HO Aldol reactions (condensation of two aldehydes or ketones to yield a ẞ-hydroxy carbonyl) can go in reverse (ẞ-hydroxy carbonyl to two aldehyde/ketones, a retro-aldol). Propose mechanisms for the following two transformations, using both intra-molecular aldol and a retro-aldol reactions. Be sure to follow the rules we have discussed for writing reaction mechanisms! Na OEt ethanol OH O
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- 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 the product formed when each dicarbonyl compound undergoes an intramolecular aldol reaction followed by dehydration, when possible.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
- 2 CH3COOCH,CH3 C2H5O'K*/C2H5OH ---> CH3COCH,COOCH,CH3 [+] Hofmann elimination Clemmensen reduction Claisen condensation O Cannizzaro reaction O Aldol condensationMatch the following transformations (Organic I and II) with the appropriate reagents.Draw the structure of the major aldol product (prior to possible dehydration) of the following reaction. CH3 CH3 H dilute NaOH 95% aq. ethanol, 0-5⁰ You do not have to consider stereochemistry. • If no reaction occurs, draw the organic starting material. O-Sn [F ? ChemDoodleⓇ
- 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 + H₂Obase 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) Cinnamaldehyde is used in artificial cinnamon flavoring. Show how cinnamaldehydeis synthesized by a crossed aldol condensation followed by dehydration.H CHcinnamaldehyde C COH(b) Adding acetophenone slowly to a cold solution of LDA produces the enolate of acetophenone; but adding LDA slowly to a cold solution of acetophenone produces acondensation product. Show the reactions happening in each case, and explain why weobserve such different results
- 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 S023‑Methylbutanal undergoes an aldol reaction to form 3‑hydroxy‑2‑isopropyl‑5‑methylhexanal. Complete the mechanism for the reaction by adding missing atoms, bonds, charges, nonbonding electrons, and curved arrowsDraw the product formed when each dicarbonyl compound undergoes anintramolecular aldol reaction followed by dehydration, when possible.