Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) cyclooctanone

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) cyclooctanone

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.61P

See similar textbooks

Related questions

Q: Starting from bromobenzene and any other reagents and solvents you need, show how you would…

A: Using Grignard reagent and acyl chloride followed by wittig reaction - we finally get the desired…

Q: Show how you would convert 2-methylcyclopentanol to the following products. Any of these products…

A: The conversion of 2-methylcyclopenatnol to 1-methylcyclopentanol takes place in presence of acid.…

Q: From the table of available reagents select the one(s) you would use to accomplish the…

A: For the transformation of two reactions following reagents are required

Q: ! Which set of reagents (given below) would produce the products given in the following reaction?

A: We can see 2 double bonds in the reactant which got transformmed into epoxide

Q: Show how the following transformations may be accomplished in good yield. You mayuse any additional…

Q: Show how you would synthesize each compound from benzene, toluene, or phenol using the following…

A: Answer of the question given below,

Q: Show how you would accomplish the following syntheses.(a) benzene ¡ n@butylbenzene

A: Electrophilic aromatic substitution is shown by the aromatic compound, benzene. The reaction of an…

Q: Identify the product that can be obtained theoretically if the following reagents are mixed…

A: Toluene is a compound in which methyl group is present on the benzene ring. It does not reacts with…

Q: Show how you would synthesize octanal from each compound. You may use any necessary…

A: The given reagent is 1-bromohexane. The synthesis of octanal from the given compound with the use of…

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: Here, benzene will react with Butyl chloride in the presence of Lewis acid AlCl3, then obtained…

Q: Which reactions will produce the desired product in good yield? You may assume thataluminum chloride…

A: (a) Given: Benzenen+n-butyl bromide

Q: Predict the major products of the following reactions, and propose mechanisms tosupport your…

A: The given reaction is type of addition reaction and the addition reaction of alkene generally…

Q: Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides…

A: Given: (a) hex-1-yne

Q: Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides…

A: Given: (a) hex-1-yne (b) hex-2-yne

Q: Using bromocyclohexane as a starting material, how could you synthesize the following compound?

A: Given compound is shown below:

Q: Show how you would synthesize octan-2-one from each compound. You may use any necessary…

Q: Show how you might synthesize the following compound from a haloalkane and a nucleophile.

A: SN2 Reaction: It is a nucleophilic substitution reaction in which the rate determining step depends…

Q: Show how you would synthesize octan-2-one from each compound. You may use any necessary…

A: A strong acid catalyzed Markovnikov addition of water to an alkyne results the enol, this enol is…

Q: Using benzene and other reagents, synthesize the following molecule: Br NO2

A: We have to

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: The structure of 5-chloro-2-methylaniline is shown below.

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: Synthesis of 3-phenylpropan-1-ol:

Q: How might you synthesize the following substances from benzene? 4-chloro-1-nitro-2-propylbezene…

Q: Identify the product that can be obtained theoretically if the following reagents are mixed…

A: benzene involve in alkylation reaction with haloalkane in presence of Lewis acids like AlCl3,FeBr3…

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

Q: How would you synthesize 3-hexyne using ethane as your only carbon source? You may use any reagents.

A: The final product to be synthesized is 3-hexyne. The starting material should be a carbon source…

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: The formation of 1-bromo-4-methylbenzene from toluene is shown below.

Q: predict the products of the following substitution reactions, and specify whether each proceeds by…

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: Given starting material: Benzene (a) ethoxy benzene (b) 1,2-dichloro-4-nitrobenzene (c)…

Q: Show how to convert 1-phenylpropane into the following compound . In addition to this starting…

Q: Advanced Electron Pushing!! Provide a detailed, stepwise mechanism for the following…

A: NaOMe is very strong base so it take acidic hydrogen nearest to the carbonyl group.

Q: Show how would you synthesize the following compound, using the given starting material НО

Q: Starting from benzene, show how to prepare the following compound. Provide all necessary reagents…

Q: Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides…

A: The given compound to be synthesized is hex-3-yne. The starting reactant is acetylene and alkyl…

Q: Starting from bromobenzene and any other reagents and solvents you need, show how you would…

A: The given compound is 2-phenylbutan-2-ol. The starting material is bromobenzene.

Q: Show how you would synthesize the following compounds, starting with acetylene and any compounds…

A: First Acetylene reacts with sodium amide in presence of 1-bromopropane to form pent-1-yne.

Q: Propose a synthesis of the molecule below starting with hept-6-en-2-one be sure to include all…

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: The answer for part (a) is given below. Kindly repost the other parts as separate one.

Q: Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides…

Q: Using hex-1-ene as your starting material, show how you would synthesize the following compounds.…

A: Structure of hex-1-ene and hexan-2-one is as follows.

Q: Show how you might synthesize the following compounds, using acetylene and anysuitable alkyl halides…

A: The organic reactions are carried out in many steps with the help of various reagents.

Q: Show how you would synthesize the following compounds, starting with benzene or toluene and any…

A: The synthesis of 4-butylphenol from benzene has to be shown.

Q: Show how you would convert 2-methylcyclopentanol to the following products. Any of these products…

Q: Write out the complete forward synthesis of the target molecule below beginning with the precursor…

A: Alkyl bromide converted into alkylmagnesiumbromide Grignard reagent reacts with CO2 to give…

Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have
shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)
cyclooctanone

Expert Solution

Step 1

Given compound is:

Cyclooctyne.

Required product from cyclooctyne is:

Cyclooctanone.

Step 2

The structure of cyclooctyne is shown below:

which is an alkyne.

The structure of cyclooctanone is:

which is an example of ketone.

Alkynes can be converted into ketones by the reaction with dilute sulphuric acid in presence of mercuric sulphate.

Step by step

Solved in 3 steps with 3 images

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

Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) ) cyclooctane
Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) ) trans-1,2-dibromocyclooctane
Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) hex-1-yne
Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as thereactant in any subsequent part of this problem.(a) 1-methylcyclopentene
Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) e) 1,1-dibromocyclooctane
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
All rearrangements we have discussed so far have involved generation of an electron-deficient carbon followed by a 1,2-shift of an atom or a group of atoms from an adjacent atom to the electron-deficient carbon. Rearrangements by a 1,2-shift can also occur following the generation of an electron-deficient oxygen. Propose a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide to phenol and acetone.
A newer generation of antipsychotics, among them clozapine, are now used to treat the symptoms of schizophrenia. These drugs are more effective than earlier drugs in improving patient response in the areas of social withdrawal, apathy, memory, comprehension, and judgment. They also produce fewer side effects such as seizures and tardive dyskinesia (involuntary body movements). In the following synthesis of clozapine, Step 1 is an Ullmann coupling, a type of nucleophilic aromatic substitution that uses a copper catalyst. (a) Show how you might bring about formation of the amide in Step 2. (b) Propose a reagent for Step 3. (c) Propose a mechanism for Step 4. (d) Is clozapine chiral? If so, how many of the possible stereoisomers are formed in this synthesis?
Show how to synthesize the following product as the major product starting with 2,2-dimethylpropane as the starting material. You may use additional reagents and any number of steps. Be sure to list each step with all reactants/reagents/conditions required. (Do not use hydrogenation reactions). Write the process.
When ethoxybenzene is treated with a mixture of nitric acid and sulfuric acid, two products are obtained, each of which has the molecular formula C8H9NO3.For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.
Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the followingcompounds. Any of these products may be used as starting materials in subsequent parts of this problem. 2-phenylbut-2-ene
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.