Organic Chemistry
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Show the necessary reagents 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.
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.
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
Alcohol X (C6H12O) was oxidized to an aldehyde using NaOCl and CH3COOH at 0 °C. When this alcohol was distilled in H2SO4, two alkenes were formed. The major alkene product is 1-methylcyclopent-1-ene. The minor alkene product formed the starting alcohol when reacted with 1. BH3/THF, 2. H2O2, HO−, and H2O. What is the identity of alcohol X?
Draw the amides that would be converted to the following amines when reacted with 1. LiAlH4, 2. H2O.
(i) tripropylamine
(ii) dipropylamine
(iii) propan-1-amine
(iv) N-benzylethanamine
Deuterium-containing compounds (D = 2H) are helpful for kinetic and metabolic research with novel drugs. LiAlD4, reagent LiAlH4's counterpart in reactivity, is one approach to introduce deuterium. Using LiAlD4 and D2O as your sources of deuterium and other non-deuterated starting materials you choose, demonstrate how to create this deuterium-labeled molecule, CH3CH2CD2OH.
The steps involved in hydride reduction of ester are as follows.
Identify the step(s) in which the ester compound is(are) particularly reduced. (Hint: Count the number of bonds to oxygen)
Show how to synthesize the compound below from an ester with fewer than 10 carbon atoms. You can use any additional reagents.
Show the step(s) on how to produce the compound shown below from an ester with less than ten carbon atoms. You can use any reagents you need.
Demonstrate how the following alcohol can be produced by reducing a suitable carbonyl compound.
Pentanoyl chloride is reduced by lithium aluminum hydride. Propose a mechanism for this reduction.
Show the steps required to produce the compound shown below. Use an ester with less than 7 carbons as the starting material and any other reagents required.
What carbonyl compounds and appropriate reducing agents could be used to synthesize the alcohols given below?
(a) 1-phenylethan-1-ol
(b)
How would you synthesize the given 1° alcohol using each of the following starting materials?
(a) An eight-carbon aldehyde
(b) A carboxylic acid
Predict the product likely to form when the given compound reacts with NaBH4 in the presence of methanol as solvent.
Predict the product(s) likely to form when the following compound reacts with LiAlH4 followed by hydrolysis.
What product would you expect from the following reaction after an acidic workup?
Predict the product likely to form when the following compound reacts with LiAlH4 followed by hydrolysis. Ignore stereochemistry.
Show the product that would be formed in each of the following reactions.
When LiAlH4 reduces 3-isopropylcyclopentanone, it yields 70% cis-3-isopropylcylopentanol and 30% trans-3-isopropylcylopentanol. Show how the cis-isomer is formed to explain why the cis-isomer is preferred.
Consider the following synthesis:
Predict the products formed in each step. Assume that each reactant is added in excess to facilitate every possible reaction.
Predict the product likely to form when the following compound reacts with NaBH4 in methanol.
Predict the product likely to form when the given compound reacts with NaBH4 in methanol.
What organic products would be formed in the below-given reactions? [Ignore stereochemistry]
Show how you would accomplish the given synthesis. Recommend both a chromium-based and a chromium-free oxidizing agent.
Propose the synthesis of the following, starting with an alcohol.
Illustrate how to obtain the following deuterium-labeled compound, using LiAlD4 and D2O as the sources of deuterium, and any non-deuterated starting materials:
CH3CH2CD2OD
NaBH4, NaBD4, and D2O are readily available commercially. Show how the following labeled compound can be synthesized using the given starting material.
Suggest the best reagents to use for the conversion below.
NaBH4 is a weaker reducing agent than LiAlH4. It can be used to selectively reduce aldehydes or ketones in the presence of esters, such as in the selective reduction of the ketone functional group of methyl 3-oxobutanoate. Write the appropriate Lewis structure for NaBH4.
For each reaction shown below, determine the product formed and identify if the reaction is an oxidation or a reduction.
What is the correct mechanism for the reaction shown below?
What is the final major product of the reaction sequence shown below?
Propose a synthetic approach to produce each of the given compounds using suitable carboxylic acids or their derivatives.
Provide a synthetic pathway to produce the following compound using the given starting material.