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
Concept explainers
Question
Chapter 13, Problem 46P
Interpretation Introduction
Interpretation:
The synthesis of norbornadiene by using cyclopentadiene and acetylene, and cyclopentadiene and vinyl chloride is to be described.
Concept introduction:
Diels-alder is a type of organic reaction in which a substituted
The general reaction of Diels-alder is as follows:
Aldrin is an organic compound that contains chloride groups. It is also known as an organochlorine compound. Aldrin is toxic in nature and is used as insecticides.
Norbornadiene is an organic compound used as dienophile in Diels-alder reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.
(b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.
(i) Draw TWO (2) possible structures for compound B.
(ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.
(iii) Name the product formed when compound A undergoes bromination reaction.
The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rainforests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.
Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2S
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGP
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 endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resultingconjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.arrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forwardFirst calculate the number if moles of the given compounds.arrow_forward
- Which 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(a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the product formed. (b) Predict the product(s) will be formed from the following reactions: (i) Bromination of p-methylbenzoic acid (ii) Sulphonation of m-bromoanisole (iii) Friedel-craft acylation of o-bromonitrobenzenearrow_forwardDevelop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forward
- 11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…arrow_forwardWrite the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexenearrow_forwardGive the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2arrow_forward
- (a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentanearrow_forwardCyclopentene reacts with reacts with ozone in dichloromethane at -78° C. Treatment of the resulting ozonide with zinc in acetic acid or with dimethylsulfide gives A(C3H3O2). Treatment of A with sodium borohydride in ethanol gives B(C3H12O2). Draw the structure of B.arrow_forwardCompound A of molecular formula C8H₁4 is reduced by sodium in liquid ammonia to give compound of molecular formula C8H16. product (Y). Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5- dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H₁40 product, but reaction with bromine gives an achiral C8H₁4Br2 product. What are the identities of A and B? 14 A is 2,5-dimethyl-3-hexyne; B is cis-2,5-dimethyl-3-hexene A is 2,5-dimethyl-3-hexyne; B is trans-2,5-dimethyl-3-hexene A is 2,5-dimethyl-1,5-hexadiene; B is 2,5-dimethyl-3-hexyne A is 2,5-dimethyl-2,4-hexadiene; B is cis-2,5-dimethyl-3-hexenearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
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