ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 7, Problem 65DSP
Interpretation Introduction
Interpretation:
The arrow to whichZaitsev's rule most closely relates from a mechanistic perspective is to be identified.
Concept Introduction:
>During elimination reaction, the hydrogen atom is removed from a beta carbon atom.
>According to Zaitsev's rule, if there are more than one type of beta carbon atoms, then the major product is the one having the proton removed from the beta carbon having the fewest number of hydrogens.
>The more substituted
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C— OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown in Equation [1]. Using this information, draw a stepwise mechanism for the reaction shown in Equation [2]. We will see another example of this type of rearrangement in Section 16.5C.
Several reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product 3-bromo-2-methyl-2-butanol by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used.
Organic chemistry student Everett has set up two separate electrophilic addition reactions with 2-butyne (shown below). In reaction (i) the alkyne is treated with 1 equivalent of HBr, which successful provides (Z)-2-bromo-2-butene. In reaction (ii) the alkyne is subjected to a two-step hydroboroation/oxidation sequence. Interestingly, Everett’s second reaction fails to provide the desired methyl ketone and instead has provided butan-2,3-diol. (a) Provide the structure of intermediate X form the first step of reaction (ii). (b) Briefly explain (use structures if necessary) why reaction (i) provided an alkene where as reaction (ii) provided an alkane when only 1 equivalent of the electrophile was used in each reaction.
Chapter 7 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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
- Which of the following statements is TRUE regarding the reaction below? Options: The IR spectrum of the major organic product will show a broad absorption between 3000-3500 cm-1. The mass spectrum of the major organic product will show an M+2 peak in the molecular ion region. The reaction should proceed without carbocation rearrangement. The alkene is the electrophile and water is the nucleophile in the first step. HSO4- is the dominant nucleophile in the second step.arrow_forwardShow stereo chemistry and possible outcomes and the steps for the reaction.arrow_forwardPlease give major organic products along with mechanism. Please also identify what type of reaction it is (SN1, SN2, E1, E2)arrow_forward
- Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with sodium methoxide. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Also indicate which step is likely to be rate-determining. The answer you sent before will be used for this question.arrow_forward1. i.What are the various ways by which alkenes may be synthesized? ii. Give two examples each of Unsymmetrical alkenes and reagents. iii. Give two examples of reactions of alkenes that result in Anti-Markonikov’s addition productsarrow_forwardConsider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply? Involves a carbocation intermediatearrow_forward
- iii) 2-Bromo-2-cyclopropylpropane will undergo an SN1 reaction called solvolysis in methanol to give several products, two of which are shown below. Use curly arrows to show how the formation of these two products occurs mechanistically.arrow_forwardPlease answer this NEATLY, COMPLETELY, and CORRECTLY for an UPVOTE. Which of the following reactions will involve rearrangement? A) Acid-catalyzed addition of H2O to an alkene. B) E2 elimination. C) Free radical halogenation of alkanes. D) Addition of Cl2 to an alkene. E) None of the choices is correct.arrow_forwardSecondary alcohols are often dehydrated in an E2 reaction to give an alkene. Elimination follows Zaitsev's rule to give the more substituted alkene as the major product. Since the reaction occurs via an E2 mechanism, there is no risk of rearrangement of the carbon skeleton as could possibly occur if the elimination occurred via an E1 mechanism with a carbocation intermediate.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forward
- please answer part two (Please answer "What is BP of the solvent, and the authors state... why is that important"). thank you "The 3-Sulfolene is the prime molecule used for synthesis for the 1,3-butadiene molecule. The mechanism involves breaking of two C-S bonds in 3-sulfolene to generate 1,3-butadiene in the presence of heat. The reaction can be shown as below: This reaction is a type of pericyclic reaction that involves breaking and making of bonds in a single step and hence there will be no intermediate formed. The solvent used here is water." https://www.bartleby.com/questions-and-answers/3-sulfolene-a-butadiene-source-for-a-diels-alde-synthesis.-please-be-prepared-to-take-a-quiz-on-this/8bf8358d-dbdf-46f9-97db-6f744d66c0cdarrow_forwardConsider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply? Order of reactivity of haloalkanes is methyl . 1° > 2° > 3°.arrow_forwardPart 1 regards the images.Part 2: Identify the 4 unique common elementary steps in the above mechanism. (Electrophilic addition, Carbocation rearrangement, Bimolecular nucleophilic substitution (SN2), Nucleophilic addition, Nucleophile elimination, Bimolecular elimination (E2), Coordination, Proton transfer, Electrophile elimination, Heterolysis).Part 3: Fill in the blank: Both E1 and E2 produce the ___ alkene.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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY