EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 2, Problem 14P
a. Draw the structure of (CH3COOH (pKa = 4.7) at pH = 2, pH = 7, and pH = 10.
b. Draw the structure of (CH3OH (pKa = 15.5) at pH = 2, pH = 7, and pH = 10.
c. Draw the structure of (CH3
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Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 2 Solutions
EBK ORGANIC CHEMISTRY
Ch. 2.1 - Which of the following are not acids? CH3COOH CO2...Ch. 2.1 - Consider the following reaction: a. What is the...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. 7PCh. 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. 15PCh. 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. 23PCh. 2.6 - What reaction in Problem 23 has the smallest...Ch. 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 - Which is a stronger base? (The potential maps in...Ch. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Rank the following compounds from strongest add to...Ch. 2.7 - What is a stronger base?Ch. 2.8 - For each of the following compounds, indicate the...Ch. 2.8 - Prob. 35PCh. 2.8 - Which is a stronger acid? Why?Ch. 2.8 - Fosamax (shown on the previous page) has six...Ch. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - For each of the following compounds (here shown in...Ch. 2.10 - As long as the pH is not less than _______, at...Ch. 2.10 - a. Indicate whether a protonated amine (RN+H3)...Ch. 2.10 - A naturally occurring amino acid such as alanine...Ch. 2.10 - a. At what pH is the concentration of a compound,...Ch. 2.10 - For each of the following compounds, indicate the...Ch. 2.10 - Given the data in Problem 47: a. What pH would you...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 - 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 alcohols from strongest to...Ch. 2 - a. Rank the following carboxylic acids from...Ch. 2 - Prob. 57PCh. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 60PCh. 2 - Prob. 61PCh. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - A single bond between two carbons with different...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 - 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. 69PCh. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 71PCh. 2 - Prob. 72PCh. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 75PCh. 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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