HOAldol reactions (condensation of two aldehydes or ketones to yield a ẞ-hydroxy carbonyl) can go inreverse (ẞ-hydroxy carbonyl to two aldehyde/ketones, a retro-aldol). Propose mechanisms for thefollowing two transformations, using both intra-molecular aldol and a retro-aldol reactions. Be sureto follow the rules we have discussed for writing reaction mechanisms!Na OEtethanolOHO

The mechanism of the following transformation will be -

Answered: HO Aldol reactions (condensation of two…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 56AP

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Draw the structures A, B and C for the reaction sequence below.
Propose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.
Draw a stepwise mechanism for the following variation of the aldol reaction, often called a nitro aldol reaction.
2 H3C H3C H C→XT OH H3C 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. base :0: OH H H 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 Instruct ns H3C heat OH H3C :0: H + H₂O H
Show how to prepare a,b-unsaturated ketone by an aldol reaction followed by dehydration of the aldol product.
2 CH3COOCH,CH3 C2H5O'K*/C2H5OH ---> CH3COCH,COOCH,CH3 [+] Hofmann elimination Clemmensen reduction Claisen condensation O Cannizzaro reaction O Aldol condensation
Provide the reagents necessary to affect each transformation
I H H3C NOC XT :0: MET H₂C base H3C 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. H OH q H3C H₂C H 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 heat H H + H₂O
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
Propose a mechanism for the following reaction.
Show a reasonable mechanism for the following reaction (Hint: Michael addition followed by intramolecular aldol condensation) ☆ NaOEt, EtOH A
The following is a key step in the synthesis of morphine involving the conversion of A to B. Draw a stepwise mechanism for this process, including an intramolecular alkylation and intramolecular aldol.A B A CHO SO2 Br N K2CO3 B N S02

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