Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 2.11, Problem 2.15P
(a)
Interpretation Introduction
To determine: The reactions of the given compounds with water.
Interpretation: The reactions of the given compounds with water are to be stated.
Concept introduction: When an acid donates a proton, the species formed is known as conjugate base and when the base accepts a proton, the species formed is known as conjugate acid.
(b)
Interpretation Introduction
To determine: The corresponding
Interpretation: The
Concept introduction: The equilibrium constant of an acid dissociation reaction depends on the strength of an acid involved in the reaction. The
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The acidity of compounds will be effected by ____.
select all that are correct
Select one or more:
a.Whether R or S centres are present in the molecule
b. The ability of the conjugate base to distribute charge
c. The electronegativity of groups at position nearby to the proton donor group
d. Temperature
e. Neighbouring electropositive groups
Which acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.
Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.
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 ammonium ion (NH4 +, pKa = 9.25), has a lower pKa than the methylammonium ion (CH3NH3 +, pKa = 10.66) Which is the stronger base, ammonia (NH3) or methylamine (CH3NH2) ? Explainarrow_forwardHow would the pKa values of carboxylicacids, alcohols, ammonium ions 1RNH32 + , phenol, and an anilinium ion 1C6H5NH32 + change if they were determined in a solvent less polar than water?arrow_forwardGiven that the Ka value for acetic acid is 1.8 × 10−5 and the Ka value for hypochlorousacid is 3.5 × 10−8, which is the stronger base, OCl− or C2H3O2−?arrow_forward
- Calculate the pKa of each acid and indicate which is the stronger acid. C6O2H8, Ka = 1.7 x 10–5 C2O4H2, Ka = 5.9 x 10–2arrow_forwardexplain in great detail why the pKa values are what they are and compare them among the three compounds. The conjugate acids that are protonated are drawn in red for each compound. Which one based on the pKa is most acidic and what does that tell you about how basic their lone pairs are?arrow_forwardPhthalic acid and isophthalic acid have protons on two carboxy groupsthat can be removed with base. (a) Explain why the pKa for loss of thefirst proton (pKa1) is lower for phthalic acid than isophthalic acid. (b)Explain why the pKa for loss of the second proton (pKa2) is higher forphthalic acid than isophthalic acid.arrow_forward
- The Ka of acetic acid (CH3CO2H) is 1.8x10-5 and the Kb of methylamine (CH3NH2) is 4.4x10-4. Complete the following equilibrium reaction (acid-base reaction) equation and predict the side of the equilibrium that is favored. Explain. Show all your work.arrow_forwardWhich of the following reactions favor formation of the products? (For the pKa values necessary to solve this problem, see Appendix I. Recall that the equilibrium favors formation of the weaker acidarrow_forwardWhat steps would you need to take to calculate the pKa1 and pKa2 of something? For example: hydrosulfuric acid H2S(aq) (-38.6 ΔH^0 f kJ mol^-1).arrow_forward
- Thiocyanic acid (HSCN) is an inorganic acid (pKa = 1.1 at 25 °C) that can be classified as “strong” largely due to resonance stabilization of its conjugate base, thiocyanate (SCN– ). In the space provided below, draw Lewis electron dot structures of SCN- and all of its important resonance forms.arrow_forwardWhat do you mean by carbon acid? What is the range of their pKa's?arrow_forwardDicarboxylic acids have two dissociation constants, one for the initial dissociation into a monoanion and one for the second dissociation into a dianion. For oxalic acid, HO2C—CO2H, the first ionization constant is pKal = 1.2 and the second ionization constant is pKa2 = 4.2. Why is the second carboxyl group far less acidic than the first?arrow_forward
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