Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 7, Problem 42PP
Interpretation Introduction
Interpretation:
The conditions that ensure elimination over substitution and the conditions that ensure the highest yield of ether are to be determined.
Concept introduction:
The order of stability of carbocation is such that the tertiary carbocation is most stable whereas the primary carbocation is least stable, and the secondary carbocation lies between the primary and secondary carbocations.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise?
2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia.
(i) What do you understand by the term nucleophile?
(ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles?
3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?
Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-methyl-2-heptene as shown in the following equation.(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?
Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 1PPCh. 7 - Prob. 2PPCh. 7 - Prob. 3PPCh. 7 - Prob. 4PPCh. 7 - Practice Problem 7.5
How many stereoisomers are...Ch. 7 - Prob. 6PPCh. 7 - Prob. 7PPCh. 7 - PRACTICE PROBLEM 7.8
Examine Solved Problem 7.3....Ch. 7 - Prob. 9PPCh. 7 - Practice Problem 7.10 When...
Ch. 7 - Practice Problem 7.11
(a) When...Ch. 7 - Prob. 12PPCh. 7 - Prob. 13PPCh. 7 - Practice Problem 7.14
Dehydration of 2-propanol...Ch. 7 - Practice Problem 7.15
Rank the following alcohols...Ch. 7 - Practice Problem 7.16
Acid-catalyzed dehydration...Ch. 7 - Practice Problem 7.17 Acid-catalyzed dehydration...Ch. 7 - Prob. 18PPCh. 7 - Prob. 19PPCh. 7 - Practice Problem 7.20
Show how you might...Ch. 7 - Prob. 21PPCh. 7 - Prob. 22PPCh. 7 - Practice Problem 7.23
Write the structure of...Ch. 7 - Prob. 24PPCh. 7 - Prob. 25PPCh. 7 - Practice Problem 7.26 (a) Devise retrosynthetic...Ch. 7 - Each of the following names is incorrect, Give the...Ch. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Give the IUPAC names for each of the following:...Ch. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - 7.35. Write structural formulas for all the...Ch. 7 - 7.36. Explain the following observations: When...Ch. 7 - Prob. 37PCh. 7 - Arrange the following alcohols in order of their...Ch. 7 - Prob. 39PPCh. 7 - Prob. 40PPCh. 7 - Prob. 41PPCh. 7 - Prob. 42PPCh. 7 - Your task is to prepare isopropyl methyl ether by...Ch. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - 7.47. Starting with an appropriate alkyl halide...Ch. 7 - Prob. 48PCh. 7 - 7.49. What is the index of hydrogen deficiency...Ch. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Compounds I and J both have the molecular formula...Ch. 7 - Prob. 53PCh. 7 - 7.54. Outline a synthesis of phenylethyne from...Ch. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - cis-4-Bromocyclohexanol tBuOHtBuO racemic C6H10O...Ch. 7 - Prob. 59PPCh. 7 - Consider the interconversion of cis-2-butene and...Ch. 7 - Prob. 61PCh. 7 - (a) Using reactions studied in this chapter, show...Ch. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - 1. Write the structure(s) of the major product(s)...Ch. 7 - Prob. 2LGPCh. 7 - (a) Write the structure of the product(s) formed...Ch. 7 - Prob. 4LGP
Knowledge Booster
Similar questions
- 3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxidearrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexenearrow_forward
- Write IUPAC name of the products obtained by addition reactions of HBr to hex – 1 –ene.(i) in the absence of peroxide, and(ii) in the presence of peroxide.arrow_forward(a) rate at which the following alcohols undergo dehydration to form alkenes in sulfuric acid OH OH OH (b) rate at which the following alkenes undergo addition with HBr to form an alkyl halidearrow_forwardWhich of the following is true for the reactions of alkyl halides? (a) The characteristic reactions of alkyl halides are oxidation and reduction.(b) The characteristic reactions of alkyl halides are elimination and substitutionc. The characteristic reactions of alkyl halides are addition and substitutiond. Characteristic reactions of alkyl halides are addition and elimination.arrow_forward
- The rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forwardWhich of the following statements is/are true regarding Alkene A and the products of an ozonolysis (O_(3)) reaction? (i) One of the alkene carbon atoms of alkene A is disubstituted and the other is monosubstituted (ii) One of the alkene carbon atoms of alkene A is monosubstituted and the other is unsubstituted (iii) Ozonolysis of alkene A followed by work up under reductive conditions gives products 1 and 2, but if work up is under oxidative conditions products 1 and 3 form (iv) Ozonolysis of alkene A followed by work up under reductive conditions gives products 1 and 3 but if work up is under oxidative conditions products 1 and 2 form.. a. (i) and (iii) are truearrow_forward(a) One test for the presence of an alkene is to add a smallamount of bromine, which is a red-brown liquid, and lookfor the disappearance of the red-brown color. This test doesnot work for detecting the presence of an aromatic hydrocarbon.Explain. (b) Write a series of reactions leading topara-bromoethylbenzene, beginning with benzene andusing other reagents as needed. What isomeric side productsmight also be formed?arrow_forward
- The rate law for addition of Br2Br2 to an alkene is first order in Br2Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2Br2 to an alkene proceeds in the same manner as for addition of HBr? Explain.arrow_forwardPhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY