Concept explainers
(a)
Interpretation:
Out of the given pair of molecules, the stronger acid is to be predicted.
Concept introduction:
Within acids with similar structures, the strength of each acid depends on the presence of electronegative atoms. The more the electronegativity and number of such atoms, the greater the charge stability and therefore higher the strength.
(b)
Interpretation:
Out of the given pair of molecules, the stronger acid is to be predicted.
Concept introduction:
In acids with the acidic proton attached to the same atom, with the same hybridization, the charge stability depends on the delocalization of the charge in the anion formed on dissociation. Greater the delocalization, i.e., the more the number of atoms over which the charge is spread, greater the stability of the anion (conjugate base) and greater the strength of the acid.
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- 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).arrow_forwardComplete 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_forwardThe 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.arrow_forward
- Construct an explanation for why sulfuric acid is such a strong acid. (Note that sulfur is in thethird row of the periodic table and can have more than eight electrons.)arrow_forwardRank the following compounds according to acidity, 1 being the most acidic and 4 being the least acidic. First, list the ranking number followed by the compound letter in order from 1 to 4, and then explain your reasoning in a sentence or two.arrow_forwardDraw the most stable conjugate base of this molecule. Briefly explain your choice in thespace provided.arrow_forward
- For the following molecules, identify the acidic hydrogens from among those that are bolded. For each acidic hydrogen that you identify, draw the conjugate base that results from a base removing that acidic hydrogen. For molecules with more than one acidic hydrogen, draw a separate conjugate base for each one.arrow_forwardWhich compound, M or N, is the stronger acid? Explain your choice.arrow_forwardPut a 1 under the most basic molecule, a 2 under the second most basic molecule, and a 3 under the least basic molecule in each set of three molecules. Choose a set and give your reasoning for your answer.arrow_forward
- In equilibrium, label the stronger acid, the stronger base, the weaker acid, and the weaker base. Also estimate the position of equilibrium.arrow_forwardFor each pair of bases, identify the stronger base.arrow_forwardDecide which compound is the acid and which is the base, and draw the products of each proton transfer reaction.arrow_forward
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