Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 13, Problem 46P
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 solution
Students have asked these similar questions
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.
Compound 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.
Compound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD
I) Draw the structural formula of compounds AA, BB, CC and DD.
2)Name the type of chemical reaction for the formation of compound CC.
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 - Prob. 44PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 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. 2LGPCh. 13 - Prob. 1QCh. 13 - Prob. 2QCh. 13 - Prob. 3QCh. 13 - Prob. 4QCh. 13 - Prob. 5Q
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_forwardAromatic substitution can be done on naphthalene. Treatment of naphthalene with concentrated H2SO4 gives two (and only two) different sulfonic acids.arrow_forwardWhat is the structural requirement for a substance to react with ammoniacal AgNO3? Why would acetylene react with Tollen's reagent but not cyclohexane or cyclohexene?arrow_forward
- How to synthesize 1-phenyl-1-bromopropane from benzene?arrow_forwardA is a compound with molecular formula of C6H10, contains three methylene units. A react with one equivalent of H2 over Pd/C to yield B. A reacts with aqueous acid to form a single product, C. A also undergoes hydroboration/ oxidation to form product D. Ozonolysis of A followed by reaction of dimethylsulfide form E with molecular formula C6H10O2. A react with bromine in dichloromethane form F with molecular formula of C6H10Br2. Draw the reaction scheme for all the reaction mentioned above and suggest structure for A – F.arrow_forwardWhat reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forward
- Synthesize each compound from benzene and any other organic or inorganic reagents. NH2 NO2 Br. a. е. NH2 Br CH3 Br NH2 b. d. HOOC NO2 (РАВA) sunscreen componentarrow_forwardCan you please help with the attached question? Can you please add arrows, if possible, so that I will understand how you got the answer? Thank you for your help.arrow_forwardChlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?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