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 -NHCH3Addition of HCl to alkene X forms two alkyl halides Y and Z. Explain why addition of HCl occurs at the indicated C=C (called anexocyclic double bond), rather than the other C=C (called anendocyclic double bond).
- 5. 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. (Draw the structures of A - D from the following electrocyclic and cycloaddition reactions. hv CH3 heat B A D CH3
- Please fill in the missing reactants, reagents or products in the following reactions. Indicate relative stereochemistry where it is necessary CI j)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-penteneStarting 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)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. # O H3C H Drawing > CI ||||| H Atoms, Bonds and Rings Tap a node to see s