Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 2.9, Problem 35P
Using the table of pKa values given in Appendix I, answer the following:
- a. Which is the most acidic organic compound in the table?
- b. Which is the least acidic organic compound in the table?
- c. Which is the most acidic
carboxylic acid in the table? - d. Which is more electronegative: an sp3 oxygen or an sp2 oxygen? (Hint: Pick a compound in Appendix I with a hydrogen attached to an sp2 oxygen and one with a hydrogen attached to an sp3 oxygen and compare their pKa values.)
- e. Which compounds demons that the relative electronegativities of a hybridized nitrogen atom are sp > sp2 > sp3?
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Using the table of pKa values given in Appendix I, answer the following: a. Which is the most acidic organic compound in the table? b. Which is the least acidic organic compound in the table? c. Which is the most acidic carboxylic acid in the table? d. Which is more electronegative: an sp3 oxygen or an sp2 oxygen? (Hint: Pick a compound in Appendix I with a hydrogen attached to an sp2 oxygen and one with a hydrogen attached to an sp3 oxygen and compare their pKa values.) e. Which compounds demonstrate that the relative electronegativities of a hybridized nitrogen atom are sp 7 sp2 7 sp3?
F
Below are four molecules that are pH sensitive:
F
O
Structure A
OH
F
O
Structure
OH
Br
O
Br
Structure C
1. Sort the given molecules in the increasing of pka values.
OH
2. What was your choice for strongest acid? Explain your answer.
Br
Br
Structure D
OH
what is the pKa of the conjugate acid of the molecules below?
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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- Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)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_forwardonly TYPED ANSWER PLZarrow_forward
- 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_forwardWhich acid do you think would have the lower pKa value: HBrO4, HBrO3, HBrO2, or HBrO? Explain your answer.arrow_forwardWhich species is the conjugate acid of ammonia, NH3? Select one: O a. HẠN O b. H3N* О с. НN O d. HẠN* Which compound has the lowest pk,? Select one: O a. H2O O b. H2S NH3 O d. CH4 Which compound is the strongest acid? CH4 CH,CH3 H2C=CH2 HCECH II IV Select one: O a. Ob. О с. II O d. IVarrow_forward
- The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74). Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_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_forwardCarnosine, found in muscle and brain tissue, acts as a buffer to neutralize small amounts of acid. The pKa of the conjugate acid of carnosine is close to 7.0. What is its structure?arrow_forward
- If compound A has a ka of 3.0 x 10-11 , compound B has a ka of 1.1 x 10-10 and compound C has a ka of 1.8 x 10-5, which compound is the weakest acid?arrow_forward6. Morphine (structure shown) is a prescription-strength analgesic used to treat severe pain. pKa = 9.90 > HO. pKb = 8.20 HO" a) At the pH of human blood plasma (pH 7.4), what is the charge on the -OH group (with pKa = 9.90)? Circle one: positive neutral negative b) At the pH of human blood plasma (pH 7.4), what is the charge on the amino group (with pkb = 8.20)? Circle one: positive neutral negative c) At what pH would morphine be the least polar: pH 4.0, 7.0, or 11.0? Circle one: 4.0 7.0 11.0 Briefly explain:arrow_forwardArrange these acids according to their expected pKa values. Highest pKa Lowest pKa CICH,CH,COOH CH;CH,COOH C,CHCOOH CICH,COOHarrow_forward
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