ORGANIC CHEMISTRY 345 WSU >IP<
15th Edition
ISBN: 9781269916264
Author: Pearson
Publisher: PEARSON C
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Textbook Question
Chapter 8, Problem 92P
Protonated cyclohexylamine has a Ka = 1 × 10–11 Using the same sequence of steps as in Problem 94, determine which is a stronger base: cyclohexylamine or aniline.
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Protonated cyclohexylamine has a Ka = 1 X 10-11, determine which is a stronger base: cyclohexylamine or aniline.
Which base would you expect to generate the stronger conjugate acid?
A.) Hydrazine Kb = 1.7 x 10-4
B.) Analine Kb = 4.3 x 10-10
C.) Triethylamine Kb = 1.0 x 10-3
D.) Ammonia Kb = 1.8 x 10-5
Define why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an alpha carbon of an ester? What are their pKa's?
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
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- Which base is considered the strongest? Ammonia Kb = 1.8 x 10-5 Analine Kb = 4.3 x 10-10 Triethylamine Kb = 1.0 x 10-3 Hydrazine Kb = 1.7 x 10-4arrow_forwardPut the following compounds in order from weakest acid to strongest acid. Explain (pKa values are not enough and trends should be considered).arrow_forwardUsing pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward
- You are planning to carry out a reaction that produces protons. The reaction will be buffered at pH = 10.5. Would it be better to use a protonated methylamine/methylamine buffer or a protonated ethylamine/ethylamine buffer? (pKa of protonated methylamine = 10.7; pKa of protonated ethylamine = 11.0)arrow_forwardWhich acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.arrow_forwardcalculate the lambda max Base Table: Heteroannular - 214nm Homoannular - 253nm Butadiene System - 217nm Acyclic trienes - 245nm alkyl +5 secondary amine +60 extending conjuction +30 exocyclic double bond +5 acetate +0 ether +6 thioether +30 double bond +5 Br, Cl +5arrow_forward
- Given 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?arrow_forwardArrange the compounds in each set in order of increasing base strength. consult Table 4.1 for pKa values of the conjugate acid of each base.arrow_forwardWhich species is the stronger Lewis Acid? Why? (Use resonance structures to explain your answer.) BH3 or trimethoxyboratearrow_forward
- 3. Rank the following acids in order from strongest to weakest.HA (pKa = 2.55) H2Z (pKa1 = 4.35) H3X (pKa1 = 3.17) HY (pKa = 5.72) 4. Rank each base in order from strongest to weakest.B (pKb = 4.12) Y– (pKa = 5.72 for conjugate acid) A– (pKa = 2.55 for conjugate acid)E (pKb = 8.12)arrow_forwardDetermine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products:(a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forwardGiven the following information determine which of these acids is the strongest? Ka for boric acid is 7.3 x 10–10 pKa of acetic acid is 4.75 Ka for lactic acid is 8.4 x 10–4 pKa of phenol is 9.89 A acetic acid B formic acid C lactic acid D phenolarrow_forward
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