What aldol product is formed when two molecules of butanal react together in the presence of base? draw structure ... What reagents are needed to convert this product to the following compound? HO- (+ Z isomer) [1] OH ; [2] NABH4, CH3OH [1] MCPBA; [2] OH, H20 1] (CH,),CuLi; [2] H,0 [1] CH,MgBr; [2] H,0
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- 1. Provide the mechanism of the reaction shown in the picture. 2. Explain why it cannot be done in basic conditions. 3. Why is the enol tautomer favored over the keto tautomer? Ph H3C OH H H3O+/H₂O HO H3C Ph1. Provide structures for the products and/or starting materials for the following reactions. Donor Acceptor NaOH CH₂CH₂OH heat loss of H₂O H3C mixed-aldol condensation product NaOH CH₂OH heat *) NOE EtOH #40 2) H₂O* ΕΙΟ CH₂ mixed-Claisen condensation product +HgC. H3C CHS H loss of H₂O mixed-aldol condensation product H3C людете CH3 NaOEt loss of H₂O intramolecular aldol condenstation cyclization productresource 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…
- This reaction is an example of conjugate addition of a nucleophile to an a,ẞ-unsaturated carbonyl. O CH3CH2CH2CH=CHCSCOA H₂O OH CH3CH2CH2CHCH2CSCOA Draw the two resonance structures of the enolate anion intermediate for this reaction. • Draw an R1 group in place of COA. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. ->> 90-87 O + ? ChemDoodle >e 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH3OH29) Draw all of the expected products for the following reaction. Circle the most dominant product in each reaction. 'BUOK 3 NaOEt
- 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)Draw the major product of the aldol addition reaction between two equivalents of this ketone with the conditions provided. Ignore inorganic byproducts. 1. H3O+ 2. Neutralizing work-up &60) Design a synthetic sequence/steps (multiple steps) for the following transformation (8 pts)? о ? 'OCH3 trans ? OCH3 OH trans
- 3. Provide the mechanism for the following reversible nucleophilic addition. Show all curved arrows and intermediates. cat. H+ H₂O HO OH H H 1) protonate to activate 2) nucl adds 3) deprotonate what staysRevlew Teples Referencen) 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. ノク Imail hatucP Save and CDraw the major product of the following reaction a). Remember to include the stereochemistry of the methyl groups. HCl(trace) b). HCltrace) МеОн c). -OH NaOHtrace) I|| I.