|| H₂C=CHCCH3 8 11.8 then H₂O* The Michael reaction is a conjugate addition process wherein a nucleophilic enolate anion (the donor) reacts with an as-unsaturated carbonyl compound (the acceptor). The best Michael reactions are those that take place when a particularly stable enolate anion is formed via treatment of the donor with a strong base. Alternatively, milder conditions can be used if an enamine is chosen as the donor, this variant is termed the Stork reaction. In the second step, the donor adds to the ẞ-carbon of the acceptor in a conjugate addition, generating a new enolate. The enolate abstracts a proton from solvent or from a new donor molecule to give the conjugate addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions да

|| H₂C=CHCCH3 8 11.8 then H₂O* The Michael reaction is a conjugate addition process wherein a nucleophilic enolate anion (the donor) reacts with an as-unsaturated carbonyl compound (the acceptor). The best Michael reactions are those that take place when a particularly stable enolate anion is formed via treatment of the donor with a strong base. Alternatively, milder conditions can be used if an enamine is chosen as the donor, this variant is termed the Stork reaction. In the second step, the donor adds to the ẞ-carbon of the acceptor in a conjugate addition, generating a new enolate. The enolate abstracts a proton from solvent or from a new donor molecule to give the conjugate addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions да

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 62GP: The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a...

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2 Moin H3C H H₂C C⇒x= base :0: OH Hori H3C H. The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a B-hydroxy carbonyl compound. Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H₂C Ἡ :0: heat H Home H3C + H₂O
2) When conjugated aldehydes or ketones are attacked by a nucleophile, often more than one product forms. Please show resonance structures to explain which positions in the following conjugated ketone can react with NaBH4. Which product(s) can form? + H н-вн Na H CH3OH
H Br Br2 CH2Cl2 H, Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH2Clɔ. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H Br H- Br H. :Br: Proviouc Noxt
H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3
Identify the best reagents to complete the following reaction. HO, CI
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3A Complete the reactions below. H₂SO4/H₂O HgSO4 A NaBH4 EtOH B лH₂SO4 C
The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and the iodomethane product is distilled off and passed into an alcohol solution of AgNO3, where it reacts to form a precipitate of silver iodide. The Agl is then collected and weighed, and the percentage of methoxyl groups in the sample is thereby determined. For example, 1.06 g of vanillin, the material responsible for the characteristic odor of vanilla, yields 1.60 g of Agl. If vanillin has a molecular weight of 152, how many methoxyl groups does it contain?
base 2 H3C H H3C OH heat H H3C + H₂O H The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ẞ-hydroxy carbonyl compound. Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ẞ-hydroxyl group is eliminated in an E1CB dehydration to give an a,ẞ-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions X :OH H₂O: а کی H₂C H H₂C H H
Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? но OH но он || II IV
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In nucleophilic acyl substitution what is true? V addition to the carbonyl by a nucleophile is followed by loss of the leaving group. O Tetrahedral intermediate is formed. O loss of the leaving group is followed by rearrangement of the carbocation. O an SN2 reaction occurs. O protonation of the carbonyl is followed immediately by loss of the leaving group. 4>A 144 & 7 8 R T Y