Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 17.2, Problem 4P
Rank the following substances in order of increasing acidity:
(a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH
(b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol
(c) Benzyl alcohol, phenol, p-hydroxybenzonic acid
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Benzoic acid (C6H5COOH) and aniline (C6H5NH2) areboth derivatives of benzene. Benzoic acid is an acid withKa = 6.3 x10-5 and aniline is a base with Ka = 4.3 x10-10.
(a) What are the conjugate base of benzoic acid andthe conjugate acid of aniline? (b) Anilinium chloride(C6H5NH3Cl) is a strong electrolyte that dissociates intoanilinium ions (C6H5NH3+) and chloride ions. Which willbe more acidic, a 0.10 M solution of benzoic acid or a 0.10M solution of anilinium chloride? (c) What is the value ofthe equilibrium constant for the following equilibrium?C6H5COOH(aq) + C6H5NH2(aq) ⇌ C6H5COO-(aq) + C6H5NH3+(aq)
(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is
formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the
structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it
is dispensed under strict controls because it also causes birth defects.
PPha
NaOCH,CH3
HO-
isotretinoin
HO
A
Br
X
Y
Consider the two following nitrophenol structures:
OH
OH
`NO2
NO2
p-nitrophenol
m-nitrophenol
Predict which will be the stronger acid. (Hint: Consider
possible resonance structures analogous to those given in
the text for phenol.)
Chapter 17 Solutions
Organic Chemistry
Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2PCh. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5PCh. 17.3 - Prob. 6PCh. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8PCh. 17.5 - Prob. 9PCh. 17.5 - Prob. 10P
Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
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
- Which of the following compounds are acidic (A), basic (B), or relatively neutral (N). CH;-CH-S-H CH;-CH2-CH3 CH;-CH=CH2 CH;-CH,-0-CH, CH;-CH2-O-Harrow_forwardWhich pair is not a conjugate acid–base pair?(a) (CH3)3 N; (CH3)3 NH+ (b) H2SO4; H2SO3 (c) HNO2; NO2-arrow_forward1) Complete the following reactions and identify the acid, base, conjugate acid and conjugate base. CH;CH,NH2 (aq) + H2O (1) a) CH;COOH (aq) + H,O (I) b) c) Identify the conjugate base and conjugate acid of each of the following. Conjugate Base Molecule Conjugate Acid HCO3 H20 HSO4- H2PO4arrow_forward
- Predict the stronger acid in each pair: (a) HCl or HF;(b) H3PO4 or H3AsO4; (c) HBrO3 or HBrO2; (d) H2C2O4 orHC2O4-; (e) benzoic acid (C6H5COOH) or phenol (C6H5OH).arrow_forwardWrite equations for the following acid-base reactions.(a) HCOOH + -CN (b) CH3COO- + CH3OH(c) (CH3)2CHOH + NaNH2 (d) NaOCH3 + HCNarrow_forward3. For the following acid - base reaction, (a) predict the products; (b) identify the Bronsted acid, Bronsted base, conjugate acid, and conjugate base; (c) use curved arrows to show the flow of electron pairs in the reaction. CH3 CH2C-OH + NaNHaarrow_forward
- Consider the following reaction: (a) What is the acid on the left side of the equation? (b) What is the base on the left side of the equation? (c) What is the conjugate base of the acid on the left? (d) What is the conjugate acid of the base on the left? (e) What is the acid on the right side of the equation? (f) What is the base on the right side of the equation? (g) What is the conjugate base of the acid on the right? (h) What is the conjugate acid of the base on the right?arrow_forwardThe following aqueous species constitute two conjugate acid-base pairs. Use them to write one acid-base reaction with Kc > 1 and another with Kc < 1: HS-, Cl-, HCl, H2S.arrow_forwardPredict the stronger acid in each pair: (a) HNO3 or HNO2;(b) H2S or H2O; (c) H2SO4 or H2SeO4; (d) CH3COOH or CCl3COOH.arrow_forward
- Arrange the following compounds in increasing order in terms of acidity. CH3CH2SH, PhSH, RSO3Harrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forward2-methylvaleric acid, CH3(CH2)2CH(CH3)COOH, has a pKa=4.9. draw the skeletal structure of the conjugate base of 2-methylvakeric acid and give the pH above which 90% of the compound will be in this conjugate base form.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY