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 7.SE, Problem 29MP
When methyl vinyl ether reacts with a strong acid, the proton adds to C2 exclusively, instead of C1 or the oxygen atom. Draw the three protonated forms of methyl vinyl ether and explain this observation.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Pentalene, azulene, and heptalene are conjugated hydrocarbons that do not contain a benzene ring. Which hydrocarbons are especially stable or unstable based on the number of π electrons they contain? Explain your choices.
The major product of the following reaction exists as two stereoisomers. Draw both isomers: show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry (you don’t need to draw wedge and dash bonds for C-H bonds of CH3 and CH2 groups). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between two isomers.
Answer only f, g and h part .
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
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
- The bond dissociation energy of one of the C–H bonds is considerablyless than the bond dissociation energy of the other. Which C–H bondis weaker? Offer an explanation.arrow_forwardExplain why triphenylene resembles benzene in that it does not undergo addition reactions with Br2, but phenanthrene reacts with Br2 to yield the addition product drawn. (Hint: Draw resonance structures for both triphenylene and phenanthrene, and use them to determine how delocalized each π bond is.)arrow_forwardBelow is the structure for beta-carotene, a pigment found in plants and vegetables that give them their color. Determine how many alkenes are properly trans in the structure.arrow_forward
- When bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forwardN,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_forward1. Major product 2. Use arrowsarrow_forward
- 5. Isomeric compounds that rapidly interconvert by the movement of a proton like for example ketone formation from enol.arrow_forward10. Provide a structure of an isomer that has the molecular formula C5H8O2 and fits the criteria described below. Note that all of the structures must be neutral and not have any formal charges on any of the atoms. a) Contains an ester and an alkene b) A chiral compound that contains a ring, ether and ketone. c) Contains an alcohol and an alkyne. d) A meso compound that contains two alcohols.arrow_forwardGg.211.arrow_forward
- Write down the common (not IUPAC) names of the organic molecules that would be released if this molecule were hydrolyzed: CH2−O−C—(CH2);–CH=CH–CH2–CH=CH—(CH2)4—CH3 CH-O-C-(CH2)14-CH3 O 11 CH2−O−C— (CH2)14 — CH3 Separate each name with a comma. You will find useful information in the ALEKS Data resource. 1 010 Continue O a X 000 Y F8 F9 Submiarrow_forwardN,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. H3O+ 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. 90-87 0 + 11 ? n [arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Which of the alternative chair conformations of lindane is more stable? Explain.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
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License