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 10.21P

(a)

Interpretation Introduction

Interpretation:

The solvent with greater solubility in water has to be selected.

Concept Introduction:

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Solubility: Interaction of polar compound with water occurs by hydrogen bonding formation between compounds and water.

Hydrogen-bond donors: The hydrogen atom that is attached to the high electronegative atom participates in hydrogen bond. Thus, that Hydrogen atom is known as hydrogen-bond donors.

Hydrogen-bond acceptor: The atom (high electronegative atom with lone pairs) to which the hydrogen atom is participated in hydrogen bond.

(b)

Interpretation Introduction

Interpretation:

The solvent with greater solubility in water has to be selected.

Concept Introduction:

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Solubility: Interaction of polar compound with water occurs by hydrogen bonding formation between compounds and water.

Hydrogen-bond donors: The hydrogen atom that is attached to the high electronegative atom participates in hydrogen bond. Thus, that Hydrogen atom is known as hydrogen-bond donors.

Hydrogen-bond acceptor: The atom (high electronegative atom with lone pairs) to which the hydrogen atom is participated in hydrogen bond.

(c)

Interpretation Introduction

Interpretation:

The solvent with greater solubility in water has to be selected.

Concept Introduction:

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Solubility: Interaction of polar compound with water occurs by hydrogen bonding formation between compounds and water.

Hydrogen-bond donors: The hydrogen atom that is attached to the high electronegative atom participates in hydrogen bond. Thus, that Hydrogen atom is known as hydrogen-bond donors.

Hydrogen-bond acceptor: The atom (high electronegative atom with lone pairs) to which the hydrogen atom is participated in hydrogen bond.

(d)

Interpretation Introduction

Interpretation:

The solvent with greater solubility in water has to be selected.

Concept Introduction:

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Solubility: Interaction of polar compound with water occurs by hydrogen bonding formation between compounds and water.

Hydrogen-bond donors: The hydrogen atom that is attached to the high electronegative atom participates in hydrogen bond. Thus, that Hydrogen atom is known as hydrogen-bond donors.

Hydrogen-bond acceptor: The atom (high electronegative atom with lone pairs) to which the hydrogen atom is participated in hydrogen bond.

(e)

Interpretation Introduction

Interpretation:

The solvent with greater solubility in water has to be selected.

Concept Introduction:

Hydrogen bonding: The attractive interactions between hydrogen atom bonded to an atom of high electronegativity (most commonly O or N) and a lone pair of electrons on another atom of electrons on another atom of high electronegativity (again, most commonly O or N).

Solubility: Interaction of polar compound with water occurs by hydrogen bonding formation between compounds and water.

Hydrogen-bond donors: The hydrogen atom that is attached to the high electronegative atom participates in hydrogen bond. Thus, that Hydrogen atom is known as hydrogen-bond donors.

Hydrogen-bond acceptor: The atom (high electronegative atom with lone pairs) to which the hydrogen atom is participated in hydrogen bond.

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(ii) Name the following using IUPAC system of nomenclature:   (a) CH2 (Cl) CH (NH2) CHO       (b) CH3 C (Br) CH2 CH (F) COOH                            Br
Write the reagent or draw structures of the starting material or organic product(s) in the following reactions. If more than one product is formed, identify the major product where possible. (a) (b) HO OH OH H2SO4 ? Cl₂ ? FeCl3
(b) NABH, CH3 COCH,CH3 CH3CH2OH (c)

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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