Concept explainers
The 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
• 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.
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Organic Chemistry: A Guided Inquiry
- 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)arrow_forwardFor 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).arrow_forwardSummarize the relationship between pKa and acid strength by completing the following sentences: a. The higher the pKa of an acid, the stronger or weaker the acid. b. The lower the pKa of an acid, the stronger or weaker the acid.arrow_forward
- For the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.arrow_forwardAs 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.arrow_forwardAnswer 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.arrow_forward
- Using the table of pKa values given in Appendix I, answer the following: a. Which is the most acidic organic compound in the table? b. Which is the least acidic organic compound in the table? c. Which is the most acidic carboxylic acid in the table? d. Which is more electronegative: an sp3 oxygen or an sp2 oxygen? (Hint: Pick a compound in Appendix I with a hydrogen attached to an sp2 oxygen and one with a hydrogen attached to an sp3 oxygen and compare their pKa values.) e. Which compounds demonstrate that the relative electronegativities of a hybridized nitrogen atom are sp 7 sp2 7 sp3?arrow_forwardrank the following species in order of increasing acidity. least acidic should be on top. CBrH2COOH CBr2HCOOH CH3COOH CBr3COOHarrow_forwardFosamax has six acidic groups. The active form of the drug, which has lost two of its acidic protons, is shown in the box. (Notice that the phosphorus atom in Fosamax and the sulfur atom in Problem 36 can be surrounded by more than eight electrons because P and S are below the second row of the periodic table.) a. Why are the OH groups bonded to phosphorus the strongest acids of the six groups? b. Which of the remaining four groups is the weakest acid?arrow_forward
- a. Which of the halide ions (F - , Cl - , Br - , and I - ) is the most stable base? b. Which is the least stable base?arrow_forwardProivde your view on this "The acidity of HA increases when the conjugate base A:− is resonancestabilized" ?arrow_forwardWhat is the weaker base, NH3 or NaNH2?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning