Organic Chemistry
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The position of triple bonds in alkynes can be determined through oxidative cleavages. An unknown alkyne gives dodecanedioic acid as shown below. Propose the structure of this alkyne.
The positions of triple bonds in alkynes can be determined through oxidative cleavage. An unknown alkyne gives malonic acid and two equivalents of carbon dioxide, as shown below. Propose the structure of this alkyne.
Using cyclononyne as the starting molecule, propose a method to synthesize cyclononane-1,2-dione.
Given cyclodecyne as the starting molecule, suggest a method to synthesize the molecule shown below.
Predict the product(s) obtained when 2-methylnon-4-yne reacts with the following reagents:
(i) KMnO4, H2O, neutral
(ii) KMnO4, KOH, H2O, heat, then H+, H2O
Provide the product(s) obtained when cycloheptyne reacts with the following reagents:
The molecular formula of compound X is C7H10. Compound X undergoes catalytic hydrogenation to produce cycloheptane. Compound X undergoes ozonolysis, followed by reduction with dimethyl sulfide, to produce heptanedioic acid. What is the structure of compound X as described?
What plausible organic products are formed when hept-1-yne is treated with:
i) Diluted and neutral KMnO4
ii) Warm and basic KMnO4, then diluted acid
Determine the plausible products when hept-2-yne is treated with:
i) Diluted and neutral KMnO4.
ii) Warm basic KMnO4, then with diluted HCl.
Determine the plausible products when hept-3-yne is treated with:
i) Diluted, neutral KMnO4
ii) Warm and basic KMnO4, then HCl acid
Provide a synthetic scheme for the following carboxylic acid synthesis.
(i) 2,7-dimethyloct-4-yne → 3-methylbutanoic acid
(ii) cis-cyclotetradecene → tetradecanedioic acid
An unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclopentane when it is treated with hydrogen gas in the presence of a platinum catalyst. The following products are obtained when X is treated with an excess of ozone, followed by dimethyl sulfide and water.
Propose a structure for the unknown compound X. Is there any uncertainty in the structure that you proposed?
Determine the identity of products obtained in the reaction of but-1-yne with each of the reagents shown below.(i) dilute, cold solution of KMnO4(ii) concentrated warm solution of KMnO4 and NaOH, then HCl(iii) Na in liquid NH3