Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 2.3, Problem 12P
Estimate the pKa values of the following compounds:
a. CH3CH2CH2NH2
b. CH3CH2CH2OH
c. CH3CH2COOH
d. CH3CH2CH2
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Consider compounds 1 and 2 in the image and select the correct statement.
N.
Qo30
N.
N
1
فيه
N
IZ
ZI
2
O a.
The TPSA of compound 1 is the same as the TPSA of compound 2
O b. The TPSA of compound 1 is lower than the TPSA of compound 2
O c. The TPSA of compound 1 is higher than the TPSA of compound 2
Part B
Benzoic acid is a weak acid that has antimicrobial properties. Its sodium salt, sodium benzoate, is a preservative found
in foods, medications, and personal hygiene products. Benzoic acid dissociates in water:
C6H5 COOH(aq) + H₂O(1) C6H5COO- (aq) + H3O+ (aq)
-1
The pK₂ of this reaction is 4.2. In a 0.66 mol L-¹ solution of benzoic acid, what percentage of the molecules are
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Pregabalin, C3H17NO2 is used as a treatment of epilepsy and neuropathic pain.
NH2
pK, = 4.2
%3D
H.
pK =
HO,
= 3.4
Select the equilibrium corresponding the to the pK, = 9.8
CgH18NO2 (aq) + H20 (I) C3H17NO2 (aq) + OH (aq)
C3H16NO2 (aq) + H20 (1) CgH17NO2 (aq) + OH (aq)
CgH17NO2 (aq) + H20 (1) C3H18NO2 *(aq) + OH (aq)
C3H17NO2 (aq) + H20 (1) CgH16NO2 (aq)+ H30*(aq)
Chapter 2 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
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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