Each of these aldol products comes from an enolate donor and a carbonyl acceptor. DONOR АССЕРТOR 1. CHO 2. 3. 4. 5. Write the donor and acceptor from a choice below. e.g if you thought for #2 the Donor was A and the acceptor was B, you would write A, B CHO cote
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- Draw the major product of the aldol condensation reaction between two equivalents of this aldehyde with the conditions provided. Ignore inorganic byproducts. I 1 1. H30*, heat H 2. Neutralizing work-up Drawingresource from Cengage Learning - Google Chrome ssignment/takeCovalentActivity.do?locator=assignment-take e by the Aldol Condensation (References) OH base + H,0 heat H. 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. In the mixed aldol reaction, the best results are obtained when one of the partners does not have an a-hydrogen. It cannot form an enolate anion and can therefore not undergo self-reaction. The enolizable aldehyde is added slowly to a basic solution of the first aldehyde so that the mixed product is preferentially formed. Under reaction conditions slightly more vigorous…2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible). NaOH/H₂O A CH3 a. b. C. H₂C Draw the structure for the enolate ion (show both of the relevant resonance structures). Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)
- Draw structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol or enone below. & • You do not have to consider stereochemistry. ● Draw the enolate ion in its carbanion form. ● Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple reactants using the + sign from the drop-down menu. / MILL ? ChemDoodle Ⓡ YThis reaction shows that an aldol-type reaction can be performed with a deprotonated imine as the nucleophile. On hydrolysis, the product is the normal B-hydroxycarbonyl compound. Notice that LDA is used H3C N. 1. LDA Но ? as the base instead of HO¯. H3C H. H. (a) Explain why HO¯ cannot be used as a base for this 2. reaction. (b) Provide a detailed mechanism for this reaction, including the structure of the intermediate species not shown.Write structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol below. ОН You do not have to consider stereochemistry. • Draw the enolate nucleophile in its carbanion form. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple reactants using the + sign from the drop-down menu.
- In a mixed aldol condensation with unknown aldehydes and ketones experiment, some aldol condensation reactions need to be heated for the dehydration step to occur. Explain why that was not necessary for the reactions carried out in this experiment? [Hint: what makes the product especially stable?]. This experiment used ethanol, acetic acid, sodium hydroxide, cyclohexanone and 4- methoxybenzaldehyde.2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible (since both of the reactants possess an acidic alpha proton). a. b. C. CH3 + H₂C H NaOH/H₂O Draw the structures for the two possible enolate ions. Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)Write structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol below. OH H You do not have to consider stereochemistry. • Draw the enolate nucleophile in its carbanion form. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the sign from the drop-down menu. ? ChemDoodle Sn [F
- ne by the Aldol Condensation [References] Draw structures for the carbonyl electrophile and enolate nucleophile that react to give the enone below. H. • You do not have to consider stereochemistry. • Draw the enolate ion in its carbanion form. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu. C opy asteIn an aldol condensation where cyclopentanone reacts 1:1 with Ortho- methoxybenzaldehyde. How many signals would appear in an HNMR for the condensation product? а. 9. o b. 7 С. 10 d. 11 O . 8Claisen-Schmidt reactions Џон + 10 5. An aldol reaction involving an aldehyde and a ketone are Claisen-Schmidt reactions. They are mechanistically identical to normal aldol reactions (i.e. involving two aldehydes). Write the is bazzo mechanism for the NaOH-catalyzed Claisen-Schmidt reaction of butanone with benzaldehyde. novedgoteus? Jon ni abubong noitibbs loble ils off W des 101 áslumot slusalom s/hw bns G H no & H 2 H I fruf OH OH ip H 2 H HoD year Hensbrio) - S08 M3HO 니 6. Claisen-Schmidt reactions (and aldol reactions) undergo dehydration (i.e. the condensation step) when heated in basic or acidic solution. Write the mechanism for dehydration of the Claisen-Schmidt product in problem 5. OH -H₂O