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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Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compound…

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Textbook Question

Chapter 10, Problem 10.43P

The tosylate of a primary alcohol normally undergoes an S_N2 reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula C₇H₁₂O.

Chapter 10, Problem 10.43P, The tosylate of a primary alcohol normally undergoes an SN2 reaction with hydroxide ion to give a

Propose a structural formula for this compound and a mechanism for its formation.

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Chapter 10 Solutions

Organic Chemistry

Ch. 10.1 - Write IUPAC names for these alcohols and include...Ch. 10.1 - Classify each alcohol as primary, secondary, or...Ch. 10.1 - Write IUPAC names for these unsaturated alcohols.Ch. 10.2 - Arrange these compounds in order of increasing...Ch. 10.2 - Prob. 10.5P Ch. 10.4 - Predict the position of equilibrium for this...Ch. 10.5 - Show how to convert (R)-2-pentanol to...Ch. 10.6 - Draw structural formulas for the alkenes formed by...Ch. 10.6 - Propose a mechanism to account for this...Ch. 10.7 - Propose a mechanism to account for the following...

Ch. 10.7 - Prob. AQ Ch. 10.7 - Prob. BQ Ch. 10.7 - Prob. CQ Ch. 10.7 - Prob. DQ Ch. 10.7 - Which step in the reaction would you expect to be...Ch. 10.7 - Prob. FQ Ch. 10.7 - Prob. GQ Ch. 10.8 - Prob. 10.11P Ch. 10.8 - Prob. AQ Ch. 10.8 - Prob. BQ Ch. 10.8 - Prob. CQ Ch. 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. 10.16P Ch. 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. 10.20P Ch. 10 - Prob. 10.21P Ch. 10 - Arrange the compounds in each set in order of...Ch. 10 - Prob. 10.23P Ch. 10 - The decalinols A and B can be equilibrated using...Ch. 10 - Prob. 10.25P Ch. 10 - Select the stronger acid from each pair and...Ch. 10 - Prob. 10.27P Ch. 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. 10.31P Ch. 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. 10.37P Ch. 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. 10.41P Ch. 10 - Prob. 10.42P Ch. 10 - The tosylate of a primary alcohol normally...Ch. 10 - Prob. 10.44P Ch. 10 - Show how to convert cyclohexene to each compound...Ch. 10 - Prob. 10.46P Ch. 10 - Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3)...Ch. 10 - Prob. 10.48P Ch. 10 - Prob. 10.49P Ch. 10 - Prob. 10.50P Ch. 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. 10.57P Ch. 10 - Prob. 10.58P Ch. 10 - Prob. 10.59P

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The tosylate of a primary alcohol normally undergoes an S N 2 reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula C 7 H 12 O. Propose a structural formula for this compound and a mechanism for its formation.

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Chapter 10 Solutions

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