7th Edition

ISBN: 9780321803221

Author: Paula Y. Bruice

Publisher: Prentice Hall

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Textbook Question

Chapter 2.10, Problem 39P

A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. The pK_a, values of the two groups are shown.

Chapter 2.10, Problem 39P, A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group

a. If the pK_a value of a carboxylic add such as acetic acid is about 5 (see Table 2.1 ), then why is the pK_a value of the carboxylic acid group of alanine so much lower?
b. Draw the structure of alanine in a solution at pH = 0.
c. Draw the structure of alanine in a solution at physiological pH (pH 7.4).
d. Draw the structure of alanine in a solution at pH = 12.
e. Is there a pH at which alanine is uncharged (that is. neither group has a charge)?
f. At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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Chapter 2.10, Problem 37P

Chapter 2.10, Problem 41P

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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. 6P Ch. 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. 14P Ch. 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. 22P 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 - Prob. 27P Ch. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Prob. 29P Ch. 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. 34P Ch. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - Prob. 36P Ch. 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. 51P Ch. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 54P Ch. 2 - Prob. 55P Ch. 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. 63P Ch. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 65P Ch. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 68P Ch. 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. 1P Ch. 2 - Prob. 2P Ch. 2 - Prob. 3P Ch. 2 - Which of the reactions in Problem 3 favor...Ch. 2 - Prob. 5P Ch. 2 - Prob. 6P Ch. 2 - Prob. 7P Ch. 2 - Which is the stronger acid? a. ClCH2CH2OH or...Ch. 2 - Prob. 9P Ch. 2 - Prob. 10P Ch. 2 - Which is a more stable base? Remembering that the...Ch. 2 - Which is the Stronger acid?Ch. 2 - Prob. 13P Ch. 2 - a. Draw the structure of (CH3COOH (pKa = 4.7) at...

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Solution Summary: The author explains the Henderson-Hasselbalch equation for the pK_a value of COOH group of alanine.

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