f) The reason why acetic acid is more acidic thanethanol. Draw the conjugate bases for eachcompound and identify the key factor thatstabilizes one conjugate base and not the other.ethanolacetic acidpK, = 16pK, = 5h) Provide a base that will completely deprotonatepropyne (K > 10³) and the conjugate acid of yourbase. Provide the pKa of propyne and the pKa ofthe conjugate acid of your base and calculate theequilibrium constant.H3C-=H ++ H3C =: Liconjugate acidof your baseyour basepk =pKa =K=

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Answered: f) The reason why acetic acid is more…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 20CTQ

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1) Consider the reaction AH+ H₂O A:+H3O¹. For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa value of the acid in multiples of 5, 3) give the name of the conjugate base, and 4) draw the structure of the conjugate base. m-Chlorophenol 3-Pentanone acid Conj. base acid Conj. base pKa Benzoic acid pka_ iso-Butyl ammonium ion pka_ Diethyl Malonate pka_ Benzyl oxonium ion pka_ 1-pentyne pKa pKa Ethyl Acetate pKa
Using 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.
conjugate base acid Consider the reaction AH + H2O 5 A: + H3O+. For the following named acids: a) draw the structure of the acid, b) give the approximate pKa value of the acid in multiples of 5, and c) draw the structure of the conjugate base. pKa sec-Butyl ammonium ion Cyclohexanone pKa iso-Butyl alcohol pKa N-ethylcarbamic acid pKa
According to the Evan's pKa table, phenol has a pKa of 9.95. p-Nitro and m-nitrophenol have pKas of 7.14 and 8.35 respectively. Using resonance structures, explain the observed trends in the acidity of these molecules.
4 5 Arrange the following bases in increasing base strength. There is no partial credit on this problem. Weakest base 1 2 3 Pyridine (C5H5N), Kb = 1.7 x 10-⁹ Aniline (C6H5NH2), Kb = 3.9 x 10-10 Strongest base Methylamine (CH3NH₂), Kb = 4.4 x 10-4 Hydrazine (N2H4), Kb = 1.3 x 10-6 ⠀ Dimethylamine ((CH3)2NH), K₂ = 5.1 x 10-4
Fix each molecule in the drawing area below so that it has the structure it would have if it were dissolved in a 0.1 (aq) solution of NaOH 3-hydroxypropanoic acid and 1,3-dihydroxy-2-propanone .
B) Consider the reaction Bi() + H3O* → BH + H20. For the following named bases: a) draw the structure of the base, b) draw the structure of the conjugate acid, and c) give the approximate pKa of the conjugate acid. Ethoxide Triethylamine Pyridine
Propose you are given a mixture of naphthalene, propanoic acid, and diethyl amine. Explain, using a flow chart similar to that in #1, how you would separate these three compounds. Include all solvents and reagents, show the exact compound that is present at each juncture, and be clear about the experimental technique employed in each step.
Amines are weak bases. Table 10.2 in the course textbook provides a list of pKb values for several amines. The pK values for three amines and their structures are shown below. Explain why increased substitution on nitrogen results in an increase of the pKb value. H3C-NH2 PK = 3.36 H3C N-H pKb = 3.27 H₂C' H3C N-CH3 PK = 4.19 H₂C
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)
Trifluoroethanol (CF3CH2OH, pKa = 12.5) is more acidic than ethanol (CH3CH2OH, pKa = 16). Provide a three-dimensional structure for each conjugate base and draw the orbitals for all lone pairs. Provide a succinct explanation for the greater acidity of trifluoroethanol.
Arrange 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.

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