6 - Prob. 60PCh. 6 - What is the major product of the reaction of...Ch. 6 - Give two names for each of the following:Ch. 6 - Prob. 63PCh. 6 - Prob. 64PCh. 6 - Prob. 65PCh. 6 - What are the products of the following reactions?...Ch. 6 - When 3-methyl-1-butene reacts with HBr, two alkyl...Ch. 6 - Prob. 68PCh. 6 - Draw curved arrows to show the flow of electrons...Ch. 6 - What reagents are needed to carry out the...Ch. 6 - Prob. 71PCh. 6 - Prob. 72PCh. 6 - Prob. 73PCh. 6 - Prob. 74PCh. 6 - a. Draw the product or products that will be...Ch. 6 - The second-order rate constant (in units of M1s1)...Ch. 6 - Which compound has the greater dipole moment?Ch. 6 - Prob. 78PCh. 6 - Prob. 79PCh. 6 - Prob. 80PCh. 6 - Prob. 81PCh. 6 - Prob. 82PCh. 6 - Prob. 83PCh. 6 - Prob. 84PCh. 6 - Prob. 85PCh. 6 - Prob. 86PCh. 6 - Prob. 87PCh. 6 - Prob. 88PCh. 6 - Prob. 89PCh. 6 - Prob. 90PCh. 6 - 91. a. How many alkenes could you treat with H2,...Ch. 6 - Draw the products of the following reactions. If...Ch. 6 - Prob. 93PCh. 6 - Prob. 94PCh. 6 - Two chemists at Dupont found that lCH2Znl is...Ch. 6 - Prob. 96PCh. 6 - Prob. 97PCh. 6 - What alkene gives the product shown after...Ch. 6 - Prob. 99PCh. 6 - Prob. 100PCh. 6 - Prob. 101PCh. 6 - Prob. 102PCh. 6 - Prob. 103PCh. 6 - Propose a mechanism for the following reaction:Ch. 6 - Prob. 106PCh. 6 - Prob. 107P
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
- 1.1 The density of a gas was measured at 1 50 atm and 27 degree celsuis and found to be 1 95 g/L. Calculate the molar mass of the gas. 1.2 Draw and name three structural isomers of octane (C8H18) 1.3 State Markonikov's rule 1.4 The base Ca(OH)2 is almost insoluble in water , only o 25 g can be dissolved in 0.5 L of water at 25 degree celsuis. If the dissolved substance is completely dissociated into constuent ions , what is the pH of the solution?arrow_forwardg. Write a balanced equation for the reaction that takes place between the organic product from part f and NaOH(aq). h. Draw the name of the products that form when the acid from part a is heated in the presence of (CH3CH2)2NH. i. Write a balanced equation for the reaction that takes place when the organic product from part h is heated in the presence of H2O and H+.arrow_forwardWe have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as theiractive species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, beforeand after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygendoes each atom have before and after the oxidation?(a) the Cr in chromic acid (b) the Cl in sodium hypochlorite(c) the S in the Swern oxidation (d) the I in the DMP reagent(e) the carbinol C in the alcohol that is oxidizedarrow_forward
- THE ZnCl2 / HCl TEST DETERMINES THE REACTIVITY OF ALCOHOLS. ORDER IN ORDER FROM GREATEST TO LOWEST REACTIVITY METHANOL-TERBUTANOL-2PROPANOL TERBUTANOL-METHANOL-METHANOL METHANOL-2 PROPANOL-TERBUTANOLarrow_forwardMixing cyclohexanol with phosphoric acid is an exothermic process, whereas the production of cyclohexene is endothermic. Construct an energy diagram showing the course of this reaction. Label the diagram with the starting alcohol, the oxonium ion (the protonated alcohol), the carbocation, and the product.arrow_forwardwhich compound(s) would remain in an organic phase if we used aqueous NaOH? the neutral compund the basic compound the acid compoundarrow_forward
- Determine whether the alcohol is primary, secondary or tertiary. a. An alcohol rapidly evolved hydrogen gas when treated with sodium metal. It rapidly changed the color of potassium dichromate solution but did not form a cloudy layer when treated with ZnCl2 in HCl. b. An alcohol that did not evolve hydrogen gas and did not change the color of potassium dichromate solution but rapidly formed a cloudy layer when treated with concentrated ZnCl2 in HCl. c. An alcohol that evolved hydrogen gas at moderate speed and changed the color of potassium dichromate solution and formed a cloudy layer when treated with ZnCl2 in HClarrow_forwardModified true or false. If statement is true, write TRUE, otherwise change the italicized words/phrases in the statement. Cations in hard water like Ca2+ and Mg2+ can form precipitates with carboxylates in soaps, reducing their efficiency as cleansing agents. If an ester is to be prepared with ethanol, using at least 70% ethanol could maximize the yield.arrow_forward*Enumerate the classes of organic derivatives of water that are soluble in concentrated H2SO4arrow_forward
- What kind of solvent ingredients is usually used in the concentrations of 4-10 percent in skin care products and their function is to soften skin cells and to lessen wrinkles? A. Ethly acetate B. Alpha hydroxyl acids C. Phenols and phenol derivatives D. Aliphatic alcoholsarrow_forward1. Which of the following is NOT a true statement? A. Tartaric acid is present in grapes B. Acetic acid is present in sour milk C. Citric acid is a tricarboxylic acid D. Formic acid is present in insect bites 2. The greater acidity of carboxylic acids compared to alcohols arises primarily from: A. the electron-withdrawing effect of the carboxyl oxygen B. the electron-donating effect of the hydroxyl group C. the acidity of a hydrogens of carboxylic acids D. the resonance stability associated with the carboxylate ion 3. Amides are commonly prepared by reacting acyl halides, esters, or anhydrides with? A. Tertiary amines B. Ammonium hydroxide Please answer all thank you C. Ammonium chloride D. Ammoniaarrow_forwardPlease help in answering the following questions ~Which of the following is the basis of the classification of alcohols?A. Based on the number of hydroxyl groups attached.B. Based on the number of carbon atoms which are directly attached to the carbon thatis bonded with the -OH group.C. BothD. Neither ~Which of the following carboxylic acids will yield the least amount of protons in an aqueoussolution?A. 2-chlorobutanoic acidB. Propanoic acidC. Butanoic acidD. 2-methylbutanoic acidarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks ColeOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Acid-Base Titration | Acids, Bases & Alkalis | Chemistry | FuseSchool; Author: FuseSchool - Global Education;https://www.youtube.com/watch?v=yFqx6_Y6c2M;License: Standard YouTube License, CC-BY