Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 2.2, Problem 4P
a. Which is a stronger acid: one with a pKa of 5.2 or one with a pKa of 5.8?
b. Which is a stronger acid: one with an acid dissociation constant of 3.4 × 10–3 or one with an acid dissociation constant of 2.1 × 10–4?
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Which species is the conjugate acid of ammonia, NH3?
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O a. HẠN
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О с. НN
O d. HẠN*
Which compound has the lowest pk,?
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O a. H2O
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NH3
O d. CH4
Which compound is the strongest acid?
CH4
CH,CH3
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a. Which of the acids in the table above has the strongest conjugate base?
b. What is the structure of the strongest acid in the table above?
Using 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.
Chapter 2 Solutions
Organic Chemistry
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Draw the products of the addbase renc1 ion when a....Ch. 2.1 - a. What is the conjugate acid of each or the...Ch. 2.2 - a. Which is a stronger acid: one with a pKa of 5.2...Ch. 2.2 - An acid has a Ka of 4.53 106 in water. What is...Ch. 2.2 - Prob. 6PCh. 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 - Estimate the pKa values of the following...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. 14PCh. 2.5 - a. For each of the acid-base reactions in Section...Ch. 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. 2.5 - Calculate the equilibrium constant for the...Ch. 2.6 - Rank the ions (CH3, NH2, HO, and F) from most...Ch. 2.6 - Rank the carbanions shown in the margin from most...Ch. 2.6 - Which is the stronger acid?Ch. 2.6 - Prob. 22PCh. 2.6 - Rank the halide ions (F, Cl, Br, and l) from...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 l) is...Ch. 2.6 - Prob. 27PCh. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Prob. 29PCh. 2.7 - What is a stronger base?Ch. 2.8 - Fosamax (shown on the previous page) has six...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.8 - Prob. 34PCh. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - Prob. 36PCh. 2.10 - As long as the pH is not less than _______, at...Ch. 2.10 - A naturally occurring amino acid such as alanine...Ch. 2.10 - For each of the following compounds, indicate the...Ch. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.12 - Draw the products of the following react ions. Use...Ch. 2.12 - What product are formed when each of the following...Ch. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - According to the explanations by Lewis, if a...Ch. 2 - a. Rank the following carboxylic acids from...Ch. 2 - Prob. 51PCh. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - For each compound, indicate the atom that is most...Ch. 2 - a. Given the Ka values, estimate the pKa value of...Ch. 2 - A single bond between two carbons with different...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which of the following compounds can HO...Ch. 2 - a. For each of the following pairs of reactions,...Ch. 2 - Prob. 63PCh. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 65PCh. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 68PCh. 2 - a. If an add with a pKa of 5.3 is in an aqueous...Ch. 2 - Calculate the pH values of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Prob. 3PCh. 2 - Which of the reactions in Problem 3 favor...Ch. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Which is the stronger acid? a. ClCH2CH2OH or...Ch. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Which is a more stable base? Remembering that the...Ch. 2 - Which is the Stronger acid?Ch. 2 - Prob. 13PCh. 2 - a. Draw the structure of (CH3COOH (pKa = 4.7) at...
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- Which compound in each pair is the stronger acid? (See the Attachment)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_forwardI know that the 3rd one (second on the right side) has the highest pka because it's an alcohol and an alcohol is less acidic than a phenol. but I don't understand which compound has the lowest pka (strongest acid)?arrow_forward
- Chemistry 19. Draw the products of each reaction. using pka values decide if the equilibrium favors reactants or products. a) F3 C GH OH + OCH₂CH3 Conj.base Pka = 0.2 Conj acid (pka=16) b) [JOH+ тон + мансоз pka = 10 Conj.aud (Pka = 15-7) c) H3C NH₂ + H₂SO4 Pka = -9 .t- d) H-CEC-H+ Lí CH2CH3 pka=25 Conj. acid (pka = 10.7) Conj. aud (pka=50) Conj. base Conj. base + CO₂ Conj. basearrow_forwardOrganic Chemistry help! Which compound has the conjugated base with higher pKa and why?arrow_forwardThe pKa for Molecule A is 10 units lower than Molecule B. Molecule A Draw conjugate base of A :B H H pKa = 10 Molecule B Draw conjugate base of B OCH3 :B H H pКa 3 20 Please provide a brief explanation for the difference in pKa of these to molecules.arrow_forward
- Rank the compounds or ions in order of increasing acidity (or decreasing p?a).arrow_forwardThe higher the pK, value the weaker the acid. True Falsearrow_forwardA ka of weak acid is 1 E-6, this means that For 1 million unionized acid, there is just one molecule is ionized .a O The concentration of hydronium ion equals the square root of its pKa value .b O For 1 million ionized acid, there is just one molecule is unionized .c O The concentration of hydroxyl ion equals the square root of its pka value .d Oarrow_forward
- The 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_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_forwardArrange the compounds in order of increasing base strength. Consult the table for the pK, values of each conjugate acid pK, values of conjugate acids. a. Acid pKa Acid pKa CH3 CH3 51 H3PO, 2.1 H2 35 HNOS -1.5 H2O 15.7 H3O+ -1.74 H2CO3 10.33 H2SO4-5.2 H2S 7.04 HBr -8 C6 H5 COOH 4.19 (Suppose the strongest base is b, the base of intermediate strength is c, and the weakest base is a. Then this leads to the follow C H5 COO H2PO4 H aarrow_forward
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