Organic Chemistry (Loose) -With Access
7th Edition
ISBN: 9780321933805
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 2.10, Problem 37P
As long as the pH is not less than _______, at least 50% of a protonated
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In the gas phase the base strength of amines increases along theseries:NH3 < CH3NH2 < (CH3)2NH < (CH3)3NDiscuss the effects determining this order
For the following molecule, draw the major species at each pH. The carboxylic acid is drawn as a conjugate acid and the amine are drawn as the conjugate base.
1. pH of 2
2. pH of 4
3. pH of 7
Which of the ff statements is false?
In aqueous solution the order of base strength R3N > R2NH > RNH2 > NH3.
Alkyl groups increase the electron density on nitrogen, making the amine more basic.
Alkyl groups stabilize the positive charge on the conjugate acid making the ammonium ion less acidic.
Solvation through H-bonding with water is more important in the conjugate acid than in the free amine.
Chapter 2 Solutions
Organic Chemistry (Loose) -With Access
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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- An unknown compound, X, is thought to have a carboxyl group with a p?a of 2.5 and a second ionizable group with a p?a between 5.0 and 8.0. When 50.0 mL of 0.2 M NaOH is added to 75.0 mL of a 0.2 M solution of X at pH 2.5, the pH increases to 7.13. Calculate the p?a of the second ionizable group of X.arrow_forwardWhat fraction of iminodiacetic acid is in each of its four forms (H3AH3A H2A−H2A−, HA2−HA2−, A3−A3−) at pH 3.519? The p?apKa values for iminodiacetic acid are 1.85 (p?a1pKa1), 2.84 (p?a2pKa2) and 9.79 (p?a3pKa3).arrow_forwardTrue or false Acidic drugs tend to ionize in basic medium. Basic drugs tend to be absorbed in basic environment, like the duodenum. Acidic drugs are excreted faster if the urine is acidic. Basic drugs remain unionize in a basic environment. Polarity of the drug increases as the number of carbon increases in a compound.arrow_forward
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- Explain the effect of acid on the solubility of the water-insoluble amines. do not copy from google, i will downvotearrow_forwardGive proper explanation of the correct option and proper explanation of the incorrect options. No answer from chat gpt will dislike keep in mind.arrow_forward8) An available treatment for severe tension headache is Fioricet 3 which contains butalbital-acetaminophen-caffeine-codeine. Propose a liquid-liquid extraction plan to separate all 4 components Butalbital pKa = 8.48 (weak acid) Acetaminophen pKa = 9.46 (phenol; the amide is not easily protonated) Caffeine pKa = 14 (assume neutral at any practical pH) Codeine pKa = 8.2 (amine).arrow_forward
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