Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7, Problem 58DSP
Interpretation Introduction
Interpretation:
Out of the arrows
Concept Introduction:
>Alcohols, upon reaction with an acid, are first protonated to form a good leaving group. Then the formation of carbocation takes place.
>Reaction of the carbocation with a nucleophile forms the required product of substitution.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents 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.
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.
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.
Chapter 7 Solutions
Organic Chemistry - Standalone book
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
- Consider 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_forwardplease 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_forwardWhich 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_forward
- Show stereo chemistry and possible outcomes and the steps for the reaction.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_forwardGive 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_forward
- The Wolff–Kishner reaction uses hydrazine (H2NNH2) and hydroxide (–OH) to reduce a carbonyl to the alkane. The first steps of the mechanism convert a carbonyl to a hydrazone in a manner similar to imine formation. Draw the mechanism arrows for the reaction from the hydrazone to the alkane. Be sure to add lone pairs of electrons and nonzero formal charges to all species.arrow_forwardiii) 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_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 give major organic products along with mechanism. Please also identify what type of reaction it is (SN1, SN2, E1, E2)arrow_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_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_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
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