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- 7.) Which of the following is the product of CH,CHO + [Ag(NH3)2J* + OH- – product + Ag + H,0 + NH3 (1) CH,COO- (2) CH,CH,O (3) CH,COOA9 (4) CH;O-A tautometric keto (A) – enol(B) equilibrium may be formulated as follows (A) (B) CH3 – COH ß-----------àCH2 – CHOH Given the following bond energies: C – H = 435kJ mol-1 C – C = 368 C==C = 610 C – O = 357 kJmol-1 C==O = 748 kJmol-1 O – H = 462 kJ mol-1 Calculate the enthalpy change in going from Keto form (A) to the enol form (B)(b) Complete the following reactions : (i) D H3C CH3 H H كما .NO2 B | Bra/Dioxane .COCH3 A
- 4. Protonation of alcohol A and subsequent loss of water, produces the intermediate B. CH3 CH; CH, CH, — с — сH, CH, CH;CH, - C- CH, CH; | OH A B (a) (i) Name alcohol A. (11) What type of species is intermediate B? (iii) Draw the structures of the two alkenes which can be formed from species B by removal of a proton. Label as C the alkene which shows geometrical isomerism. (b) The intermediate B is readily attacked by nucleophiles such as water. What is the essential feature of a nucleophile? (c) State what final colour you would see if alcohol A were warmed with acidified potassium dichromate(VI). Explain your answer. Colour Explanation . (ii) Draw two structural isomers of alcohol A which form branched chain ketones when heated with acidified potassium dichromate(VI), but which could not form alkene C on dehydration.Predict the major product of the following reaction. (CH3)3C-OOH LOH TI[OCH(CH3)214 (-)-DET Dom -OH 11 OH Io ||| Ø OH IVOH - NH, Br2/KOH →product; 1. (a-hydroxy amide) Product of this Hoffmann bromamide reaction is : OH (a) Ph – Ĉ-CH3 (Ъ) Ph — CHO (c) Ph- CH3 (d) Ph – CH2 -NH2 NO2
- Identify (A) in the following reaction. 2H2 Pt (A) KMNO4 Warm conc. || С — С — о—н |CO,H + HO CO2H cis-cyclo hexane 1,2-dicarboxylic acid (a) (b) (c) (d)Which best represents the major organic product(s) of the reaction shown? (A) (C) O O A O 'Br OH + OH OH (B) (D) xs. HBr OH Br + Br BrProvide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. (a) OH HIO4 (the protecting group is remained) CHO H HOH2C OH (b) CHO -ОН NaCN # HO -H H -OH CH₂OH (c) CHO HO- -H HO -H NH₂OH 張一 H -OH H -OH CH₂OH i) Ba(OH)2 ii) MeOH, H₂SO4 NaOAc Ac₂0 NaOMe MeOH
- Predict the product(s) for the following reaction. O ll + enantiomer I OI ||| OH O IV OH CN OH + enantiomer || 1. NaCN 2. H₂O CN "ОН + enantiomer ||| IV CN CNPredict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HASHC CH CH3CO2H H,SO, H3C-C-O-C=CH2 H HgSO, Acetylene Acetic Acid Vinyl acetate Acetylene reacts with acetic acid in the presence of H,SO4 and HgSO4 to yield vinyl acetate, a monomer used in the production of poly(vinyl acetate). The reaction mechanism includes the following steps: 1. Formation of a bridged mercurinium ion intermediate between Hg- and acetylene; 2. Addition of acetic acid to open the three-membered ring; 3. Proton transfer to solvent to give an organomercury vinyl ester3; 4. Addition of H to the alkene to form a carbocation; 2+ 5. Expulsion of Hg²+ to form the alkene. Diagram the mechanism on a separate sheet of paper, and then draw the structure of the product(s) of step 3. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Draw organic species only. • Do not include counter-ions, e.g., Na, I, in your answer.