Organic Chemistry - MasteringChemistry
Organic Chemistry - MasteringChemistry
8th Edition
ISBN: 9780134074665
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 2, Problem 53P

Which is a stronger base?

  1. a. HS or HO
  2. b. CH3O or CH3 N + H
  3. c. CH3OH or CH3O N +
  4. d. Cl or Br
  5. e. CH3COO or CF3COO
  6. f. CH3CHClCOO or CH3CHBrCOO

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among HS and HO has to be identified.

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.

Electronegativity:

The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

HO is the stronger base.

Explanation of Solution

If an acid lose one proton, then the formed species is a conjugated base. The stronger base is more likely to get protonated. Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base. Electronegativity increases as the size of the atom decreases. Thus, atom with small size is more basic since stability is determined by the size of the atom rather than electronegativity. Oxygen atom has least volume comparing to sulfur atom. Therefore, HO is the stronger base.

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among CH3O and CH3NH has to be identified.

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.

Electronegativity:

The chemical behavior of an atom where it attracts the shared electron pair to itself.  Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

CH3NH is the stronger base.

Explanation of Solution

If an acid lose one proton, then the formed species is a conjugated base.  The stronger base is more likely to get protonated.  Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.  Electronegativity increases as the size of the atom decreases.  Thus, atom with small size is more basic since stability is determined by the size of the atom rather than electronegativity. Nitrogen atom has least volume comparing to oxygen atom.  Therefore, CH3NH is the stronger base.

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among CH3OH and CH3O has to be identified.

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.

Electronegativity:

The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

CH3O is the stronger base.

Explanation of Solution

If an acid lose one proton, then the formed species is a conjugated base. The stronger base is more likely to get protonated. In CH3O, the negative charge is stabilizes the compound making it a strong base. Nitrogen atom has least volume comparing to oxygen atom. Therefore, CH3O is the stronger base.

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among Cl and Br has to be identified.

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.

Electronegativity:

The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

Cl is the stronger base.

Explanation of Solution

If an acid lose one proton, then the formed species is a conjugated base.  The stronger base is more likely to get protonated. Electronegativity depends on the acidity of a species.  The species having high electronegativity is the strongest base.  Electronegativity increases as the size of the atom decreases.  Thus, atom with small size is more basic since stability is determined by the size of the atom rather than electronegativity. Cl has least volume comparing to Br.  Therefore, Cl is the stronger base.

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among CH3COO and CF3COO has to be identified.

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.

Electronegativity:

The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

CH3COO is the stronger base.

Explanation of Solution

In hydrocarbons, if hydrogen atoms are replaced by electronegative atoms, it causes inductive effect due to electron withdrawing nature of electronegative atoms.  This effect stabilizes its conjugate base thus increases the strength of the acid.  The conjugated base of a weak acid is very strong.  As the electronegativity of substituent increases, the greater will be the inductive effect and so electron withdrawal of the substituent.  Thus the acid of brominated compound is weak.  Therefore, CH3COO is the stronger base.

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The stronger base among CH3ClCOO and CH3BrCOO has to be identified.

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.

Electronegativity: The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. The species having high electronegativity is the strongest base.

Answer to Problem 53P

CH3CHBrCOO is the stronger base.

Explanation of Solution

In hydrocarbon, if hydrogen atoms are replaced by electronegative atoms, it causes inductive electron withdrawal. It stabilizes its conjugate base thus increases the strength of the acid. The conjugated base of a weak acid is very strong. As the electronegativity of substituent increases, the greater will be the inductive electron withdrawal of the substituent. Electronegativity increases as the size of the atom decreases. Comparing to fluorine, chlorine is less electronegative and thus the acid of chlorinated compound is weak. Therefore, CH3CHBrCOO is the stronger base.

Conclusion

The stronger base among the following pairs was determined.

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Chapter 2 Solutions

Organic Chemistry - MasteringChemistry

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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