Concept explainers
(a)
Interpretation: The structure of C, which is formed by oxy-cope rearrangement of B with
Concept introduction: Cope rearrangement is a thermal
Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
(b)
Interpretation: The mechanism for the conversion of C to the bicyclic alcohol D is to be drawn.
Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
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PKG ORGANIC CHEMISTRY
- 5) Draw the enols available to compounds A-D. Explain why A is 100% enolized but B, C, and D are 100% ketone. B Darrow_forward(c) Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is combined with methanol in the presence of catalytic acid.arrow_forward(a) Draw a stepwise mechanism for the conversion of A to B. (b) What product would be formed if C was exposed to similar reaction conditions?arrow_forward
- Draw a stepwise mechanism for the reduction of epoxide A to alcohol B using LiAlH4. What product would be formed if LiAlD4 were used as reagent? Indicate the stereochemistry of all stereogenic centers in the product using wedges and dashed wedges.arrow_forward(a) Draw two different halo ketones that can form A by an intramolecular alkylation reaction. (b) How can A be synthesized by an acetoacetic ester synthesis? of Aarrow_forward(a) Draw a stepwise mechanism for the reaction of ethyl hexa-2,4-dienoate with diethyl oxalate in the presence of base. (b) How does your mechanism explain why a new carbon–carbon bond forms on C6? (c) Why is this reaction an example of a crossed Claisen reaction?arrow_forward
- Consider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?arrow_forwardDraw a stepwise mechanism for the conversion of lactone A to ester Busing HCl in ethanol. B is converted in one step to ethyl chrysanthemate,a useful intermediate in the synthesis of a variety of pyrethrins, naturally occurring insecticides with three-membered rings that are isolated fromchrysanthemumsarrow_forward(a) What is the major alkene formed when A is dehydrated with HS2O4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forward
- Draw a stepwise mechanism for the attached reaction that forms ether D. D can be converted to the antidepressant fluoxetine (trade name Prozac) in a single steparrow_forwardDraw the product(s) formed when A is treated with each reagent. (a) NaBH4, CH3OH (b) [1] LiAlH4; [2] H2O (c) CH3CH2MgBr; [2] H2Oarrow_forwardIdentify the lettered compounds in each reaction sequence.Draw the product formed when phenylacetonitrile (C6H5CH2CN) istreated with below reagent. [1] DIBAL-H; [2] H2Oarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning