Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 2, Problem 54P

(a)

Interpretation Introduction

Interpretation:

The predominant form of the compound CH3COOH that exist at pH=3,6,10,14 has to be drawn.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Henderson-Hasselbalch equation explains the relationship between pH of solution and pKa of acid. For a dissociation of acid (HA) in aqueous solution,

HA+H2OH3O++A

pKa=pH+log[HA][A]

During a dissociation of acid in aqueous solution,

  • If pH=pKa, the concentration of compound in its acidic and basic form is equal.
  • If pH<pKa, the compound exist in its acidic form.
  • If pH>pKa, the compound exist in its basic form.

(b)

Interpretation Introduction

Interpretation: The predominant form of the compound CH3CH2N+H3 that exist at pH=3,6,10,14 has to be drawn.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Henderson-Hasselbalch equation explains the relationship between pH of solution and pKa of acid. For a dissociation of acid (HA) in aqueous solution,

HA+H2OH3O++A

pKa=pH+log[HA][A]

During a dissociation of acid in aqueous solution,

  • If pH=pKa, the concentration of compound in its acidic and basic form is equal.
  • If pH<pKa, the compound exist in its acidic form.
  • If pH>pKa, the compound exist in its basic form.

(c)

Interpretation Introduction

Interpretation:

The predominant form of the compound CF3CH2OH that exist at pH=3,6,10,14 has to be drawn.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Henderson-Hasselbalch equation explains the relationship between pH of solution and pKa of acid. For a dissociation of acid (HA) in aqueous solution,

HA+H2OH3O++A

pKa=pH+log[HA][A]

During a dissociation of acid in aqueous solution,

  • If pH=pKa, the concentration of compound in its acidic and basic form is equal.
  • If pH<pKa, the compound exist in its acidic form.
  • If pH>pKa, the compound exist in its basic form.

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Chapter 2 Solutions

Organic Chemistry

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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