The most acidic proton on the molecule below has pK, 17. Which of the following bases are capable of deprotonating the proton? Check all that apply. Note: Reference the pK of selected organic compounds table for additional information. Acid CH₂CH₂OH 16 H₂CO3 H₂O H₂ C4H10 PK value H 6.4 14 35 50

The most acidic proton on the molecule below has pK, 17. Which of the following bases are capable of deprotonating the proton? Check all that apply. Note: Reference the pK of selected organic compounds table for additional information. Acid CH₂CH₂OH 16 H₂CO3 H₂O H₂ C4H10 PK value H 6.4 14 35 50

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.21P: Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The...

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16-27 Guanidine, p/Ca 13.6, is a very strong base, almost as basic as hydroxide ion. NH NH2+ II II H2N—C—NH2 + H2O H2N—C—NH2 + OH" Guanidine Guanidinium ion pKb = 13.6 Complete the Lewis structure for guanidine, showing all valence electrons. The remarkable basicity of guanidine is attributed to the fact that the positive charge on the guanidinium ion is delocalized by resonance over the three nitrogen atoms. This delocalization increases the stability of the guanidinium ion relative to the ammonium ion or substituted ammonium ions. Draw three equivalent contributing structures for the guanidinium ion and show by the use of curved arrows how these three contributors are related. Propose an explanation for the fact that protonation occurs on the C=NH nitrogen rather than on one of the —NH., nitrogens. (Hint: Consider the resonance stabilization of the structure formed by protonation on a —NH., nitrogen compared with the resonance stabilization of the structure formed by protonation on the =NH nitrogen.) Predict the N—C—N bond angles in the hybrid. Which is the stronger acid, the ammonium ion or the guanidinium ion?
Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.
Complete a net ionic equation for each proton-transfer reaction using curved arrows to show the flow of electron pairs in each reaction. In addition, write Lewis structures for all starting materials and products. Label the original acid and its conjugate base; label the original base and its conjugate acid. If you are uncertain about which substance in each equation is the proton donor, refer to Table 4.1 for the relative strengths of proton acids. (a) NH3+HCl (b) CH3CH2O+HCl (c) HCO3+OH (d) CH3COO+NH4+
Which has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acid
Classify each of the following substances into the appropriate category: 1 Lewis acid; 2 Lewis base; 3 substance that can act as either a Lewis acid or Lewis base; 4 substance that is neither a Lewis acid nor a Lewis base. a CCl4,b F, c Cu2+, d Fe3+, e O2
H₃PO₄ is a polyprotic acid with three acidic protons. Identify the products of the second acid dissociation of H₃PO₄ in water.
Which of the following two acids has the stronger conjugate base? Nitrous acid, Ka = 7.1 x 10–4 Phenol, Ka = 1.0 x 10–10 The strength of the conjugate base cannot be obtained from the information given. Nitrous acid, because it has a larger Ka value. Nitrous acid, because it has a smaller Ka value. Phenol, because it has a larger Ka value. Phenol, because it has a smaller Ka value.
Consider the data in the table below to answer the following questions: Which of the acids in the table above has the strongest conjugate base? Your answer Acidities of Substituted Benzoic and Acetic Acids pks at 25°C Y Y CIL₂COOT meta H 4.75 4.19 CN 2.47 3.64 OCH, 3.57 4.09 What is the structure of the strongest acid in the table above? Your answer Y CH₂COOH para 4.19 3.55 4.46
At what pH will the concentration of a compound with a pK, 8,4 be 100 tímes greater in ita acidic form than in its basic form? Express your answer using one decimal place. pH= 7.9 At what pH will 50% of a compound with a pK, = 7.6 be in its basic form? Express your answer using one decimal place. pH = At what pH will the concentration of a compound with a pK = 4.6 be 10 times greater in its basic form than in its acidic form? Express your answer using one decimal place. pH = Submit Danunet Anenr
Use the information in the pK table to rank the molecules in order of decreasing basicity. For example, select "1" in the second column for the strongest base a and "2" for the next strongest base and so on. CH3 HS F CH,CO, Molecules (Choose one) (Choose one) (Choose one) (Choose one) X Ś CHA 4 NH₂ H₂ CH3NH₂ 2 48 38 36 33 pk table pKa CH,NH, CH₂SH 10.4 H₂O* HCN + 10.6 9.4 NH H₂O 15.7 H₂S CH₂OH 15.5 CH,CO,H 4.76 9.2 7.00 HF CH₂OH₂ H₂SO4 HC1 HBr 3.17 -1.7 -2.2 -3.0 -7 -9
Between these two compounds, Be or CH,O, draw the Lewis structure of the stronger base. pk, values of organic and inorganic acids PK, Acid CH₂CH₂ NH₁ 1₂ 51 38 Ⓡ Acid 35 CHÍCHO 159 CHCOOH H₂O 15.7 H₂O CHÍNH "NH₂ H₂S 7,04 H200, 6.36 CH₂COOH 4.76 10.64 ₂50, 9.24 Hie 9985 pk, -1.74 52 Explicitly draw all Hatoms. . Include all valence lone pairs in your answer. -B d AIP [Ref
Another way to express acid strength is by using pk b:pK a =−logK a Another way to express base strength is by using pK b pK b =−logK b A new potential heart medicine, code-named X-281, is being tested by a pharmaceutical company, Pharma-pill. As a research technician at Pharma-pill, you are told that X-281 is a monoprotic weak acid, but because of security concerns, the actual chemical formula must remain top secret. The company is interested in the drug's K a value because only the dissociated form of the chemical is active in preventing cholesterol buildup in arteries.To find the pK a of X-281, you prepare a 0.079 M M test solution of X-281 at 25.0 ∘ C The pH of the solution is determined to be 3.00. What is the pK a of X-281?