Organic Chemistry
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Draw the alcohol(s) that would produce the given ketone upon oxidation.
Show the synthesis of the following carbonyl compound using the dihydroxylation reaction of an alkene followed by the treatment with periodic acid.
Suggest a synthesis of the following carbonyl compounds using the dihydroxylation reaction of an alkene followed by the treatment with metaperiodic acid.
Show how you could accomplish the following conversion.
Write the necessary reagents for the following reaction.
Show how would you convert the following compound into the given product.
Show the necessary reagents required to produce the following compound using the given starting material.
What reagents are required to produce the following compound using the given starting material?
Which reagent could be used to carry out the following reaction?
Identify the missing products.
What would be the product of the following reaction? Ignore stereoisomers.
Provide suitable reagents to carry out the following reaction.
Provide suitable reagents for the reduction of the following compound.
Which reducing agent could be used to carry out the following reaction?
Provide appropriate reagents to carry out the following reaction.
Provide the missing products of each reaction in the following synthesis.
Suggest the most suitable reagents for the following oxidation reactions.
a. propan-1-ol → propanalb. propan-2-ol → 2-propanonec. prop-2-en-1-ol → prop-2-enal
For each reaction, suggest two reagents: a chromium-based reagent and a non-chromium-based reagent.
Devise an approach for the synthesis of cis-1,2-cyclohexandiol. You can start with cyclohexanone, any reagent that contains four carbon atoms or less, and any required reagent or solvent.
Devise an approach for the synthesis of the following molecule.
You can start with cyclohexanone, any reagent that contains four carbon atoms or less, and any required reagent or solvent.
How can 3-methylbutan-1-ol be synthesized by reducing a carbonyl compound?
How can 3-methylpentan-2-ol be synthesized by reducing a carbonyl compound?
Deuterated organic compounds are useful in kinetic studies of chemical reactions and in metabolic studies of pharmaceutical drugs. Reducing a carbonyl compound using a deuterated reducing agent, such as NaBD4, is one of the many ways of producing deuterated organic compounds. Using NaBD4 and D2O as sources of deuterium, devise a plan for the synthesis of the following compound.
C6H5CHDOD
How can the following transformation be achieved? You can use any reagents as required.
Identify which carbonyl compound and the reducing agent can be used to synthesize benzyl alcohol.
Identify which carbonyl compound and the reducing agent can be used to synthesize 1-phenylethan-1-ol.
Determine the major product of each reaction below.a. 1-methylcyclopentan-1-ol + H2SO4, heatb. major product of a. + H2, Pt
Provide the final products of the reaction in which the following compound is treated with NaBH4 in methanol.a. CH3-(CH2)2-CHO
Provide the final products of the reaction in which the following compound is treated with NaBH4 in methanol.
a. Ph-CH2-COOH
Provide the final products of the reaction in which the following compound is treated with LiAlH4 in methanol followed by hydrolysis.a. CH3-(CH2)2-CHO
Provide the final products of the reaction in which the following compound is treated with LiAlH4 in methanol followed by hydrolysis.a. Ph-CH2-COOH
Complete the following chemical equation with suitable chemical reagents and solvent.
Aldehydes are reduced more rapidly than ketones by a mild reducing agent Sodium triacetoxyborohydride, NaBH(OAc)3. Even in the presence of ketone, NaBH(OAc)3 preferentially reduces aldehyde, as shown in the following reaction.
Propose the reaction mechanism underlying this selective reduction.
Complete the following chemical equation with suitable chemical reagents and solvents.
Show the expected major product for the reaction given below.
Propose a synthetic approach for the following conversion using any needed reagents.
Extraction of peanuts gives triolein in good quantities. Its IR spectrum shows a strong peak at 1722 cm-1. It is a liquid with a melting point of 5 °C. When it is hydrolyzed in a basic medium, 1 equivalent of glycerol and 3 equivalents of oleic acid are obtained.a. Draw the structures of triolein.b. Show the structures of its products when treated with lithium aluminum hydride, followed by aqueous hydrolysis.
Determine the product formed when the following esters react with DIBAl-H. For a reaction sequence utilizing this reaction, is there a need to convert from one ester to another?
What is the product formed in the reduction reaction given below?
Draw the structure of the product(s) formed in the reduction reaction shown below:
Give the reaction mechanism when pivalic anhydride is reduced using lithium aluminum hydride.
Determine the final product formed in the sequence of reactions shown below.
Determine the product formed from the following reduction reaction.
What is the product formed in this reduction reaction?
What reagent should be used to selectively reduce the alkene while preserving the carboxylic acid in the given reaction?
Two esters are reduced to ethanol and 2-methylpropan-1-ol by LiAlH4 (followed by adding aqueous acid). Draw the structures of these two esters.
Provide the alcohols produced by the reduction of each of the compounds below with NaBH4.
i. 2-ethylbutanal
ii. cyclopentanone
Give the alcohols produced by the reduction of each of the compounds below with NaBH4.
i. 3,4-dimethylcyclopentanone
ii. benzophenone
Consider the compounds below. Provide the organic products if the compounds are reacted with LiAlH4, followed by adding a dilute acid.
i. butyl propionate
ii. 4-ethylbenzoic acid
Consider the compounds below. Provide the organic products if the compounds are reacted with LiAlH4 followed by dilute acid.
i. propyl benzoate
ii. 5-methylhexanoic acid
Starting with cyclopentanone, synthesize the following compounds: