3. Cyclooctadienyllithium provides an example where electrocyclization of a pentadienyl fragment occurs. (a) Using frontier molecular orbitals, determine whether the cyclization would proceed conrotatory or disrotatory (4 pts). H heat H
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- 3. (a) The 3C-NMR spectrum of one of the three xylenes (dimethyl benzenes) show resonance at 8 = 10 1, 126-2, 130-0 and 138-8 ppm (proton deccupled). ident:fv the structure of the xylene and ass:gn %3D the &-values.a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?(a) Complete the following sequence of reactions (i.e., give the structure for compounds A and B), giving structural details of all key intermediates. heat & A COOCH3 H₁₂ Ni (b) Provide the bond line structures for the pair of compounds used for the Diels-Alder synthesis of the compound shown below. O B COOCH3 (c) Draw the two major products obtained when (3E,5Z)-2,2,3,6,7-pentamethylocta-3,5-diene reacts with HBr at low and high temperatures. Label the products as the kinetic or thermodynamic product AND, if applicable, use dashes and wedges to show the correct stereochemistry in the obtained products.
- PQ-21. From the standpoint of reactivity, which is the poorest dienophile to react with 2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction? H (A) CO2CH3 (B) (C) (D) CNPlease help with 4c, 4d, and 4e. We havent learned kaw of equivalents so please do 4c a different way. thank youCyclopentadiene is unusually acidic for a hydrocarbon. Which of the following explains why that is? The carbon atoms of cyclopentadiene are all sp hybridized. A В Cyclopentadiene is aromatic. Removal of a proton from cyclopentadiene yields an C aromatic anion. Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. D Removal of a hydride ion from cyclopentadiene produces an E aromatic cation. H H. cyclopentadiene
- Irradiation of diene A at 254 nm affords a photostationary mixture of A with triene B. Provide a mechanism for the formation of B and define the stereochemistry of the alkenes, explaining this stereochemical outcome by reference to the interacting frontier molecular orbitals. H. hv H B7В. (2 Draw the structure of the product, substrate or condition in the following reactions (should clearly indicate the stereochemistry). (а) OH (b) OsO vaHSO3 (c) 1) (sia)2 BH 2) NaOH/H,O2 H20 (d) HBr (2 equiv) Br, Br Hint: This is the only product formed (e) Br Br2 H20 OH (f)2 Write the IUPAC name for each compound. Ο COC-M (a) HV Ο 0 || (d) H₂N- C (b) CH₂(CH₂),COCH, OTT HO noitos2) alodo d diw sobirbydaA to noilo ono evig of alcools dikw 39891 abitbydA (8.81 (c) CH₂(CH₂)4CNHCH, no bae totes me to slom 0 O CNH₂ با нио но но но HOOH + HOOO HO HOOOH OHO.HOOD HO || (e) CH₂CO-A iw sobixbydnA to noltoso. driw do A (D681 moitoo@) aoniMA "I w bn shomme a onions to solomeowths of elom ono bas shima Joubo aviy oj vig OH OHO bertiup bios biydisororesidenten (f) CH3CHCH₂COCH₂CH3
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.Chemistry 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (а) NaOEt heat (b) heat (c) Br NaCN DMF (d) (e) OH H,SO,/H,PO, heat (f) HBr (g) 1) BH. THE 2) H,0, OH (h) 1) Hg(OAC), H-0 2) NaBH, (i) KMNO, NaOH ColdIllustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.