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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Textbook Question
Chapter 10, Problem 10.53P
Using your reaction roadmap as a guide, show how to convert butane into 2-butanone. Show all reagents and all molecules synthesized along the way.
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Using your reaction roadmap as a guide, show how to convert butane into 2-butanone.
Show all reagents and all molecules synthesized along the way.
Butane
2-Butanone
Using your reaction roadmap as a guide, show how to convert ethylene into 1-butene.
All of the carbon atoms of the target molecule must be derived from ethylene. Show all
intermediate molecules synthesized along the way.
Ethylene
1-Butene
Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The
first step is the protonation of the alcohol oxygen to form an oxonium ion.
Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures,
including hydrogen atoms, of the three organic products of this reaction.
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CH3
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CH3
3-methyl-2-butanol
an oxonium ion
Major Product
Minor Product
Minor Product
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. 10.5PCh. 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. 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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- Using your reaction roadmaps as a guide, show how to convert ethylene into 2-methyl-1,3-dioxolane. You must use ethylene as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-bromopropane and carbon dioxide into 4-propyl-4-heptanol. You must use 1-bromopropane and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forwardUsing your reaction roadmap as a guide, show how to convert the starting trans-alkene to the cis-alkene in high yield. Show all intermediate molecules synthesized along the way.arrow_forward
- Using your reaction roadmaps as a guide, show how to convert 4-methyl-1-pentene and carbon dioxide into 5-methylhexanoic acid. You must use 4-methyl-1-pentene and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forwardStarting with acetylene (HCCH) or ethyne, show how you could synthesize benzylethylacetylene. Propose a mechanism for each step.arrow_forwardDiazomethane, CH2N2, is used in the organic chemistry laboratory despite its danger because it produces very high yields and is selective for reaction with carboxylic acids. Write the products of the following reactions.arrow_forward
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