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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- 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, C7H8OOne 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?
- Name 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 CH3An 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.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 4
- 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 %3DFollowing 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.)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
- 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 CH₂OHCCH 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*Write down the common (not IUPAC) names of the organic molecules that would be released if this molecule were hydrolyzed: CH,—O—C—(CH2)—CH=CH-CH,—CH=CH—(CH2) — CH3 CH-0- -(CH2)–CH=CH(CH2)CH3 O CH,—O-C=(CH2)=CH=CH(CH2)—CH3 Separate each name with a comma and a space. You will find useful information in the ALEKS Data resource. type your answer...