Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 2, Problem 50P
Interpretation Introduction
Interpretation:
Among the two buffers protonated methylamine/methylamine buffer and protonated ethylamine/ethylamine buffer the buffer which is better to carry out a reaction that produces protons has to be determined.
Concept Introduction:
Important formulas regarding acid-base concepts are:
Henderson-Hasselbalch equation
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You are planning to carry out a reaction that produces protons. The reaction will be buffered at pH = 10.5. Would it be better to use a protonated methylamine/methylamine buffer or a protonated ethylamine/ethylamine buffer? (pKa of protonated methylamine = 10.7; pKa of protonated ethylamine = 11.0)
hydrogens on a carbon adjacent to a carbonyl group are far
more acidic than those not adjacent to a carbonyl group. The anion derived from acetone,
for example, is more stable than is the anion derived from ethane. Account for the greater
stability of the anion from acetone.
CH,ČCH, H
CH,CH, H
Acetone
Ethane
pK, 20.2
pK, 51
For each value of Ka, calculate the corresponding value of pKa. Which compound is the stronger acid?
Q.) chloroacetic acid, Ka = 1.38 X 10-3
Chapter 2 Solutions
Essential Organic Chemistry, Global Edition
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Draw the products of the acidbase reaction when a....Ch. 2.1 - a.What is the conjugate acid of each of the...Ch. 2.2 - a. Which is a stronger acid, one with a pKa of 5.2...Ch. 2.2 - Prob. 5PCh. 2.2 - Antacids are compounds that neutralize stomach...Ch. 2.2 - Are the following body fluids acidic or basic? a....Ch. 2.3 - Draw the conjugate acid of each of the following:...Ch. 2.3 - a. Write an equation showing CH3OH reacting as an...Ch. 2.3 - Prob. 10P
Ch. 2.3 - a. Which is a stronger base, CH3COO or HCOO? (The...Ch. 2.3 - Using the pKa values in Section 2.3, rank the...Ch. 2.4 - Prob. 13PCh. 2.5 - Prob. 14PCh. 2.5 - Ethyne has a pKa value of 25, water has a pKa...Ch. 2.5 - Which of the following bases can remove a proton...Ch. 2.6 - List the ions (CH3, NH2, HO, and F) in order from...Ch. 2.6 - List the carbanions shown in the margin in order...Ch. 2.6 - Which is a stronger acid?Ch. 2.6 - a. Draw the products of the following reactions: A...Ch. 2.6 - List the halide ions (F, Cl, Br, and I) in order...Ch. 2.6 - a. Which is more electronegative, oxygen or...Ch. 2.6 - Which is a stronger acid? a. HCl or HBr b....Ch. 2.6 - a. Which of the halide ions (F, Cl, Br, and I) is...Ch. 2.6 - Which is a stronger base? a. H2O or HO b. H2O or...Ch. 2.7 - Which is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Which is a stronger base?Ch. 2.8 - Fosamax has six acidic groups. The structure of...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.10 - For each of the following compounds (shown in...Ch. 2.10 - Prob. 33PCh. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.11 - What products are formed when each of the...Ch. 2 - a. List the following alcohols in order from...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - Prob. 40PCh. 2 - a. List the following carboxylic acids in order...Ch. 2 - For the following compound, a. draw its conjugate...Ch. 2 - List the following compounds in order from...Ch. 2 - For each of the following compounds, draw the form...Ch. 2 - Give the products of the following acidbase...Ch. 2 - Prob. 46PCh. 2 - For each compound, indicate the atom that is most...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which acids can HO remove a proton in a...Ch. 2 - Prob. 50PCh. 2 - Which is a stronger acid? a. CH29CHCOOH or...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Draw the products of the following acidbase...Ch. 2 - Prob. 4PCh. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Prob. 8PCh. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Prob. 11PCh. 2 - Prob. 12PCh. 2 - Prob. 13PCh. 2 - Prob. 14P
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- Will acetylene react with sodium hydride according to the following equation to form a salt and hydrogen, H2? Using pKa values given in Table 4.1, calculate Keq for this equilibrium.arrow_forwardNaHCO3 can deprotonate benzoic acid but cannot deprotonate phenol. On the other hand, NaOH can deprotonate both benzoic acid and phenol. Given this information, rank the molecules numbered I to V in order of decreasing acidity. COH cOH он H,0 H,CO, IV CH3 II I II (A) V > II >I > III > IV (В) II > 1 > V > III IV (C) II > V >I > IV > IIarrow_forwardThe ammonium ion (pKa = 9.25) has a lower pKa than the methyl ammonium ion (pKa = 10.66). Explain which of the two species is the stronger basearrow_forward
- Verify that the equilibrium position for the reaction between phenol and hydroxide ion is on the right by comparing the pKa value of the acid on the left with that of the acid on the right. Which acid is stronger? do the same for the reaction of phenol with hydrogen carbonate ionarrow_forwardWhat is the predominant form of A–A–A at pH = 1?arrow_forwardThe correct order of increasing the acidity for the following molecules is: 1,3-Diketone > carboxylic acid > alcohol > ketone > amide (the weakest) Carboxylic acid >1,3-diketone > ketone > alcohol > nitrile (the weakest) 1,3-Diketone > 1,3-diester > alcohol > ketone > amide (the weakest) الأنتنامى 1,3-Diketone > ketone > alcohol > 1,3-diester > amide (the weakest) Carboxylic acid >1,3-diketone > nitrile > alcohol > ketone (the weakest)arrow_forward
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- What is the pOH of:(a) a 0.0100 F solution of phtalic acid?(b) a 0.0100 F solution of monopotassium phtalate? (c) a 0.0100 F solution of dipotassium phtalate?if pKa1 = 2.950 and pKa2 = 5.408 for phtalic acidarrow_forwardAnother way to express acid strength is by using pk b:pK a =−logK a Another way to express base strength is by using pK b pK b =−logK b A new potential heart medicine, code-named X-281, is being tested by a pharmaceutical company, Pharma-pill. As a research technician at Pharma-pill, you are told that X-281 is a monoprotic weak acid, but because of security concerns, the actual chemical formula must remain top secret. The company is interested in the drug's K a value because only the dissociated form of the chemical is active in preventing cholesterol buildup in arteries.To find the pK a of X-281, you prepare a 0.079 M M test solution of X-281 at 25.0 ∘ C The pH of the solution is determined to be 3.00. What is the pK a of X-281?arrow_forwardThe C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3Darrow_forward
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