ORGANIC CHEMISTRY 345 WSU >IP<
15th Edition
ISBN: 9781269916264
Author: Pearson
Publisher: PEARSON C
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 8, Problem 91P
The acid dissociation constant (Ka) for loss of a proton from cyclohexanol is 1 × 10–16
- a. Draw a reaction coordinate diagram for loss of a proton from cyclohexanol.
- b. Draw the resonance contributors for phenol.
- c. Draw the resonance contributors for the phenolate ion.
- d. On the same plot with the energy diagram for loss of a proton from cyclohexanol, draw an energy diagram for loss of a proton from phenol.
- e. Which has a greater Ka: cyclohexanol or phenol?
- f. Which is a stronger acid: cyclohexanol or phenol?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
The pKa of our product is ~ 2-3 units lower than the pKa of phenol. Draw all possible resonance structures of the conjugate base of the product, and use these to explain why our product is so much more acidic than phenol.
The Ka of acetic acid (CH3CO2H) is 1.8x10-5 and the Kb of methylamine (CH3NH2) is 4.4x10-4. Complete the following equilibrium reaction (acid-base reaction) equation and predict the side of the equilibrium that is favored. Explain. Show all your work.
Consider the series of the trans effect:
CO, CN-, C2H4 > PR3, H-, CH3- > C6H5- > NO2-, SCN-, I- > Br- >Cl- > py > NH3 > H20
What would be the major product of the following reaction?
Select one:
Chapter 8 Solutions
ORGANIC CHEMISTRY 345 WSU >IP<
Ch. 8.1 - Prob. 1PCh. 8.1 - Prob. 2PCh. 8.4 - Prob. 3PCh. 8.5 - Prob. 5PCh. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 7PCh. 8.6 - Prob. 8PCh. 8.8 - Prob. 9PCh. 8.9 - Prob. 10PCh. 8.9 - Prob. 12P
Ch. 8.9 - Prob. 13PCh. 8.10 - Prob. 14PCh. 8.10 - What orbitals contain the electrons represented as...Ch. 8.10 - Prob. 16PCh. 8.10 - Prob. 17PCh. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.11 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.12 - Prob. 22PCh. 8.12 - Prob. 23PCh. 8.13 - Prob. 24PCh. 8.13 - Prob. 25PCh. 8.13 - Prob. 26PCh. 8.14 - Prob. 27PCh. 8.14 - Prob. 28PCh. 8.14 - Prob. 29PCh. 8.15 - Which member of each pair is the stronger acid?Ch. 8.15 - Which member of each pair is the stronger base? a....Ch. 8.15 - Rank the following compounds from strongest acid...Ch. 8.15 - Prob. 34PCh. 8.16 - Prob. 35PCh. 8.17 - Prob. 37PCh. 8.17 - Prob. 38PCh. 8.17 - Prob. 39PCh. 8.17 - Prob. 40PCh. 8.17 - Prob. 41PCh. 8.17 - Prob. 42PCh. 8.18 - Prob. 43PCh. 8.18 - Prob. 44PCh. 8.18 - Prob. 45PCh. 8.18 - Prob. 47PCh. 8.19 - Prob. 48PCh. 8.19 - Prob. 49PCh. 8.19 - Prob. 50PCh. 8.19 - Prob. 51PCh. 8.19 - Prob. 52PCh. 8.19 - Prob. 53PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - Prob. 67PCh. 8 - Prob. 68PCh. 8 - Prob. 69PCh. 8 - Which compound is the strongest base?Ch. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Prob. 74PCh. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - Prob. 77PCh. 8 - Prob. 78PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 80PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 82PCh. 8 - Prob. 83PCh. 8 - Prob. 84PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 86PCh. 8 - a. How could each of the following compounds be...Ch. 8 - Draw the products obtained from the reaction of...Ch. 8 - How would the following substituents affect the...Ch. 8 - Prob. 90PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Prob. 93PCh. 8 - Prob. 94PCh. 8 - Prob. 95PCh. 8 - Prob. 96PCh. 8 - Prob. 97PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 99PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 101PCh. 8 - Prob. 102PCh. 8 - Prob. 103PCh. 8 - Prob. 104PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 8 - Prob. 1PCh. 8 - Prob. 2PCh. 8 - Prob. 3PCh. 8 - Prob. 4PCh. 8 - Prob. 5PCh. 8 - Prob. 6PCh. 8 - Prob. 7PCh. 8 - Prob. 8PCh. 8 - Prob. 9PCh. 8 - Prob. 10PCh. 8 - Prob. 11PCh. 8 - Prob. 12P
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
- The acid dissociation constant (Ka) for loss of a proton from cyclohexanol is 1 X10-16. a. Draw a reaction coordinate diagram for loss of a proton from cyclohexanol.arrow_forward1) Which reaction is likely to be more exergonic, one with Keq = 1000 or one with Keq = 0.001?arrow_forwardIn Part 1, draw the mechanism for the most likely proton transfer reaction between methanol and 2-methylpropanoic acid. In Part 2, indicate which side of the reaction is favored at equilibrium.arrow_forward
- (i) Draw the dissociation reaction for a carboxylic acid in water and define the Ka for this reaction. Write the equation that relates pKa to Ka. (ii) A deprotonated carboxylic acid can be drawn in two resonance forms. Draw the two forms and explain what the term “resonance” means. (iii) Draw an energy profile for the above dissociation reaction and describe how the profiles for a strong and a weak acid would differ.arrow_forwardDraw the enol and the keto forms of the product of the reaction below. Label each as either the enol or the keto form.arrow_forwardOn the same plot with the energy diagram for loss of a proton from cyclohexanol, draw an energy diagram for loss of a proton from phenol. H+OH O−+arrow_forward
- Can you help find the best reagent for this problem?arrow_forwardFor each statement below, label it as causing a faster or slower rate for an E1 reaction. If it doesn’t effect rate at all then label it as neither. Stronger base Increase base concentration Switch leaving group from Cl to I Switch leaving group from 2˚ to 3˚arrow_forwardGiven below are the most important resonance structures for ethyl cinnamate and the product. a) For ethyl cinnamate, draw the next two most favorable resonance structures (ignore resonance with the aromatic ring): 0? b) For your hydrogenation product, draw one more favorable resonance structure:arrow_forward
- Answer each part for the reaction below. a. Draw in ALL missing lone pairs b. Draw appropriate curved arrows to complete the acid-base reaction c. Draw the corresponding products for the reactionarrow_forwardPlease help me asap with the following question, I have a hard time getting itarrow_forwardWhich side of the equilibrium is favored in this acid/base rxn? pka of product: 6.9arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY