2. (2 E) Prof. Amos Smith has built a career utilizing dithianes (Acc. Chem. Res. 2004, 6, 365-377) and their umpolung capabilities. An early example is the synthesis of bertyadionol, and abbreviated structures for one of the steps in the synthesis are shown below. Draw the compound which is the crucial umpolung intermediate, and label the positions acting as a donor and acceptor which are utilized in the reaction below. R 1. BuLi 2. O S НО. S R
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- 7B. (2 reactions (should clearly indicate the stereochemistry). Draw the structure of the product, substrate or condition in the following (a) ОН (b) Ме 1) OsO4 2) NaHSO3 (c) 1) (sia)2BH 2) NaOH/H2O2 H20Q4. Nucleophilic attack at carbonyl with loss of carbonyl oxygen. For this question, answer AT LEAST FIVE of the SIX parts. (a) For the FOUR reactions listed below, draw structures of the major organic products. (i) (ii) (iii) HO OH ●... NMe₂NH₂ cat. dry HCI H Ph₂pⓇ THFG. (a) Identify the acid and base in each of the following reaction. (b) Show the mechanism by using arrows. (c) For each reaction, what acid-base concept (or definition) is applicable in classifying them? Explain why. 1. :ö: CH3C-H + CH3O: :0: CHIC-H :OCH3 2. :0: :0: CH3-C-CH3 + H H. H. CH3-C-CH3
- Synthesize the following compound from benzonitrile (C6H5CN):? Please don't provide hand written solution....Q4. Stabilized enolates and their surrogates. (a) Complete the following FOUR reaction schemes by drawing structures for the relevant stabilized enol, enolate or surrogate intermediates (A to D), and for the eventual organic products (E to H). (i) (ii) (iii) (iv) EtO CHO Me,SICI, Et N NaOEt EtOH HCO₂Et, NaOEt EtOH (i) t-BuNH, molecular sieves (ii) LDA A B C D MeBr, TICI 1. NaH 2. Mel 1. NaH 2. RBr 1. Me,SICI 2. RCHO, CsF E F G H(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.
- (b) acid, HNO3 to produce compound L. The reaction of compound L with bromine, Br2 in the presence of iron tribromide, FeBr3 produced compound M. Benzene also undergoes Fridel-crafts alkylation reaction with chloroethane, CH;CH2CI using catalyst N to produce compound P. Benzene, CeHe undergoes substitution reaction with concentrated nitric Benzena, CsHe menjalani tindak balas penukargantian dengan asid nitrik, HNO, pekat untuk menghasilkan sebatian L. Tindak balas sebatian L dengan bromin, Brz dengan kehadiran ferum tribromida, FeBrs menghasilkan sebatian M. Benzena juga menjalani tindak balas alkilasi Fridel-crafts dengan kloroetana, CH3CH2CI dengan menggunakan pemangkin N untuk menghasilkan sebatian P. (i) Draw the structural formula of L, M and P. Lukiskan formula struktur bagi sebatian L, M dan P. (ii) State catalyst N. Nyatakan pemangkin N. (iii) Show the formation of electrophile that will be reacted with benzene for the formation of compound P.Q6. Enolates and their surrogates. (a) Rank the acidity of the following compounds from LEAST (left) to MOST (right) by entering the corresponding numbers in the boxes provided. 1 4 2 NaNH, CO₂Me 5 3 CHO (b) Complete the following reaction products by adding the correct bonds, atoms and charges, as necessary.1. a) Consider the reaction scheme below. PhLi HONH,, HCI A ELOH D (i) Deduce the structures of compounds A, D and intermediate C.
- In each of the following electrophilic substitution reactions (i) as a first step show the“preactivation” or generation of an electrophilic species; (ii) using arrows provide a mechanisticexplanation of the course of the reaction (show all resonance structures contributing for intermediatearenium ion stabilization); (iii) write all major products of the reaction. Friedel-Crafts acylation of anisole with 2-methylpropanoyl chloride ((CH3)2-CH-COCl) inthe presence of AlCl3 as a catalyst.(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -(d) Answer both sections () and (i). O Arrange the following compounds in order of increasing boling point, and briefly explain ye answers: CH.(CH.).CO,H CH(CH;)»CHO CH(CH;)»CH.OH. Page 2 of 5 Question 2 is on the next page.. (4) Arrange the following compounds A - C in order of increasing basicity, and explain the reasons for your choice of order. NH B