Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 6, Problem 6.51P
In this chapter, we studied the mechanism of the acid-catalyzed hydration of an
Propene
2-Propanol
(Isopropyl alcohol)
Propose a mechanism for the acid-catalyzed dehydration of 2-propanol to propene.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. Propose a mechanism for this reaction.
Acid-catalyzed dehydration of 3-methyl-2-butanol gives three alkenes: 2-methyl-2- butene, 3-methyl-1-butene, and 2-methyl-1-butene. Propose a mechanism to account for the formation of each product
Draw structural formulas for the alkenes formed by acid-catalyzed dehydration of each alcohol. Where isomeric alkenes are possible, predict which is the major product.
Q.) 2-Methyl-2-butanol
Chapter 6 Solutions
Organic Chemistry
Ch. 6.2 - Using the BDE values from Appendix 3, calculate...Ch. 6.3 - Name and draw a structural formula for the product...Ch. 6.3 - Prob. 6.3PCh. 6.3 - Propose a mechanism for the addition of HI to...Ch. 6.3 - Prob. 6.5PCh. 6.3 - Propose a mechanism for the acid-catalyzed...Ch. 6.3 - The acid-catalyzed hydration of...Ch. 6.3 - Complete these reactions. (a) (b)Ch. 6.3 - Draw the structure of the chlorohydrin formed by...Ch. 6.4 - Draw structural formulas for the alkene that gives...
Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing functional group.arrow_forwardWhen 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forward
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardCHEMICAL REACTIONS: Illustrate and predict the products of the given chemical reactions below including the correct catalyst for each given reactions Reduction or Hydrogenation of 2-butanone by a metal catalyst.arrow_forwardThe acid-catalyzed hydration of 3,3-dimethyl-1-butene gives 2,3-dimethyl- 2- butanol as the major product. Propose a mechanism for the formation of this alcoholarrow_forward
- The alkene mixture obtained on the dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene Draw the structures of 1,2-dimethylcyclohexene Show the mechanism for the formation of this alkene product Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reactionarrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardDissolving formaldehyde in water causes the solution to contain gem-diol CH2 (OH)2. Write down the steps for the formation of formaldehyde.arrow_forward
- Need help with this Propose a preparation reaction for the formation of CH3NHCH2CH3 from organic compounds with only 1 or 2 carbonsarrow_forwardGive the products, if any, of the benzene + 2 CH3Cl + AlCl3 reaction:arrow_forwardWhen (CH3CH2)3CBr is added to CH3OH at room temperature, the major product is (CH3O)C(CH2CH3)3 and a minor product is CH3CH=C(CH2CH3)2. Propose a mechanism for the product that is formed by the substitution reaction. Use curved arrows to show the movement of electrons.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY