Concept explainers
Interpretation:
When previtamin D2 (which is identical to previtamin D3, p. 1478, except for the R-group) is isolated and irradiated, ergosterol is obtained along with a stereoisomer, lumisterol. The origin of lumisterol is to be explained mechanistically.
Concept introduction:
Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. In phase orbital overlap results in symmetry allowed electrocyclic reactions. Selection rules of electrocyclic reactions are;
No. of electrons | Activation mode | Stereochemistry of rotation |
4n | Thermal Photochemical |
Con Dis |
4n + 2 | Thermal Photochemical |
Dis Con |
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Organic Chemistry
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- How would we know using aromatic vicinal coupling that the c-c bond was formed between compound B and C to for the product A? (HO)₂B. Br ------ compound A compound B compound Carrow_forward(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_forwardPractice Problem 19.54 Z Your answer is partially correct. Try again. Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c): NH2 HO Eto OEt A: B: C: D: E: F: OH OH но CN G: H: I: J: (a) [H*], excess EtOH, (-H20) Major Product(s): (ь) NaBH4, Meон B Major Product(s): (c) LAH followed by H20 Major Product(s): SHOW HINTarrow_forward
- Rhodamine B is useful dye prepared in a manner very similar to fluorescein. Due to the nitrogen donating groups, rhodamine B absorbs 550 nm light and fluoresces 580 nm light. a) What color would you expect for a rhodamine B solution? b) What is the color of the fluoresced (emitted light)?arrow_forwardThe saccharide shown here is present in some plant-derived foods. (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s). (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not? (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not? (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not? (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.arrow_forward(a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 26, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer’s disease.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning