Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 7.SE, Problem 69AP
Interpretation Introduction
Interpretation:
An energy diagram for the addition of HBr to 1-pentene is to be drawn. Both the curves, one for the formation of 1-bromopentane and another for the formation of 2-bromopentane, are to be shown in the same diagram indicating the positions of all the reactants, intermediates and products.The curve which has the higher-energy carbocation intermediate and that which has the higher-energy first transition state are to be identified.
Concept introduction:
The carbocation II is more stable than I. Hence it is easily formed, has less energy and its formation will be more exergonic.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
What about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?
What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-
butanol?
Loss of a b-hydrogen from the carbocation to form an alkene.
Protonation of the alcohol to form an oxonium ion.
Loss of water from the oxonium ion to form a carbocation.
The simultaneous loss of a B-hydrogen and water from the oxonium ion.
For each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction. Don't worry about the absolute energy of starting materials and products but you can assume that the product is more stable than the starting materials.
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2PCh. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5PCh. 7.3 - Prob. 6PCh. 7.3 - Prob. 7PCh. 7.4 - Prob. 8PCh. 7.4 - Prob. 9PCh. 7.4 - Prob. 10P
Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Prob. 12PCh. 7.5 - Prob. 13PCh. 7.5 - Prob. 14PCh. 7.6 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.10 - Prob. 20PCh. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Prob. 22VCCh. 7.SE - Prob. 23VCCh. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - Prob. 25VCCh. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Prob. 27MPCh. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - Prob. 33MPCh. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - Prob. 35APCh. 7.SE - Prob. 36APCh. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Prob. 39APCh. 7.SE - Prob. 40APCh. 7.SE - Prob. 41APCh. 7.SE - Prob. 42APCh. 7.SE - Prob. 43APCh. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Prob. 45APCh. 7.SE - Prob. 46APCh. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Prob. 48APCh. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Prob. 50APCh. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Prob. 53APCh. 7.SE - Prob. 54APCh. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Prob. 56APCh. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Prob. 58APCh. 7.SE - Prob. 59APCh. 7.SE - Prob. 60APCh. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Prob. 64APCh. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Prob. 67APCh. 7.SE - Prob. 68APCh. 7.SE - Prob. 69APCh. 7.SE - Prob. 70APCh. 7.SE - Prob. 71APCh. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...
Knowledge Booster
Similar questions
- HBr addition to ethylene is exothermic. What does this mean? Options: The rate determining step is the first step. The newly formed bonds are more stable (higher dissociation energy) than those broken in the reactants. The carbocation intermediate is higher energy than the alkene. The reaction is very fast.arrow_forwardDraw structural formulas for organic products A and B in the window below. Mg H20 A H3CC=CH2 ether Br • Draw only products having the organic portion of the original alkyl halide. • Draw carbon-lithium bonds using the single bond tool. If a structure has a copper-lithium bond, do not draw the lithium. • Separate products from different steps using the → sign from the drop-down menu.arrow_forwardBased on the characteristics of the carbonyl group (C = O), what reactions or transformations take place with aldehydes and ketones? a. nucleophilic additions by oxygenb. electrophilic additions by carbon attackc. nucleophilic additions by carbon attackd. electrophilic substitutions through a carbocationand. acid-base because carbonyl can act as both an electrophile and a nucleophilearrow_forward
- Ff.269. Draw the energy diagram beginning with 2-butanol that displays the conversion of 2-butanol into the three products produced in the dehydration of 2-butanol.arrow_forwardComplete the following oxidation reaction by drawing a structural formula for the product. CH3CH2CHÖ-H CH2CH3 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forwardCarvone is the major constituent of spearmint oil. Draw the major organic product of the reaction of carvone with HOCH2CH2OH, HCI. Carvone • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material. + Sn 1arrow_forward
- Draw a structural formula for the substitution product of the reaction shown below. Br H NH3 CH₂OH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If more than one stereoisomer of product is formed, draw both. • Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms.arrow_forward2arrow_forwardFree radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?arrow_forward
- N,N-diethyl-m-toluamide (DEET) is the active ingredient in many insect repellent preparations. Following is one of the steps in its synthesis. In the box below draw the structure of the product of this reaction. H3C MgBr 1. CO₂ 2. H₂O* product • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw the Grignard reagent as a covalent magnesium bromide.arrow_forwardOH 1. NaOH, EtOH 2. n-BuBr A nucleophilic substitution reaction is a frequently used method to convert one functional group into another. A nucleophile is mixed with an electrophile and the nucleophile replaces the leaving group to produce a new compound. In this experiment, a weak nucleophile (2-naphthol) is converted into a strong nucleophile by deprotonation with sodium hydroxide. Then this strong nucleophile, now with a negative charge, reacts with alkyl halide to yield an ether, 2-butoxynaphthalene. 2-butoxynaphthalene is a flavoring agent that has strong fruit smell like raspberry and strawberry.arrow_forward3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry: An Atoms First Approach
Chemistry
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning