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- (iii) Rank the carbonyl compounds given below in terms of their relative reactivity with sodium borohydride. RT R CH3 CI (iv) Suggest two factors which combine to make the aldehyde react with sodium borohydride at a different rate from the ketone. (v) Based on electronegativity one might assume that the ester and acid chloride possess similar reactivity towards nucleophiles. Suggest why this turns out not to be the case (your answer should mention resonance and inductive effects).nswer all parts of this question. 3 CH3I NaOH solution NH2 [7] (11) (i) AGOH (replaces I with "OH) (ii) 180 °C [8] (14) (12) (13) 95% 5% Provide a detailed mechanism to account for the formation of the product (11) in reaction [7]. You may omit the reaction with the third equivalent methyl iodide (as it is a repeat).10) Provide the missing products. (CH3)3CCH₂C1, AIC13 KM₂04, 820, NaOH 2) acid work up
- Draw structures to correspond with the following common and systematic names: (e) N,N-dimethylformamide (f) benzoic propionic anhydride2. (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. S. S R 1. BuLi 2. O HO S Sdo ii and iv with explanation
- 7. Answer ALL parts of this question. (a) Answer BOTH parts of this question Reaction of the carboxylic acid below (Scheme Q7(a)) with bromine in the presence of dibenzoylperoxide gives rise to an unstable compound A (CSH&BR2O2) that gives a stable compound B on treatment with a base. The stable compound has IR peaks at 1735 and 1645 cm and NMR peaks at &H (ppm) 6.18 (1H, s), 5.00 (2H, s) and 4.18 (2H, s). Br. Base (PhCO, Scheme Q7(a) (1) What is the structure of the unstable compound A? (i) Show the mechanisms for the two steps in the reaction (b) Answer BOTH parts of this question Tetraphenylporhyrin (TPP) is a singlet sensitiser that reacts with oxygen and can engage in pericyclic reactions (Scheme Q7(b). OH O. TPP hv Scheme Q7(b) (i) Explain the difference between a singlet and a triplet state. (ii) Show the mechanism for the reaction shown in Scheme 07(b) (ii) Consider the below reaction (figure Q7(c)), Show the structure of the product (C) anc the mechanism Scheme Q7 (b)A student was given from the list of the conmpounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test? A = haloform B = Brady A = haloform D = Brady B = haloform A = Brady B = haloform D = Brady D = haloform A = Brady D = haloform B = BradyQ8:- Arrange the compounds of each set in order of basicity:? Explain your choice ? Aniline , p-methoxyaniline, p-nitroaniline Q9: Outline all steps in a possible laboratory synthesis of each of the following compounds from benzene and toluene and any needed aliphatic and inorganic reagents. (a) p-iodobenzoic acid (b) 2-amino-4-methylphenol Q10:- How can prepare Phenol by Industrial and lab methods ? Compere between them ?