Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 2, Problem 2.41SP
The following compounds are listed in increasing order of acidity. In each case, the most acidic proton is shown in red.
- a. Show the structure of the conjugate base of each acid, including any resonance forms.
- b. Explain why X is a stronger acid than W.
- c. Explain why Y is a stronger acid than X.
- d. Explain why Z is a stronger acid than Y.
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2. Which structure is the stronger acid, A or B? Explain your answer.
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A
Which of the following compounds is the stronger
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or
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v is more electronegative than
and will
v more electron density
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Thus, the nitrogen atom in NCI3 has a
v positive charge than it does in NH3.
The
v positive charge means that is
v difficult to add H* to NCI3 than it is to
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Hc.
NHa
Chapter 2 Solutions
Organic Chemistry (9th Edition)
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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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.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_forwardPhenol (shown below) has a pKa10 . a. Based on pKa data, is phenol a stronger or weaker acid than an ordinaryalcohol (e.g.. CH3OH ) or water? b. Draw the conjugate base of phenol (called phenoxide) including allimportant resonance structures. c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. (You may want to consider first why phenoxide is lowerin PE than methoxide (RO) or hydroxide (HO) .arrow_forward
- Consider the following bases: a. For each base above, circle the atom/atoms with the highest PE (will release the most P.E.when a lone pair on this atom combines with an H+ ) b. Rank the bases 1 (highest P.E./strongest base) to 7 (lowest PE/weakest base), and explainyour reasoning.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_forwardComplete each Lewis structure, draw all important resonance structures, predict a value for thebond angles requested, and explain your reasoning. a. Nitrous acid (HNO2)HONOHON=ONO= b. Enolate ion (C2H3O) HC1C2=HC2C1=arrow_forward
- 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 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_forwardLabel all of the acidic hydrogen. (Do not count any of the ones that are not shown) bns 2001320 Circle the one that is the most acidic kne noltamoino siano ws Explain, using CARDIO, why it is the most acidic. H H H H N. H. H H stasib was baie vincul CI 6057 enim09 ogmo) ons nod:6) istim relev H S WH bus il basi WH Uns 2506 A toarrow_forward
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