EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 13, Problem 45P
Two controversial “hard” insecticides are aldrin and dieldrin. [The Environmental Protection Agency (EPA) halted the use of these insecticides because of possible harmful side effects and because they are not biodegradable.] The commercial synthesis of aldrin began with hexachlorocyclopentadiene and norbornadiene. Dieldrin was synthesized from aldrin. Show how these syntheses might have been carried out.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Enanthotoxin is an extremely poisonous organic compound found in hemlock water drop-
wart, which is reputed to be the most poisonous plant in England. It is believed that no
British plant has been responsible for more fatal accidents. The most poisonous part of
the plant is the roots, which resemble small white carrots, giving the plant the name"five
finger death."Also poisonous are its leaves, which look like parsley. Enanthotoxin is thought
to interfere with the Nat current in nerve cells, which leads to convulsions and death.
он
How many stereoisomers are possible for enanthotoxin?
Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized.
Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.
Kepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.
Chapter 13 Solutions
EBK 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
Additional Science Textbook Solutions
Find more solutions based on key concepts
Classify each process as exothermic or endothermic. a. dry ice subliming (changing from a solid directly to a g...
Introductory Chemistry (6th Edition)
If isomer A is heated to about 100 C, a mixture of isomers A and B is formed. Explain why there is no trace of ...
Organic Chemistry
The Lyman series of the hydrogen spectrum can be represented by the equation v=3.22811015s1(1121n2)(wheren=2,3,...
General Chemistry: Principles and Modern Applications (11th Edition)
The density of the gas is to be calculated when pressure, temperature and volume of the gas are given. Concept ...
Chemistry: Matter and Change
For each of the following, (i) give the systematic name of the compound and specify the oxidation state of the ...
General Chemistry: Atoms First
2. A schedule of experiments for a laboratory indicates that the 1-bromobutane preparation is paired with the p...
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
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
- Show how to bring about each step in this synthesis of the herbicide propranil.arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardSeveral diamines are building blocks for the synthesis of pharmaceuticals and agro-chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be prepared from acrylonitrile.arrow_forward
- The compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardCompound F may be synthesised by the method attached: When 2-chloropropane treated with NaOH and 1-chloropropane treated with NaOH separately produce two different functional groups. Provide both reactions and explain the two different functional groups produced.arrow_forwardAromatic substitution can be done on naphthalene. Treatment of naphthalene with concentrated H2SO4 gives two (and only two) different sulfonic acids.arrow_forward
- Which of the following compounds produces an aldehyde when treated with catalytic sulfuric acid in aqueous solution? A) Compound I B) Compound II C) Compound III D) Compound IVarrow_forwardEast Indian sandalwood oil contains a hydrocarbon given the name santene (C9H14). Ozonolysis of santene gives the compound shown. What is the structure of santene?arrow_forwardShow how you would synthesize each compound from benzene, toluene, or phenol using the following reactions: Reactions 1. Halogenation 2. Nitration 3. Sulfonation 4. Friedel-Crafts acylation 5. Friedel-Crafts alkylation 6. Oxidation of methyl group 7. Reduction of nitro group • Choose the starting material from the drop-down list • Enter the number(s) of the desired reactions in the order that you wish to use them without commas between • If a reaction is used more than once, enter its number each time you wish to use it Compound 1: 5-chloro-2-methylbenzenesulfonic acid Starting material: toluene Reaction(s): 31 Compound 2: m-bromobenzoic acid Starting material: [benzene Reaction(s): Submit Answer Try Another Version 1 item attempt remainingarrow_forward
- Jj.128.arrow_forwardStarting material options: benzene, toluene, phenolarrow_forwardIn an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol. Ethanol is often present in the technical grade of diethyl ether. If this grade rather than anhydrous were used, what effect, if any, would the ethanol have on the formation of the Grignard reagent? 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
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