Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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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?
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Chapter 8 Solutions
Organic Chemistry
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
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