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Draw the organic product of the lewis acid-base reaction shwon below. Include all lone pairs and charges as appropriate.
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- Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.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+The following reactions illustrate Brnsted acid-base behavior. Complete each equation. a.HI(aq)+?H3O+(aq)+I(aq) b.NH3(l)+?NH4++NH2 c.H2C2O4(aq)+H2O(l)?+HC2O4(aq) d.H2N2O2(aq)+H2O(l)H3O+(aq)+? e.?+H2O(l)H3O+(aq)+CO32(aq)Summarize the relationship between pKa and base strength by completing the followingsentences: a. For a given base, the higher the pKa of its conjugate acid, the stronger or weaker the base. b. For a given base, the lower the pKa of its conjugate acid, the stronger or weaker the base.
- Use Table 13-2 to order the following from the strongest to the weakest acid. HClO2,H2O,NH4+,HClO4The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.For each molecule below, draw the conjugate acid or conjugate base or both if the molecule hasboth a conjugate acid and a conjugate base (e.g., water).
- Rank the following compounds in order of increasing acidity, and explain your ranking. Br E A A COOH O₂N B COOH (least acidic) < с (most acidic) COOH The strongest acid has a strong electron-withdrawing group base. The weakest acid has a strong electron-donating group H₂C that will D B COOH destabilize that will stabilize the E .COOH Dositive D charge in its conjugate the negative charge in its ARank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (electron donating groups vs electron withdrawing groups), etc.3) а) decreasing acidity and explain your answer. CHCHNΗ Arrange the following compounds in order of CH,CH,OH CH,CH,CH, b) part (a) in order of increasing basicity and explain your Arrange the conjugate bases of the acids given in answer.