Lab Report # 13

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

Aldol Condensation- Synthesis of Dibenzalacetone The protocol says that, after adding in all the reactants, stir for an additional 15 minutes.  A student swirled for only 8 minutes and then, correctly, stopped and proceeded with isolating the product.  What did the student do that gave such confidence and accuracy?

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

The following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16

An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this? an acid-catalyzed aldol condensation a Fischer esterification. a Grignard reaction. a base-mediated aldol condensation

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

base H3C H OH heat H + 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. 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 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.…

Williamson Ether Synthesis of Phenacetin Background: Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.The Williamson ether synthesis is one of the simplest methods used to make ethers. The reaction is named after Alexander Williamson, who discovered the reaction in 1850. In this reaction, an alkoxide anion reacts with an alkyl halide via a substitution reaction.                         RO-Na+   +   R` – X   →   R-O-R`   +   NaX Alkoxides are strong nucleophiles that tend to react via an SN2 mechanism. As a result, the reaction works best with primary alkyl halides. In a traditional Williamson ether synthesis, the alkoxide is generated by reacting sodium hydride (NaH) with an alcohol. ROH   +   NaH    →    RO-Na+   +   H2 While this reaction is very efficient, it does pose a fire hazard, as it is possible for hydrogen gas to ignite. In this lab, the alkoxide will be created using sodium hydroxide (NaOH). This is a much safer option, eliminating a…

4) Provide the structure of the intramolecular aldol condensation/dehydration product(s) that results when diketone A below is heated in sodium hydroxide. A heptane-2,6-dione

Write the complete mechanism for the hydroxide ion catalyze reaction of cyclohexanone and 1-methylcyclohexanecarbaldehyde

Please include any cations/anions as appropriate.

Aldol condensation- Synthesis of Dibenzalacetone reaction What is this reaction classified as?

Predict the four possible Aldol condensation products and their dehydration products. KOH, H,O, A

The overall reaction produced by the aldol condensation of acetophenone and benzaldehyde is shown below. + NaOH, A Acetophenone Benzaldehyde Chalcone Which of the following steps are involved in the mechanism that leads to the formation of chalcone? он + он H OH он + Он OH + Тон Он он + + Он ОН + он