Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives aldehydes from terminal alkynes. In these reactions, the alkyne is oxidized to form an enol, which then tautomerizes toa carbonyl.Draw the structure of the enol formed in the conversion of 1-hexyne to hexanal.Click and drag to start drawing astructure.

Answered: Alkynes undergo hydroboration to give…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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The following compound undergoes an intramolecular reaction to form ethene and a product with a five-membered ring. Identify the product and the catalyst used to carry out the reaction.
An alkene is treated with OsO4 followed by H2O2. When the resulting diol is treated with HIO4, the only product obtained is an unsubstituted cyclic ketone with molecular formula C6H10O. What is the structure of the alkene?
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.
Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.
Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?
Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.
Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.50 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%yield? Express your answer in grams to three significant figures.
Acetal derivatives of aldehydes and ketones are prepared by an acid-catalyzed dehydration reaction with alcohols or diols. Using more pictures than words, draw a reaction and a mechanism that shows the formation of acetal.
The SN2 reaction is an example of a nucleophilic substitution reaction. Draw the structure of the two reactants and the mechanism of the reaction. The reaction is 1-bromo-3-ethylpentane reacts with cyclohexanol under basic conditions.
4) Give an example of an enol which would tautomerize into a) an aldehyde and b) a ketone.
Chrysanthemic acid occurs as a mixture of esters in flowers of the chrysanthemum (pyrethrum) family. Reduction of chrysanthemic acid to its alcohol followed by conversion of the alcohol to its tosylate gives chrysanthemyl tosylate. Solvolysis alcohols. of the tosylate gives a mixture of artemesia and yomogi HO НО Chrysanthemic acid Chrysanthemyl alcohol OH TsO DMSO Chrysanthemyl tosylate Artemesia alcohol Yomogi alcohol Propose a mechanism for the formation of these alcohols from chrysanthemyl tosylate.

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