Organic Chemistry
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Show the ketone that forms when each alkyne undergoes an oxymercuration reaction.
(a) 5-methylhept-1-yne
(b) 1,8-dicyclopentyloct-4-yne
Acid-catalyzed hydration of alkynes in the presence of HgSO4 produces ketones as products. Identify one possible alkyne which deviates from this rule and produces an aldehyde instead.
Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.but-1-yne → butan-2-one
Oxymercuration-reduction is an excellent method for obtaining single compounds from the hydration of symmetrical internal or terminal alkynes. Draw the product of the oxymercuration-reduction reaction for the following compound:
1-pentyne
Oxymercuration-reduction is an excellent method for obtaining single compounds from the hydration of symmetrical internal or terminal alkynes. Draw the products of the oxymercuration-reduction reaction for the following compound:
2-pentyne
Show how hex-1-yne can be converted to hexanal. Provide any necessary reagents.
Show how 1-bromobutane can be converted to hexanal. Provide any necessary reagents.
Identify the reagent required to complete the syntheses shown below.
Consider the following aldehyde:
Is it possible to synthesize the aldehyde from an alkyne with a yield greater than 50%? If so, provide the synthetic scheme.
Provide the best alkyne to use to produce each of the following ketones.
Provide the best alkyne to use for the synthesis of the ketone below.
Propose a way to synthesize the product shown using the provided starting molecule, any inorganic reagents, and any organic molecule with only 4 carbons or fewer.
Provide the product/s when 2-methyloct-3-yne goes through acid-catalyzed hydration.
Hydration of an asymmetrical internal alkyne via oxymercuration gives two different compounds. Predict the products that could form from the hydration of the alkyne below.
The reaction of hex-2-yne with mercuric sulfate in dilute sulfuric acid produces two ketones. Propose a plausible mechanism that leads to the two ketone products. [Note: Do not forget to show lone pairs.]
Hydration of symmetrical or terminal alkynes via oxymercuration produces a single compound with a high yield. What is the product of hydration of the following alkyne?
Provide the reagents needed to perform the following reaction.
Identify the two alkynes that can be used in the synthesis of the following ketone, and determine if it can be synthesized in a high yield utilizing any of the two reactions. If not, draw all the possible products.
Determine the major product formed when 3-hexyne reacts with H2O, aqueous H2SO4, and HgSO4.
How is pentan-2-one made from a hydrocarbon with the same number of carbon atoms as the expected product?