Organic Chemistry
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Starting with 3-cyclohexylpropanamide, two different pathways lead to the same ketone product. Draw the ketone generated by the pathways shown below.
On the basis of stereochemistry, explain why the following reaction does not occur via the SN2 mechanism.
Oxidation of phenols can be used in tandem with other reactions to form new carbon-carbon bonds. Identify the product for the synthesis below.
Identify the main product of the reaction shown below.
Suggest a set of reagents involving a cuprate reagent for the synthesis below.
Choose the reagent and a reactant pair that could be used to form the compound below.
Suggest a synthetic scheme, involving a Grignard reagent with a protecting group, to bring about the transformation shown.
Determine the product of the reaction given below.
Propose a scheme to synthesize the molecule on the right starting with the molecule on the left.
Propose a synthesis of the following molecule starting with the initial molecules shown, using a cuprate cross-coupling reaction.
Predict the products formed from the reactions shown below.
Determine the product that will be obtained in this reaction.
The Reformatsky reaction refers to the addition of an aldehyde or ketone to a carbonyl group using an organozinc reagent. The organozinc reagent exhibits lower reactivity compared to a Grignard reagent, so it does not undergo nucleophilic addition to the ester group. The reagent is prepared by treating an α-bromo ester with zinc.
Provide a synthetic scheme that uses the Reformatsky reaction to synthesize the compound shown below.
Determine the alcohol that will form when 2,2-dimethyloxirane reacts with diallylcuprate (CH2=CH–CH2)2CuLi followed by acidic work-up.
Give a reaction scheme that uses bromocyclopentane as a starting material to produce the following compound:
Give the products of the given reactions while considering stereochemistry.
Ignoring stereochemistry, give the products when 3,5-dimethylcyclopent-2-en-1-one is reacted with the given sets of reagents:
i) CH3MgBr followed by H3O+
ii) (CH3)2CuLi followed by H3O+
Propose the synthesis of cyclohexyl isobutyl ketone from an alkyl halide containing six (6) carbon atoms or less.
Propose the synthesis that would accomplish the given transformation using an organolithium reagent.
4-methylpentanoic acid → 7-methyloctan-4-one
What products are expected in the acid chloride reactions given below?
Suggest a synthesis that would accomplish the given transformation using an organolithium reagent.
3-phenylpropanoic acid → 4,4-dimethyl-1-phenylpentan-3-one
Show how to produce the compound shown below from an ester with less than nine carbon atoms. You can use any reagents you need.
Ignoring stereochemistry, draw the structures of (i) through (v).
Show how you would synthesize 1-ethylcyclopentan-1-ol using methylenecyclopentane and any other reagents required.
What is the expected product of the reactions shown below after hydrolysis?
(i)
(ii)
Determine the products of the reactions below:
Provide the reagents needed to accomplish the conversion given below using an organolithium reagent.
Give the reagents needed to accomplish the conversion given below using an organolithium reagent.
Provide the expected organic products from the following reaction.
Draw the expected major product for the reaction shown below:
Propose a reaction pathway for the following synthesis. If the reaction involves oxidation reactions, provide both a chromium reagent and a chromium-free reagent.
(1) cyclohexanol → 1-methylcyclohexanol (two steps)
(2) cyclohexylmethanol → 1-cyclohexylethanol (two steps)
Show how you would synthesize the following compound:
Start with cyclohexanol as the starting material, and use an appropriate alcohol containing four carbon atoms or fewer, and any required reagents or solvents.
Provide a synthetic pathway for the below-given compound using starting materials that contain seven or fewer carbon atoms. [Ignore stereochemistry]
Provide the synthetic steps to produce the following compound:
Starting with an alcohol with four or fewer carbon atoms and cyclopropanecarbaldehyde, show how you would synthesize the following molecule:
What are the major products in the metathesis reaction of the alkene shown below?
Predict the product in the Heck reaction given below.
What unsaturated polymer is formed from the ring-opening metathesis of the compound given below?
Which diene goes through ring-closing metathesis to form the compound shown below?
What are the major products in the metathesis reaction of the alkene given below?
Draw the products formed in the metathesis of the alkyne given below.
What are the major products obtained in the ring-closing metathesis of the compound given below?
What starting material undergoes the ring-closing metathesis to produce the following compound?
The plant metabolite nonadec-1-ene is a positional isomer of nonadec-7-ene. How could you synthesize (Z)-nonadec-7-ene using 2 molecules of 1-bromopropane as one of the starting materials?
For the given epoxide, its reaction with an organolithium reagent and subsequent treatment with acid would exclusively generate the initial epoxy alcohol compound. (I) What is the reason for this outcome? (II) What conditions can be altered to the reaction to obtain the intended product?
Determine the products of the reaction below.
Organometallic compounds, which are strong nucleophiles, can undergo reactions with epoxides. Draw the product of the following reaction, assuming that the C-Cu bond is ionic.
What are the correct structures of the intermediates in the following reaction scheme?
Draw the reaction intermediates and major products for the following reactions.Show the stereochemistry where applicable.
Is the reaction shown below expected to produce a mixture enriched in one stereoisomer or a racemic mixture? What are the stereoisomeric products in each case?
Give the product of the reaction below.
Determine the product of the addition reaction given below.
Provide a synthetic scheme, including the necessary catalysts, inorganic reagents, and carbon-containing compounds with no more than three carbons demonstrating the formation of 3-ethyl-2-methylhex-3-ene from hex-3-ene:
Propose a synthesis using the provided starting material, any inorganic reagents and catalysts, and any carbon-containing compounds with three carbons or less.
What organometallic compound does excess methylmagnesium chloride produce in the reaction with ZnCl2?
a) (CH3)2Zn
b) (CH3)2Mg
c) 2 MgCl2
d) ZnCl4
Determine the chloro-substituted compound that will react with (CH3CH2CH2)2CuLi to form the following product:
Provide the alkyl bromide that will react with (CH3CH2)2CuLi to form the following products.
Determine the product(s) that would result from the reaction of (2-methylbutyl)lithium with 7-hydroxyheptan-3-one.
The illustration below is a reaction in which a cuprate is the only organometallic that can produce the desired alcohol. Why can the same reaction not be carried out with a Grignard reagent or an organolithium?
Identify the halo-substituted compound/s that will react with (CH3CH2CH2)2CuLi to form the product shown below.
Provide the alkyl chloride that will react with (CH3CH2)2CuLi to form the following products.
Provide the alcohol formed in the reaction of (CH2=CHCH2)2CuLi with propylene oxide followed by acidic work-up.
Draw the product of the given reaction sequence.
Draw the structures of X and Y:
A compound with the formula C5H10Br2 reacts with NaOH to form an alcohol. The compound also reacts with Mg in ether to form a Grignard reagent. Reacting the Grignard reagent with dilute HCl results in isopentane. Provide possible structure(s) for the compound.
Identify the major product of the given reaction sequences.
Indicate the following compound can be prepared using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than three carbons.
The Reformatsky reaction can be used for the nucleophilic addition to the carbonyl of a ketone or an aldehyde. The reaction uses an organozinc reagent instead of a Grignard reagent. This organozinc reagent can be produced by the treatment of an α-bromo ester with zinc. The organozinc reagent is less reactive than a Grignard reagent therefore it can not be used for the nucleophilic addition to an ester.
Show how the given compound can be produced using a Reformatsky reaction.
Identify the missing species.
Identify the missing reagents.
Show how the following conversion can be accomplished using any necessary reagents, catalysts, and any other organic compounds with no more than two carbons.
Starting with bromocyclopentane, how could the following compound be prepared?
Provide a synthesis to produce the following compound using the given starting material.
Devise a synthetic pathway to produce the following compound using the given starting material.
Identify the missing products.
Provide necessary reagents to carry out the following reaction.
Provide necessary reagents to accomplish the following conversion.
Show how you would accomplish the transformation below. You can use any reagents you need to accomplish the synthesis.
What is the major product of the reaction shown below?
Synthesis of carboxylic acids from alkyl halides is accomplished by either converting the alkyl halide to a Grignard reagent followed by addition of carbon dioxide and then dilute aqueous solution of mineral acids, or by reacting the alkyl halide with cyanide ion, followed by subsequent hydrolysis of the resulting nitrile. Determine if either or both of these methods can be used in each of the following reactions, and explain why. Show the reactions you will use.
Determine which products can result from the following reactions involving organometallic reagents:
Can you identify what is wrong with the following Grignard synthesis?
Devise a synthetic route for the following conversion:
When an unknown compound, A, is treated with chromic acid, it gives a ketone, B. On the other hand, when the same compound A is treated with PBr3 in a separate reaction, C is formed which is further reacted with Mg in ether to form a Grignard reagent, D. When D and B are mixed, compound E is formed. Hydrolysis of E yields 3,4-diethylhexan-3-ol.
Give the structures of compounds A to E.
For the given synthesis, draw the structures of the missing products A through D.
As an introduction to multistep synthesis, devise the synthesis of 2-butanone from ethanol.
As an introduction to multistep synthesis, devise the synthesis of 2-methylbut-2-ene from propan-2-ol.
Devise an approach for the synthesis of 1-chloro-2-methylcyclohexane. You can start with cyclohexanone, any reagent that contains four carbon atoms or less, and any required reagent or solvent.
Devise a synthetic approach for the following molecule starting with no more than six carbon atoms.
Show how the following primary alcohol can be synthesized using formaldehyde as one of the reactants.
For the given synthesis, predict the missing products A through C. Assume that an excess of each reagent is used.
Determine the appropriate organocuprate reagent to accomplish each of these substitution reactions.
Determine the major product of these reactions.
Provide the alkyl halide that will react with diallylcuprate (CH2=CH–CH2)2CuLi to synthesize the compound below.
Propose a synthetic pathway for the compound given below starting with bromobenzene and any alkyl or alkenyl halide.a. but-2-en-1-ylbenzene
Propose a synthetic pathway for the compound given below starting with a bromoalkane and any alkyl or alkenyl halide.4-methylpent-1-ene
i) Name four reactions that can be done by Gilman reagents. ii) What do they have in common aside from the use of a Gilman reagent?
Show how you would synthesize the following compound by adding a Grignard reagent to an ester or a nitrile.
Grignard reagents react with carbonate esters in a similar fashion as with other esters.(i) Determine the identity of the major product of the reaction shown below.(ii) Show how to synthesize 2-methylpropan-2-ol from dimethyl carbonate and methyl bromide as the starting materials.
Which of the following sets of alkenes will produce the highest yield of a single product when subjected to olefin metathesis?
i) hex-1-ene and hept-1-ene
ii) hex-3-ene and oct-4-ene
iii) hex-3-ene and hept-1-ene