you can represent the 'CH5O7' part of citric acid and its derivatives as 'Ci' if you wish. For instance, citric acid would be H3Cİ, citrate ion would be Ci-3, and sodium citrate dibasic would be NazHCi. 3. Circle the acidic hydrogens in the structure above. Hint: when each of these hydrogens leave the molecule, the conjugate base will have more than one resonance structure.

you can represent the 'CH5O7' part of citric acid and its derivatives as 'Ci' if you wish. For instance, citric acid would be H3Cİ, citrate ion would be Ci-3, and sodium citrate dibasic would be NazHCi. 3. Circle the acidic hydrogens in the structure above. Hint: when each of these hydrogens leave the molecule, the conjugate base will have more than one resonance structure.

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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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 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 the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.
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).
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.
Please refer to the molecule shown below when answering questions: Based on relative trends in the periodic table, which function group is more basic, II orVIII?(i) Based on relative trends in the periodic table, which function group is more acidic, II orVII?(j) Because of ring strain, this functional group is likely to undergo ring-opening uponreaction with HCl.
One way to determine the predominant species at equilibrium for an acid-base reaction is to say that the reaction arrow points to the acid with the higher value of pKa. For example,
What is the conjugate acid of each of the following? What is the conjugate base of each? (Omit states-of-matter from your answer.) H2S Conjugate acid= Conjugate base = H2PO4− Conjugate acid= Conjugate base = HSO3− Conjugate acid= Conjugate base =
1.Draw the conjugate acid with formal charge(s) below. If there are electrons around any of the atoms ignore them for now. The details will be addressed in the next section. 2. Now specify the details of the structure that was drawn.N with three single bonds and 2 electrons around the atom in the base becomes a N atom with (blank) bonds. (Negative Charge, No Charge, Positive Charge) ,and (BLANK) electron(s) around the atom in the conjugate acid.
Organic Chemistry 1 Why did you choose your choice? Explain your reasoning and rational (theory and principles and periodic trends) as to why the species is the strongest base or the strongest conjugate acid. That is to say, provide a reasoning and an answer to your selection/choice. Why did you circle your answer for that particular species?
In box A provided draw the conjugate base for the structure below. In box B provided draw the conjugate acid for the structure below.
List the following in order from strongest base to weakest base: