Interpretation:
The stability of
Concept introduction:
A protic solvent can solvate both cation and anion, but an aprotic solvent can solvate only cation and not anions. The protic solvent is a compound containing at least one hydrogen atom bonded to an electronegative atom of oxygen, nitrogen, or fluorine and capable of forming a hydrogen bond. The aprotic solvent is a compound which cannot form a hydrogen bond due to the lack of hydrogen atom bonded to an electronegative atom of oxygen, nitrogen, or fluorine. The polar solvent molecule has a partial negative and partial positive charge. The negative ends of the solvent’s dipole solvate the cation strongly, and the positive end of the solvent’s dipole solvate the anion strongly. When two positively charged species are present in the solution, the stronger acid is the one that is less stable.
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ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
- The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at a different basic site. Draw the structure of the actual conjugate acid of acetamide, and explain (resonance) why protonation occurs where it does rather than on nitrogen. Calculate the pKa of this conjugate acid.arrow_forwardAcetic acid can also react as a very weak base (pKb = 20). Two different sites on acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is more stable. Calculate the pKa of this conjugate acid.arrow_forwardIn each of the following reactions, one of the reagents contains two reactive groups (either acidic or basic). You have to decide which group will be affected under mentioned conditions. To answer this problem correctly I suggest that you use the following strategy: (i) Write the products of the reaction: conjugate acid and conjugate base. Use curved arrows to track the flow of electrons; (ii) Using Table 3.1 of the textbook estimate and write pKa values for all acidic groups you have in the reaction equation including conjugate acid; (iii) If you wrote the correct reaction the estimated pKa values should confirm that the reaction transformation changes stronger acid to weaker acid and stronger base to weaker.arrow_forward
- Experimental observations show that thiocyanate (SCN- ), the conjugate base of thiocyanic acid (pKa = 1.1 at 25 °C), is quite soluble in neutral water at pH > 2. In the space provided below, explain this experimental observation. That is, why does SCN– readily dissolve in water when the pH > 2?arrow_forwardDiscuss comprehensively why -Cl and -NO2 aredeactivators and why -Cl is a weak and -NO2 astrong deactivator?arrow_forwardNaNH2 is typically used instead of KOH to produce alkynes through elimination because NaNH2 is a stronger base. Explain why KOH can be used to create diphenylacetylene.arrow_forward
- Verify that the equilibrium position for the reaction between phenol and hydroxide ion is on the right by comparing the pKa value of the acid on the left with that of the acid on the right. Which acid is stronger? do the same for the reaction of phenol with hydrogen carbonate ionarrow_forwardWhich is a stronger acid and has the most stable conjugate base? Estimate the pKA values for both compounds.arrow_forwardExplain why the heat of neutralization involving acetic acid and hydroxidesodium is lower than the value found in the neutralization reaction involving hydrochloric acid and the sodium hydroxide.arrow_forward
- pKa of CF3CH2OH is higher than the pKa of a CCl3CO2H. Provide the reason Group of answer choices a) The conjugate base of CCl3CO2H is more stabilized than the conjugate base of CF3CH2OH b) The conjugate base of CCl3COH is stabilized by type of atom c) CF3CH2OH is stronger acid d) The conjugate base of CCl3CO2H is less stabilized than the conjugate base of CF3CH2OH e) Fluorine is more electronegative than Clarrow_forwardWhich of the following statement is INCORRECT? a. Electron-withdrawing group near the carboxylate ion reduces its stability thereby acidity is reduced. b. Electron-withdrawing group near the carboxylate ion increase acidity and also contributes to the stability. c. Electron-donating groups decrease acidity by destabilizing the carboxylate ion. d. A carboxylate ion is much more stable than the corresponding alkoxide ion because of the existence of resonance structures for the carboxylate ion which disperse its negative charge.arrow_forwardOne of the heptanedione isomers below has a pka of approximately 9 rather than 20. Which isomer? Why? Draw its conjugate base and offer a full explanation of its acidity.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning