Organic Chemistry
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Using the given alkyl bromide, synthesize the product shown on the right using the minimum number of steps.
Using only molecules containing three carbons or fewer, synthesize the molecule below.
Using the given initial compound, synthesize the molecule shown on the right using the minimum number of steps necessary as indicated below.
Synthesize the molecule below using the starting material, any necessary inorganic reagents, and any carbon-containing compounds with a maximum of two carbons.
Suggest a synthesis for the following compound starting with any alcohol that contains a maximum of five carbons as the organic material. Ignore stereochemistry.
Propose a method to synthesize the following compound starting with any alcohol containing a maximum of 6 carbons as the organic material.
Given the following starting materials, propose a synthesis to transform them into the target compound. Use any additional reagents needed. (Ignore stereochemistry).
Provide the structures of compounds I through VI given the following information: I (C8H13Br) reacts with magnesium in ether to produce II (C8H13MgBr), which then reacts with D2O to give 3-isopropylcyclopent-1-ene with a deuterium atom on the end of the isopropyl group (III). II reacts with butan-2-one (C4H8O) followed by acid work-up, and produces IV (C11H20O). IV is then heated with concentrated H2SO4 to produce V (C11H18), which then reacts with two equivalents of Br2 to give VI (C11H14Br4). V undergoes hydrogenation with excess H2 and Pt catalyst to produce (3-methylpentan-2-yl)cyclopentane. (Ignore stereochemistry)
Using any inorganic reagents, propose a synthesis for (±)-decane-5,6-diol using acetylene and 1-bromobutane as the starting organic compounds.
We often repeat the same steps when performing synthetic analysis to produce the desired product. To see this in action, use the alkynide synthesis to determine how the following aldehyde is produced, starting with an organic molecule with three or fewer carbons.
Provide a synthetic scheme to form the product from the given starting molecule. Include a protecting group in the scheme.
Propose a mechanism for each of the following:
(i) Two molecules of 2-methylprop-1-ene + HA (general acid representation) → 2,4,4-trimethylpent-2-ene
(ii) Polymerization of phenylethylene or styrene to form polystyrene through the Cl3Al−OH2 catalyst [up to the tetramer formation]
Develop a synthesis for oct-4-yn-3-ol. Use acetylene as the starting material and other organic compounds containing no more than three carbon atoms.
Develop a synthesis for cis-1-isobutyl-2-isopentylcyclopropane. Use acetylene as the starting material and other organic compounds containing no more than five carbon atoms.
Given 1,2,5-trimethylcyclohept-1-ene as the starting material, provide a step-by-step process to synthesize the compound below. If a step forms a chiral center, assume the reaction produces a racemic mixture.
Draw the mechanism that explains the difference in regiochemistry between the reactions below. (Ignore stereochemistry)
Propose the synthesis that would accomplish the given transformation.
2-methylcyclopentan-1-ol → 1-bromo-1-methylcyclopentane
Identify the steps to show the synthesis of the cyclopropane from the bromoalkane below.
Propose a multistep synthesis showing how can the target molecule be prepared from the starting material.
Identify structures (I)–(V).
Given 5,6-dimethylcyclooct-1-yne as the starting molecule, suggest a method to synthesize the molecule shown below. Disregard stereochemistry.
Design a multistep synthesis to produce the following target molecule using the given starting material.
Compound A with the molecular formula C7H12 has an ethyl group and a cyclic ring. It reacts with one equivalent of H2, Pd/C to produce B. The hydroboration-oxidation reaction of A produces a pair of enantiomers, C and D. After the ozonolysis of A, a reaction with dimethyl sulfide produces E with the chemical formula C7H12O2, which contains one aldehyde and one ketone functional group. Draw the structures for A–E.
Start with cyclopentene and write the possible reaction sequence to prepare the compound given below.
Determine the reagents required to perform the following reaction.
Provide the reagents that will be required to carry out the given reaction.
For each reaction in the sequence given below, write the proper reagent:
How can 1-ethylcyclohexanol be prepared, starting with ethynylcyclohexane? Write the structure of the second alcohol that would also be obtained as a product.
Provide appropriate reagents to carry out each of the following reactions.
Using but-1-ene as your starting material, show how the following compounds can be synthesized.(i) but-2-yne(ii) butan-2-one(iii) butanal
Using but-1-ene as your starting material, show how the following compounds can be synthesized.(i) propanoic acid(ii) propanal(iii) hept-4-yn-3-ol
Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.trans-but-2-ene → but-2-yne
Provide the missing products, in each step of the given synthesis. Include any important stereochemistry.
Provide the missing products in each step of the given synthesis and show any important stereochemistry.
Propose a synthesis plan for the following compound. You can use any alkenes or cycloalkenes that contain no more than six carbon atoms as the starting material.
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.
Provide the missing products of each reaction in the following synthesis.
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.
Starting with cyclopentanone, synthesize the following compounds:
Draw the structures of (1) through (5) in the following scheme:
Propose a synthetic pathway to synthesize the following compounds starting from cyclopentanol and any necessary reagents and solvents.
Draw the structures of the missing compounds A through C in the following synthesis.
Propose a synthetic scheme that includes protecting groups in order to produce the desired product from the given starting material.
Starting from 1-bromo-2,3,4,5,6-pentamethylbenzene and any other reagents and solvents needed, show how to synthesize (E)-3-(2,3,4,5,6-pentamethylphenyl)prop-2-en-1-ol.
Using the Grignard reaction, prepare 1-cyclopentylpropan-1-ol enantiomers from bromocyclopentane and any other necessary reagents.
Using 3,4-dimethylcyclopentan-1-one as the starting material, provide a synthetic scheme to produce the given compound.
Show how the compound shown below can be prepared starting with cyclopentene.
Show how the product can be prepared from the given starting material. Use any carbon source with no more than three carbons and any necessary inorganic reagents and catalysts.
Which of the following reactions does not yield an alcohol?
a. b.
c. d.
For the synthesis below, start with chlorocyclopentane and predict the structures of products 1 through 5.