Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 10, Problem 10.27P

(a)

Interpretation Introduction

Interpretation:

The stronger base has to be determined and the structural formula of the conjugate acid has to be written.

Concept Introduction:

Electronegativity: Stronger the base, weaker its conjugate acid. When the atoms are in similar size, the stronger acid will have its hydrogen attached to the most electronegative atom.

Size affecting the stability of the base: In order to determine the strength of the base, the size of an atom overrides electronegativity. As the atoms get larger and the stability of the anions increases even though the electronegativity of the atoms decreases. Stability of the bases increases going down the group. The strongest acid will have its hydrogen attached to the largest atom. Stable bases are weak bases.

(b)

Interpretation Introduction

Interpretation:

The stronger base has to be determined and the structural formula of the conjugate acid has to be written.

Concept Introduction:

Electronegativity: Stronger the base, weaker its conjugate acid. When the atoms are in similar size, the stronger acid will have its hydrogen attached to the most electronegative atom.

(c)

Interpretation Introduction

Interpretation:

The stronger base has to be determined and the structural formula of the conjugate acid has to be written.

Concept Introduction:

Size affecting the stability of the base: In order to determine the strength of the base, the size of an atom overrides electronegativity. As the atoms get larger and the stability of the anions increases even though the electronegativity of the atoms decreases. Stability of the bases increases going down the group. The strongest acid will have its hydrogen attached to the largest atom. Stable bases are weak bases.

(d)

Interpretation Introduction

Interpretation:

The stronger base has to be determined and the structural formula of the conjugate acid has to be written.

Concept Introduction:

Size affecting the stability of the base: In order to determine the strength of the base, the size of an atom overrides electronegativity. As the atoms get larger and the stability of the anions increases even though the electronegativity of the atoms decreases. Stability of the bases increases going down the group. The strongest acid will have its hydrogen attached to the largest atom. Stable bases are weak bases.

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Chapter 10 Solutions

Organic Chemistry

Ch. 10.7 - Prob. AQCh. 10.7 - Prob. BQCh. 10.7 - Prob. CQCh. 10.7 - Prob. DQCh. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQCh. 10.7 - Prob. GQCh. 10.8 - Prob. 10.11PCh. 10.8 - Prob. AQCh. 10.8 - Prob. BQCh. 10.8 - Prob. CQCh. 10.8 - Why does nature use a reagent as complex as NAD+...Ch. 10.8 - -Hydroxyketones and -hydroxyaldehydes are also...Ch. 10.9 - Write IUPAC names for these thiols.Ch. 10 - Which are secondary alcohols?Ch. 10 - Name each compound.Ch. 10 - Prob. 10.16PCh. 10 - Name and draw structural formulas for the eight...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Arrange these compounds in order of increasing...Ch. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23PCh. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25PCh. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27PCh. 10 - In each equilibrium, label the stronger acid, the...Ch. 10 - Write equations for the reaction of 1-butanol with...Ch. 10 - Write equations for the reaction of 2-butanol with...Ch. 10 - Prob. 10.31PCh. 10 - When (R)-2-butanol is left standing in aqueous...Ch. 10 - Two diastereomeric sets of enantiomers, A/B and...Ch. 10 - Acid-catalyzed dehydration of 3-methyl-2-butanol...Ch. 10 - Show how you might bring about the following...Ch. 10 - Propose a mechanism for the following pinacol...Ch. 10 - Prob. 10.37PCh. 10 - Show how each alcohol or diol can be prepared from...Ch. 10 - Dihydropyran is synthesized by treating...Ch. 10 - Show how to convert propene to each of these...Ch. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44PCh. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46PCh. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Write the products of the following sequences of...Ch. 10 - Alcohols are important for organic synthesis,...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Using your reaction roadmap as a guide, show how...Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59P
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