Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 6.SE, Problem 25EDRM
When isopropylidenecyclohexane is treated with strong acid at room temperature, isomerization occurs by the mechanism shown below to yield 1-isopropylcyclohexene:
At equilibrium, the product mixture contains about 30% isopropyl-idenecyclohexane and about 70% 1-isopropylcyclohexene.
(a) What is an approximate value of Keq for the reaction?
(b) Since the reaction occurs slowly at room temperature, what is its approximate ∆G‡?
(c) Draw an energy diagram for the reaction.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
When A is reacted with hot aqueous NaOH, a compound B of molecular formula C8H11NO is produced. With this information, write the correct structure of B and propose the reaction mechanism (step by step, with the correct use of arrows) to obtain B.
The sex attractant by which the female housefly attracts the male has the molecular formula C23H46. Catalytic hydrogenation yields an alkane of molecular formula C23H48. Ozonolysis yieldsWhat is the structure of the housefly sex attractant?
An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.
Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Prob. 1PCh. 6.3 - Prob. 2PCh. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4PCh. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8PCh. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...
Ch. 6.7 - Prob. 11PCh. 6.9 - Which reaction is faster, one with ∆G‡ = +45...Ch. 6.10 - Prob. 13PCh. 6.SE - Prob. 14VCCh. 6.SE - Prob. 15VCCh. 6.SE - Prob. 16VCCh. 6.SE - Look at the following energy diagram: (a) Is...Ch. 6.SE - Look at the following energy diagram for an...Ch. 6.SE - What is the difference between a transition state...Ch. 6.SE - Prob. 20EDRMCh. 6.SE - Prob. 21EDRMCh. 6.SE - Draw an energy diagram for a two-step exergonic...Ch. 6.SE - Draw an energy diagram for a reaction with keq =...Ch. 6.SE - The addition of water to ethylene to yield ethanol...Ch. 6.SE - When isopropylidenecyclohexane is treated with...Ch. 6.SE - Prob. 26EDRMCh. 6.SE - Draw the electron-pushing mechanism for each...Ch. 6.SE - Draw the complete mechanism for each polar...Ch. 6.SE - Prob. 29EDRMCh. 6.SE - Identify the functional groups in the following...Ch. 6.SE - Identify the following reactions as additions,...Ch. 6.SE - Identify the likely electrophilic and nucleophilic...Ch. 6.SE - For each reaction below identify the electrophile...Ch. 6.SE - Prob. 34APCh. 6.SE - Follow the flow of electrons indicated by the...Ch. 6.SE - Prob. 36APCh. 6.SE - Prob. 37APCh. 6.SE - Despite the limitations of radical chlorination of...Ch. 6.SE - Prob. 39APCh. 6.SE - Answer question 6-39 taking all stereoisomers into...Ch. 6.SE - Prob. 41APCh. 6.SE - Prob. 42APCh. 6.SE - Prob. 43APCh. 6.SE - The reaction of hydroxide ion with chloromethane...Ch. 6.SE - Prob. 45APCh. 6.SE - Ammonia reacts with acetyl chloride (CH3COCl) to...Ch. 6.SE - The naturally occurring molecule α-terpineol is...Ch. 6.SE - Prob. 48APCh. 6.SE - Prob. 49APCh. 6.SE - Draw the structures of the two carbocation...
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
- 3b）Give the mechanisms for the following transformations:arrow_forwardWhen cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardCyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.arrow_forwardReaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.arrow_forward
- Alcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with potassium hydrogen sulfate (KHSO4). Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol A proceeds without rearrangement, deduce the structures of alcohol A and alkene C.arrow_forwardCompound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and Carrow_forward2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (i) Draw the structural formula of compounds W, X and Yarrow_forward
- Hydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forwardIsoprene has sometimes been used as a starting material in the laboratory synthesis of terpenes. In one such synthesis, the first step is the electrophilic addition of 2 mol of hydrogen bromide to isoprene to give 1,3-dibromo-3-methylbutane.Write a series of equations describing the mechanism of this reaction.arrow_forwardHydroboration of 2-methyl-2-pentene at 25°C, followed by oxidation with alkaline H2o2, yields 2-methyl-3-pentanol, but hydroboration at 160°C followed by oxidation yields 4-methyl-1-pentanol. Suggest a mechanism.arrow_forward
arrow_back_ios
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
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY