Organic Chemistry - With Access (Custom)
4th Edition
ISBN: 9781259147760
Author: OHIO UNIV.
Publisher: MCG
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Chapter 2, Problem 2.53P
The
a. For each compound, draw the conjugate base, including all possible resonance structures.
b. Explain the observed trend in
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3. Rank the following acids in order from strongest to weakest.HA (pKa = 2.55) H2Z (pKa1 = 4.35) H3X (pKa1 = 3.17) HY (pKa = 5.72) 4. Rank each base in order from strongest to weakest.B (pKb = 4.12) Y– (pKa = 5.72 for conjugate acid) A– (pKa = 2.55 for conjugate acid)E (pKb = 8.12)
4-Methylphenol is more acidic than ethanol (pKa 10.36 vs 16.0) , even though both contain an OH group and a methyl group. Draw the structures of the anions formed from loss of the alcoholic protons from both compounds. Use resonance to explain the difference in their respective acidities.
Given 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?
Chapter 2 Solutions
Organic Chemistry - With Access (Custom)
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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- Which base, CH3NH2 or (CH3)2NH, is the stronger base? Which conjugate acid, (CH3)2NH2+ or (CH3)2NH3+, is the stronger acid?arrow_forwardFor each equation, label the Lewis acid and the Lewis base. In addition, show all unshared pairs of electrons on the reacting atoms and use curved arrows to show the flow of electrons in each reaction. (a) F + BF3 BF4arrow_forwardWhat do you mean by carbon acid? What is the range of their pKa's?arrow_forward
- 1.95 grams of ethanolamine were dissolved in water, and the pH of the solution was adjusted with HCl until 62% of the molecules were in their protonated (conjugate acid) state. The pKa of ethanolaminium (the conjugate acid of ethanolamine) is 9.5. What is the pH of the final solution? Round your answer to one decimal place (e.g., 2.3) using standard rounding conventions for the last digit.arrow_forwardMethanoic acid (HMeth) has a Ka of 1.78 * 10-6, so what is the pOH of a 0.23 M NaMethsolution?arrow_forwardAnswer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: phenol (pKa = 9.9), and acetic acid (pKa = 4.8). 1.) - The stronger acid is - Its conjugate base is - The species that predominate at equilibrium are 2.) - The stronger base is - Its conjugate acid is - The species that predominate at equilibrium arearrow_forward
- What is the K a of an acid whose pK a is 8.60?arrow_forwardAnswer questions a-c about the Bronsted acid-base reaction below using the identifying letters A-D below each structure. The pKa's for the acids of interest are: water (pKa = 15.7), and phenol (pKa = 9.9).a) The stronger base is b) Its conjugate acid is c) The species that predominate at equilibrium are (two letters, e.g. ac)arrow_forwardDefine why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an alpha carbon of an ester? What are their pKa's?arrow_forward
- Consider the following reaction: X-SH ⇌ X-S- + H+ The pKa for the sulfhydryl (thiol) group (SH) is 8.37. Choose any/all statements that apply: X-SH is a base. X-S- is the conjugate base of X-SH. H+ is a proton acceptor. X-S- is the conjugate acid of X-SH. At neutral pH, the equilibrium lies such that X-S- is the predominant species.arrow_forwardUsing pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forwardThe pKa of three CH bonds is given below.a.For each compound, draw the conjugate base, including all possible resonance structures. b. Explain the observed trend in pKaarrow_forward
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