Organic Chemistry
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Predict the product(s) formed when the given alkene reacts with HBr and H2O2.
Determine the product(s) formed by the reaction of the given alkene with (1) Hg(OAc)2, H2O, followed by (2) NaBH4.
The following acid-catalyzed reaction transforms grandisol into a bicyclic alcohol. Determine the mechanism for the reaction described.
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.
Consider the following conversion of compound A to B:
What is the mechanism for the reverse reaction, which is the acid-catalyzed conversion of compound B to A? What makes this mechanism correct?
The given alkylation reaction of the acetylide would be unsuccessful and would only produce the original substrate. Explain why the reaction is unsuccessful.
Determine the reagents needed to carry out the given reaction.
Predict the products you would get when the following alkene reacts via acid-catalyzed hydration and oxymercuration–reduction.
Outline the steps and reagents used to synthesize the vicinal diol below beginning with only one unsaturated aliphatic hydrocarbon containing four carbons.
Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. Suggest an alkene and a reagent that would give the product below. Note: The alkene should not undergo rearrangement.
Provide the alkyne and the alkyl halide used for synthesizing the alkyne below. [There are two possible answers.]
Repeating same series of steps is done when performing synthesis analysis to produce the desired product. To see this in action, the alkynide synthesis below determines how the following aldehyde is created, starting with a terminal alkene of five carbons. Is the synthesis correct?
For the following alkyne, draw the product(s) when it reacts with Cl2 (2 equiv.).
In general, alkenes are more reactive to electrophiles than their corresponding alkynes. However, this reactivity difference is much greater and more evident in the addition of HBr as compared to the addition of Br2. Explain why this is the case.
The compounds α-pinene and β-pinene are just some of the terpenes that can be produced from geranyl diphosphate. Suggest an arrow-pushing mechanism for the conversion of geranyl diphosphate to β-pinene. Assume that an enzyme active site has an abundance of the acid/base needed.
Predict the product(s) if the following alkene undergoes acid-catalyzed hydration and oxymercuration–reduction.
Predict the product(s) that would result when the alkene below undergoes the following conditions: acid-catalyzed hydration and oxymercuration–reduction.
Give the synthesis of the product shown using the provided reactant, any inorganic reagents, and any organic molecule with less than four carbons.
Give the reaction sequence showing how the following product can be prepared from the starting material.
Draw the stereoisomeric products that would form when pent-2-yne reacts with the following reagents.
1) H2/Lindlar catalyst
2) Br2/CH2Cl2
Which of the following stereoisomeric products form when pent-2-yne reacts with the following reagents?
1) Na/NH3(liq), −78 °C
What reagents would be able to synthesize the following compound via olefin metathesis?
Draw the products that will form when the compounds below react with CH3CH2CH2CH2C≡C:–Na+ followed by H2O workup.
(i) cyclopentanone
(ii) CH3CH2CHO
Consider the following triolefin reaction using a metal alkylidene catalyst:
What is its mechanism?
What is the product of the metathesis reaction when it is catalyzed using Schrock or Grubbs catalyst?
How could the molecule shown below be synthesized using 2,3-dimethylbut-1-ene as the initial molecule?
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]
The majority of alkene synthesis results in the formation of the more stable trans isomer. Provide a reaction scheme for synthesizing henicos-7-ene from acetylene and other compounds that specifically produce the cis isomer.
Provide the reaction scheme that shows the inorganic reagents necessary to convert acetylene and 1-bromo-3-ethylpentane into meso-3,10-diethyldodecane-6,7-diol.
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.
The addition of an acetylide ion to a carbonyl group is used in the synthesis of 3-ethynylhept-1-en-3-ol. Propose a synthesis using acetylene and a carbonyl compound as the starting materials. (Ignore stereochemistry)
Draw the structure of the predicted product between the phenylethyn-1-ide ion and each of the compounds listed below.
a) 1-chloropropane
b) 1-chloro-3-methylbutane
c) propionaldehyde followed by water workup
Provide the synthetic step(s) required to complete the following conversion. (Ignore stereochemistry)
1-methylcyclohexanol → 2-bromo-1-methylcyclohexanol
Using 1-methylcyclohex-1-ene as the starting material, outline the step-by-step process for synthesizing the compound shown below. If a step forms a chiral center, assume the reaction results in a racemic mixture.
Draw the expected products from the following metathesis reaction:
Provide the expected products from the following metathesis reaction:
Draw the smaller molecules used to assemble the following alkenes through olefin metathesis. (Use the smallest alkenes needed)