Pericycles: [3,3] sigmatropic rearrangement of [(2E)-but-2-en-1-yloxy]benzene 19 of 47 Part A Upon heating, the compound shown below undergoes a [3,3] sigmatropic rearrangement. Draw the reaction.
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- CH3 o alengoiga6 916w vtalmedoociote 6. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. () (a) Br Br Br (d) of (b) ОН ОН (o) Оама (c) (b). (d) Br C Br ОН (e) CI (e) CI CI CIA chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsHeating the following molecule in ethanol gave a major product with molecular formula C,H12 , which when treated with O3 followed by Me2S produced the diketone shown. Br CH3CH,OH 1. O3 C,H12 heat 2. Me,S (i) Deduce the structure of the product with molecular formula C,H12 from the information provided. Write an arrow formalism reaction mechanism to show how the compound with molecular formula C,H12 is formed. (ii) How would you perform the following transformation to obtain the final product as the MAJOR product. More than one step is needed. Show all the steps in your synthesis. Reaction mechanisms are not required. Br more than one step less than four steps OHC CHO
- What is the expected product for the following reaction?©GMU 2020 H2O cat. H2SO4 O The following compound: ОН Me O The following compound. OH Me + enantiomer The following compound: O The following compound: OH Me The following compound: + enantiomer11. Plan syntheses of the following compounds. You may use the given starting material and any compound containing five or fewer carbons. (a) MeO MeO CN TOXXON anything with five or fewer carbons. CN (b) (c)Isomenthone can be subjected to the following reaction conditions to generate a product with high regio- and stereochemical control. Provide the product of the reaction, including the stereochemistry at all relevant stereogenic centers. Draw a transition state structure that clearly indicates how this particular isomer is formed. Me 1. LDA (1.05 eq) -78 °C 2. i-PRCHO info. i-Pr C14H26O2
- + 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][18] Which of following compound will undergo solvolysis with methanol to yield the two shown? H3C OCH3 CH3 OCH3 (a) (15,3S)-1-bromo-1,3-dimethyl-cyclohexane (b) (1R,3R)-1-bromo-1,3-dimethyl-cyclohexane (c) (15,3R)-1-bromo-1,3-dimethyl-cyclohexane (A) (1R)-1-bromo-1,3-dimethyl-cyclohexane (e) (15)-1-bromo-1,3-dimethyl-cyclohexaneQ12. (1-bromoethyl)benzene 1 udergoes an elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance. CH; RDS Br C3Hg E1 2 3
- Elimination reactions of cis-and trans-1-bromo-2-methylcyclohexanes with NaOEt in E1OH can give the same or different main product, 1-methylcyclohexene (1) or 3-methylcyclohexene (2). Which of (a)-(d) indicates the main products? Br Br NaOEt NaOEt ELOH ELOH Me `Me Me Me cis 1 2 trans A. 1 both from the cis and trans substrate B. 2 both from the cis and trans substrates C. 1 from the cis and 2 from the trans substrate D. 2 from the cis and 1 from the trans substrateWhat product will be obtained for the below reaction: CH3 H3C-C=CH, + -? I-CI CH3 CH3 (A) H3C-C-CH2-Cl (В) H3C-C-CH2-I CI CH3 CH3 (C) H3C-C-CH3 (D) H;C-C-CH3 ClWhat product(s) would you expect to obtain from reaction of 1, 3-cyclohexadiene witheach of the following?(a) 1 mol Br2in CH2Cl2(b) O3followed by Zn(c) 1 mol HCl in ether(d) 1 mol DCl in ether(e) 3-Buten-2-one (H2C = CHCOCH3)(f) Excess OsO4, followed by NaHSO3