We said that organometallic compounds are often used to make carbon-carbon bonds.Specifically, with Grignard reagents and organolithium reagents making this new bondleads to alcohols.Identify a compound with molecular formula C5H1002 that would react withEthylmagnesium bromide to generate the corresponding product in the table below andthen give the structure of the product. There are multiple correct answers.CompoundASecondary alcoholBсDEFProductSecondary alcoholTertiary alcohol where only one of the three groups in the alcoholcomes from the GrignardTertiary alcohol where two of the three groups in the alcoholcome from the GrignardReacts with Grignard to make Ethane (rather than an alcohol)No Reaction with the GrignardExampleStructure of starting compound:AHProduct structure:HH

Step 1:Determine the possible functional groups present in the compound. The compound has the…

Answered: We said that organometallic compounds…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)
Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.
The structure below is the cyclic ether (epoxide), butene oxide: (1) CH3CH₂ -CH₂ butene oxide How could this compound be prepared from but-1-ene? Explain why butene oxide is much more reactive than its isomer, tetrahydrofuran, which is also a cyclic ether: H₂C-CH₂ H₂C CH₂ tetrahydrofuran Illustrate how butene oxide reacts with ammonia, showing details of the mechanism leading to the final product, C4H11 NO.
The proton NMR spectrum of a compound with formula C8H14O2 is shown. TheDEPT experimental results are tabulated. The infrared spectrum showsmedium-sized bands at 3055, 2960, 2875, and 1660 cm-1and strong bands at1725 and 1185 cm-1. Draw the structure of this compound and assign thecarbon peaks.
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Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.
10. M and N are amines with the molecular formula C3H»N. Reaction of M with sodium nitrite and HCI releases nitrogen gas and produces a mixture of X and Y and Propanol while N produces a yellowish oily compound, S when reacted with the same reagents. Give the structures of M, N, X, Y, and S. Outline the synthesis of M from a suitable alkene.
The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
An unknown hydrocarbon Q has a formula C6H12. Q reacts with osmium tetroxide to give a diol R when oxidized with KMnQ4 in an acidic medium Q gives two products. One product is propanoic acid and the other is ketone S. Provide reaction equations to identify the possible structures of Q, R and S.

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