Draw the HOMO of the following 5-carbon conjugated pi systems and draw the thermal and photochemical electrocyclic ring closure reaction for each one. Determine whether each ring closure mechanism involves either a conrotatory or a disrotatory motion. 1. H2C=CH-CH=CH-CH,(+) 2. H2C=CH-CH=CH-CH,-)
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- Draw the organic product(s) of the following reaction, including counter-ions. NaOC2H5 / C2H5OH CH3CH2-CEC-H • You do not have to consider stereochemistry. • Include cationic counter-ions, e.g., Na* in your answer, but draw them in their own sketcher. Separate multiple products using the + sign from the drop-down menu. • If no reaction occurs, draw the organic starting material. n [F ?Rank the following groups in order of priority from highest (1) to lowest (3). < < -COO- -CH3 -NHCH3Arrange the substituents in order of decreasing priority when determining E/Z stereochemistry of an alkene (i.e., 1 is the highest priority substituent, 4 is the lowest priority substituent). – NHCH3 II - CH v - OCH3 -CH,CI >
- Draw the structures of A - D from the following electrocyclic and cycloaddition reactions. hv CH3 heat B A D CH35. Which bromocyclohexane starting material would react faster - the cis or trans, and explain why? Draw both chair forms of the starting material to prove your point. Br K* OC(CH) K* OC(CH); Br cis trans11. Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3- methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product. (
- 5.) Given the following three reactions of enantiomerically pure starting materials, please identify products A and B for each line (given the product molecular formulae), using dashes and wedges where appropriate, the meso (optically inactive) product and the chiral (optically active product). NaBH4 CH3OH A CHo02 + B CSH1002 optically active HO optically inactive (R)-3-hydroxycyclopentanone OH Os04 (cat) (CH3)3COOH C CH1203 optically inactive + D CH1203 (2R, 3E)-2-hydroxy-3-pentene optically active OH Os04 (cat) (CH3)3COOH E CsH203 + F CSH1203 optically active optically inactive (2R, 3Z)-2-hydrox y-3-pentenePlease fill in the missing reactants, reagents or products in the following reactions. Indicate relative stereochemistry where it is necessary CI j)Starting from the wedge-and-dash structure below (sighting down the indicated bond), rotate the back carbon to provide the structure in the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. H H|||| Br H₂C Br H CH₂ Edit Newman Projection CH3 CH3
- Provide an appropriate name for the following compound. 3-fluro u-methyl 5-chloro 7 OH CI F 5-chbro-3 fluro-4 methyl non-2-enol 2) Draw the molecule that corresponds to (3R,5R,6R)-5-cyclopropyl-6-ethyl-3-iodo-1-methylcyclohex-1-ene.a) H₂ Pd C-C -H and -H + A-B For the following reagents, indicate the following: a) what is added accross the double bond; b) is the addition stereoselective/stereospecific? If yes, do A and B add syn or anti?; c) draw the product, with relevant stereochemistry, when the reagent system shown is reacted with 1-methylcyclopentene. The answer to the first reagent system is shown below. (i) b) yes, syn addition | | -C-C- (achiral, stereochem. not observable) | I A B (ii) a) 1) 9-BBN 2) H₂O2, NaOH(aq) b)Draw the product of each thermal electrocyclic ring closure. CH3 b. CH3O2C CO,CH3 a. CH2 (2E,4Z,6Z)-2,4,6-0ctatriene