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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ORGANIC CHEMISTRY
- (c) Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is combined with methanol in the presence of catalytic acid.arrow_forwarda) What is the major alkene formed when A is dehydrated with H2SO4? (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(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) Label the carbon–carbon double bond in A as E or Z. (b) Draw the products (including stereoisomers) formed when A is treated with H2O in the presence of H2SO4.arrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. Part (b), then CH3COCl, AlCl3arrow_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_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_forwardDraw the product(s) formed when A is treated with each reagent. (a) NaBH4, CH3OH (b) [1] LiAlH4; [2] H2O (c) CH3CH2MgBr; [2] H2Oarrow_forward
- For alkenes A, B, C, and D: (a) Rank A—D in order of increasing heat ofhydrogenation; (b) rank A—D in order of increasing rate of reaction withH2, Pd-C; (c) draw the products formed when each alkene is treated withozone, followed by Zn, H2O.arrow_forwardIdentify the lettered compounds in each reaction sequence.Draw the product formed when phenylacetonitrile (C6H5CH2CN) istreated with below reagent. [1] DIBAL-H; [2] H2Oarrow_forwardDraw a stepwise mechanism for the following reaction, which was used in the synthesis of ezetimibe (Section 20.6), a drug used to treat patients with high cholesterol.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning