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EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 2.8, Problem 37P
Fosamax (shown on the previous page) has six acidic groups. The active form of the drug, which has lost two of its acidic protons, is shown in the box. (Notice that the phosphorus atom in Fosamax and the sulphur atom in Problem 36 can be surrounded by more than eight electrons because P and S are below the second row of the periodic table.)
- a. Why are the OH groups bonded to phosphorus the strongest acids of the six groups?
- b. What of the remaining four groups is the weakest acid?
Expert Solution & Answer
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personality of each of them in terms of nucleophile vs. electrophile (some can be considered
acids/bases but we are not looking at that here). Note you may have to use your growing intuition to
figure out the personality of one of the molecules below but I believe in you! Rationalize it out
based on what we have called strong versus weak electrophiles in past mechanisms. Consider using
the memes below to help guide your understanding!
A
OH
O
B
CH3
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Molecule A: [Select]
Molecule B: [Select]
Molecule C: [Select]
Molecule D: [Select]
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H
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OH
4) Which oxygen atom in the structure below is most basic / nucleophilic? Please explain by
discussing the electron density around each oxygen atom. Show at least three resonance
structures for the compound.
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Can you show me this problem. Turn them into lewis dot structures for me please and then answer the question because I cant seem to comprehend it/ The diagrams on the picture look too small I guess.
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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