Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Videos
Question
Chapter 17, Problem 17.55AP
Interpretation Introduction
(a)
Interpretation:
The reason as to why triphenylmethane is a strong hydrocarbon acid is to be stated.
Concept introduction:
Acidity of a compound is its tendency to donate a proton. It depends upon the formation of the stable conjugate base or stable carbanion. Stronger the conjugate base, weaker is the acid and vice versa.
Interpretation Introduction
(b)
Interpretation:
The reason as to why fluoradene is more acidic than triphenylmethane is to be stated.
Concept introduction:
Acidity of a compound is its tendency to donate a proton. It depends upon the formation of the stable conjugate base or stable carbanion. Stronger the conjugate base, weaker is the acid and vice versa.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(c)
Arrange the following compounds in order of increasing acidity, and explain the reasons for
your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.
The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much?
b) What is the proportion of the fluorenide anion to fluorene?
(c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?
(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-enal
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - Prob. 17.2PCh. 17 - Prob. 17.3PCh. 17 - Prob. 17.4PCh. 17 - Prob. 17.5PCh. 17 - Prob. 17.6PCh. 17 - Prob. 17.7PCh. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22APCh. 17 - Prob. 17.23APCh. 17 - Prob. 17.24APCh. 17 - Prob. 17.25APCh. 17 - Prob. 17.26APCh. 17 - Prob. 17.27APCh. 17 - Prob. 17.28APCh. 17 - Prob. 17.29APCh. 17 - Prob. 17.30APCh. 17 - Prob. 17.31APCh. 17 - Prob. 17.32APCh. 17 - Prob. 17.33APCh. 17 - Prob. 17.35APCh. 17 - Prob. 17.36APCh. 17 - Prob. 17.37APCh. 17 - Prob. 17.38APCh. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Prob. 17.42APCh. 17 - Prob. 17.43APCh. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Prob. 17.46APCh. 17 - Prob. 17.47APCh. 17 - Prob. 17.48APCh. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Prob. 17.54APCh. 17 - Prob. 17.55APCh. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Prob. 17.58APCh. 17 - Prob. 17.59AP
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
- (a) Draw the structure of the following :(i) p-Methylbenzaldehyde (ii) 4-Methylpent-3-en-2-one(b) Give chemical tests to distinguish between the following pairs of compounds :(i) Benzoic acid and Ethyl benzoate, (ii) Benzaldehyde and Acetophenone.(iii) Phenol and Benzoic acid.arrow_forwardGive reasons for the following: (i) p-nitrophenol is more acidic than p-methylphenol. (ii) Bond length of C—O bond in phenol is shorter than that in methanol. (iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward
- Write the equilibrium-constant expressions and obtain numerical 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 ammonium hydrochloride, CH3NH3Cl. (d) the basic dissociation of NaNO2. (e) the dissociation of H3AsO3 to H3O+ and AsO33- just answer the letters C, D and E.arrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.(a) isobutylene and HF (b) cyclohexanol and BF3 (c) fuming sulfuric acidarrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward
- Explain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.arrow_forward(c) Arrange the following compounds in order of increasing acidity, and explain the reasons fo your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluoronhenolarrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forward
- (a) Give the products of the phosphoric acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Label the three products with major, minor, and trace amounts. OH H3PO4, heat (b) Describe the rule that is applied in the acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Explain your answer based on the products formed.arrow_forwardIdentify (A) in the following reaction. 2H2 Pt (A) KMNO4 Warm conc. || С — С — о—н |CO,H + HO CO2H cis-cyclo hexane 1,2-dicarboxylic acid (a) (b) (c) (d)arrow_forward5. (a) HF is an acid. What is it's conjugate base ? (b) CIO₂ is a base. What is it's conjugate acid ? (c) What is the conjugate base of H₂PO4¹ ? (d) What is the conjugate acid of H₂PO4-¹ ?arrow_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