Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 2, Problem 2.45SP
The following compounds can all react as acids.
- a. For each compound show its conjugate base. Show any resonance forms if applicable.
- b. Rank the conjugate bases in the order you would predict from most stable to least stable.
- c. Rank the original compounds in order from strongest acid to weakest acid.
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Students have asked these similar questions
A) for each compound show its conjugate base. lone pairs have been left out.
B) rank the conjugate base in the order you would predict, from most to least stable.
C) rank the original compounds in order, from strongest to weakest acid.
A) for each compound show its conjugate base. lone pairs have been left out.
B) rank the conjugate base in the order you would predict, from most to least stable.
C) rank the original compounds in order, from strongest to weakest acid.
For the reaction given below, draw a mechanism (curved arrows) and then predict which side of the reaction is favoured under equilibrium conditions. Include lone pairs and formal charges.
Predict which side of the reaction is favored under equilibrium conditions, and explain your choice.
a. the reactants are favored, because the negative charge on the electronegative oxygen atom is more stable (making it the stronger base).
b. the products are favored, because the negative charge on the electronegative oxygen atom is more stable (making it the weaker base).
c. the products are favored, because the negative charge on the large sulfur atom is more stable (making it the weaker base).
d. the reactants are favored, because the negative charge on the large sulfur atom is more stable (making it the stronger base).
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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- 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_forward6. Rank the indicated a-H's from most to least acidic (most acidic= 1). Be sure to explain your rankings for each by drawing significant resonance structures for the conjugate base and commenting on any other factors that contribute to your rankings. H H H H. A B Cmpd Rank Resonance Structures Reasoning A Вarrow_forwardExplain why the C-H, bond is much more acidic than the C-H, bond in pentan-2-one. Select the single best answer. HH. perfar 0H, is more acidic than H, because loss of H, forms a resonance-stabilized conjugate base. H, is less acidic than H, because loss of H, forms a resonance-stabilized conjugate base. H, is more acidic than H, because loss of H, forms a resonance-stabilized conjugate base. a. H, is less acidic than H, because loss of H, forms a resonance-sta bilized conjugate base.arrow_forward
- Be sure to answer all parts. The pk of three different C-H bonds is given below. For each compound, draw the conjugate base, including all possible resonance structures for compound C. Use skeletal structures when drawing all conjugate bases. compound A H H H pK₂ = 50 Conjugate base of compound A: Conjugate base of compound B: Conjugate base of compound C: edit structure ... compound B resonance structure (negative charge on C) H H edit structure ... (one Lewis structure) edit structure ... (one resonance structure) X H pka = 43 compound C edit structure ... H H pK₂ = 19.2 resonance structure (negative charge on O) Harrow_forwardOnly typed explanation otherwise leave itarrow_forwardExplain your reasoning ?arrow_forward
- Phenol is a stronger acid than cyclohexanol. This is due to A. pi electron delocalization stabilizes phenol but not cyclohexanol. B. due to pi electron delocalization, phenol forms a more stable conjugate base. C. oxygen of phenol is partially positive due to electron delocalization so that its inductive effect enhances the positivity of the H attached to it. A and B only Band C onlyarrow_forwardB. For each set of molecules, circle the most basic molecule. Explain your choice. A. NH3 H, so more 1 audu CH₂ NaNH, 0010 2, and pop LV مازاد NHarrow_forwardAnswer the following questions about the four species A–D.a.Which two species represent a conjugate acid–base pair? b. Which two species represent resonance structures? c. Which two species represent constitutional isomers?arrow_forward
- Please answer part barrow_forward5. In each pair, which species is a stronger base? Justify your answer. Farrow_forwardWhich arrow (x, y, or z) points toward the most acidic proton in the molecule to the right? (Arrows pointing toward C can be assumed to point at the H attached to that C.) Which structural feature plays the most significant role in influencing the relative acidities of the indicated protons? a. inductive effect b. size c. resonance d. hybridizationarrow_forward
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