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.
Fill in the missing reagents to complete the synthesis.
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.
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.
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+
For the synthesis below, start with chlorocyclopentane and predict the structures of products 1 through 5.
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: