Alkyne anions react with the carbonyl groups of aldehydes and ketones to form alkynyl alcohols, as illustrated by the following sequence. HCI CH,C=C Na* + H-C-H [CH,C=C-CH,O Na*] H,O → CH,C=C-CH,OH Propose a mechanism for the formation of the bracketed compound, using curved arrows to show the flow of electron pairs in the course of the reaction.
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- The action of heating one mole of water (containing a trace of acid catalyst) on one mole of compound Y produces one mole of CH,COOH and one mole of CH, CH,NH, The structure of Y is: Select one: O CHCNCCH, CH,CH,NHCH,CH, OH CH CHNHCH,CH, O CHCH,CNHCH; O CH;CH NHÖCH;Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.Draw structures of compounds that fit the following descriptions: a) An , unsaturated ketone, C9H8O b) An diketone c) An aromatic ketone, C9H10O d) A diene aldehyde, C7H8O
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?What is the major organic product obtained from the following reaction? OH OH H,0 CH;CH,CH,CH,C=CH OH HgSO, H,SO, ÓH O 1 O 2 O 3 O 4Name the following aldehydes and ketones according to IUPAC rules: lel CH3ČCH,CH,CH,ČCH,CH3 (b) CH2CH2CHO ta) CH3CH2CCHCH3 tel Id) ÇH3 H CH3CH=CHCH2CH;CH "сно CH3
- What is the correct assignment of the names of the following ketones? H;C CH3 CH3 1 2 O 1 = acetone; 2 = phenol; 3 = benzaldehyde 1 = acetone; 2 = acetophenone; 3 = benzophenone %3D %3D O 1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone %3D O 1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde %3D %3DAn important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.Rank the following alcohols in order of increasing ease of acid-catalyzed dehydration. Provide the structure of the dehydration product (alkene) from each alcohol. OH OH 3 1 a OH
- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Oblivon HO Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains al- kyne and hydroxyl functional groups.)CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*Classify each chemical reaction as an addition, elimination, isomerization, or nucleophilic substitution. -- H3C-C-O-CH3 + H₂O 11 H3C-C-OH+H3C-OH H₂C=C-COO™ O-P=O OH + H₂O OH ī H H₂C-C-Coo O O-P=O I OH COO™ HC-OH CH₂ COO™ HC=0 H-C-OH CH₂OH COO™ CH || + H₂O CH COO™ CH₂OH C=O I CH₂OH