Considering which of the OH groups should be more accessible to MsCl, suggest a mechanism for the rearrangement of the cyclobutane to the cyclopentane. Me Me Me Me Et3N, MSCI OH -30 to 4 °C OH Me Me
Q: Question 25 Predict the FINAL (?) product (or a mixture of products) for the following synthetic…
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- Qa 18. Bromination of 5a-cholestan-3-one occurs at C-2 or C-4 to give 2 regioisomers. Two unsaturated ketones with lambdamax = 230 nm and lambdamax = 241 nm are yielded during dehydrobromination. Use Woodward-Fieser rules to distinguish between the two.Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.+ H3C- CH₂ - CH2 - COR and have undergone McLafferty rearrangement and Ortho effect respectively. What are the possible fragments obtained as a result of these processes ? COOCH3 OH + (A) [R-CH₂-C (A) R-CH₂-CH₂ - CH₂ - COH @E OH]: [c C6H4 O and CO (B) H₂C=CROH and H₂C = CH₂ [2] : [ C₂H4O3 and CH4 (C) (D) H₂CCROH and C₂H4; [(C6H4O), CO and CH₂OH] RH, C₂H4 and CH₂CO; [(C₂H4O), CO and CH₂OH]
- Chemistry sagarB) Please draw the mechanism of formation for ONE of the functional groups. excess C6H₂O₂ IR = 1720 cm-1 ¹H-NMR 2.65 (s. 8H) HO _OH H* catalyst C10H1604 ¹H-NMR 3.8 (s, 8H) 1.75 (s, 8H)Myo-inositol, the most prominent naturally occurring form of inositols, is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells. It is generated in vivo from the aldol cyclization of glucose-6-phosphate to myo-inositol-1-phosphate
- N-Nitrosamines by themselves are not significant carcinogens. However, they are activated in the liver by a class of iron-containing enzymes (members of the cytochrome P-450 family). Activation involves the oxidation of a C-H bond next to the amine nitrogen to a C-OH group. OH ОН N=0 N=O Og 'N- H+ H N,+ cyt P-450 N-Nitroso- 2-Нydroxy-N- nitrosopiperidine An alkyl diazonium ion piperidine (a carcinogen) Show how this hydroxylation product can be transformed into an alkyl diazonium ion, an active alkylating agent and therefore a carcinogen, in the presence of an acid catalyst.5:42 PM Wed Jan 26 @ 69% + : 28) Provide the structure of the major organic product in the following reaction. Show any stereochemistry. CH30, CH3 29) Is the cycloaddition reaction between the allyl anion and ethylene thermally allowed? To answer, draw the HOMO of the allyl anion and the LUMO of ethylene, and comment on the symmetry match between them. 30) UV spectroscopy measures the energy required to promote an electron from the molecular orbital. 30) molecular orbital to the A) lowest occupied, lowest unoccupied B) highest occupied, highest unoccupiedPropose a mechanism
- The dragmacidin class of natural products has been isolated from various marine sponges. They have been shown to have many interesting biological properties, including anti-viral, anti-fungal, and anti-bacterial activity. (+)- Dragmacidin D, shown below, was also made in the laboratory, which allowed the structure to be confirmed (Org. Lett. 2015, 17, 1529-1532). Part 1 ΗΘΗ H-N N-H * (-6) R (+)-Dragmacidin D R = "N-H The positive charge in dragmacidin D is delocalized. Draw all resonance structures that show delocalization of this charge, by modifying the given structures as needed. Include the original structure as one of the possible resonance forms, and include relevant formal charges in your structures. Do not add any resonance arrows or curved arrows. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds. Br -H1) In the following reactions, give the nature and possibly the stereochemistry of A1, A2 and B and justify the proportions obtained. 4 1=3 |=1 CI ull OH KOtBu 3 DMSO H₂SO4 majority A1 A1 + 2)When the first compound is treated with MeONa in methanol, compounds A1 and B are also obtained, as well as a higher molecular weight compound C, which has a higher molecular weight. B are also obtained as well as a higher molecular weight compound C whose 1H NMR spectrum is given below. Justify the formation of C. 2 PPM equimolar mixture + isomere of A1 1=3 mobilie B A2 1=3 1=3 1 1=3 OQ51 Give the major product of the following reaction CI NaOCH3 ?
