1. Aldol reactions (condensation of two aldehydes or ketones to yield a ẞ-hydroxy carbonyl) can go in reverse (B-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! H₂C. H&C. Na+ -OEt ethanol H₂C- H₂C.
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- 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 HDraw the structure of the major aldol product (prior to possible dehydration) of the following reaction. CH3 + CH3 O CH3- are CH3 H You do not have to consider stereochemistry. If no reaction occurs, draw the organic starting material. Sn [F 5% NaOH 95% aq. ethanol, 30⁰ ?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
- 4. Provide a mechanism for the following reaction. H₂SO4, H₂O HgSO4 enDraw 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ⓇHelp me
- 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 H3‑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 arrowsQ6. Propose a mechanism, using curved arrows, for the base-catalysed aldol reaction and the subsequent dehydration between furfural and cydahexanene КОН H
- Three reactions between a Grignard reagent and a carbonyl compound are given. Draw the main organic product for each reaction and indicate if H+ or H¯ is needed to complete each reaction. The starting material structures are provided in the answer fields as a starting point for your drawings. The first reaction involves a ketone. 1. CH₂MgBr 2. H+ or H™? Select Draw / |||||| C Rings O More Erase7. Propose a mechanism for the following transformation. H* `NH24) When a mixture of two different compounds both containing a hydrogens are placed under acidic or basic conditions, crossed aldol products can be formed. By either self-condensation or cross condensations. Draw the 4 aldol and 4 a.B-unsaturated ketones that can be made from the following mixed system. -OH 4 products One way to control this is by either having only one compound with a hydrogens or by reacting the desired nucleophile with lithium diisopropylamide (LDA) before addition of second carbonyl. The issue here is that this reaction stops at the aldol unless excess base is used. он LDA OH heat Show a synthetic scheme of how to use the following carbonyls to control the formation of each cross product (i.e. each as nucleophile and electrophile, two reactions). and