For each reaction below suggest structures for alkenes that give the indicated reaction products. There may be more than one answer in some cases

Provide the principle organic product(s) for the following reactions. If more than one product is expected, indicate the major product.  Indicate stereochemistry where appropriate.

f) Alkene X can be decomposed with hydrogen peroxide catalyzed by sodium tungstate to substance Q. This can be further degraded by iodoform reaction to substance R. Give the structures of substances Q and R. Xx S Na₂WO4 H₂O2 Q (C9H1603) 1: NaOH, 1₂ 2: H+ P₂O5 teplo - CHI3 R (C8H1404) P₂O5 teplo T g) The preparation of substance Q from substance X using hydrogen peroxide is a redox reaction. Identify the reductant and oxidant in this reaction, write the formal oxidation number to the atoms where it changes during the reaction and calculate the reaction. h) Substances Q and R undergo a reaction with phosphorous oxide under heating to form various products T and S. Determine the structure of substances T and S if you know their H NMR : 1H NMR (S): 2.2 (t, 2H); 1.8 (t, 2H); 1.3 (s, 6H). 1H NMR (T): 4.6 (d, 1H); 4.3 (d, 1H); 2.2 (t, 2H); 1.5 (t, 2H); 1.3 (s, 6H).

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11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).

(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from this alkyne. (I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration product. (b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown. Br2, H20 Compound X 100 - MS-IW-5644 80 60 40 - 20 - 20 40 60 80 100 120 140 160 180 200 220 m/z Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X: Br Br HO, IV V I II II Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the mass spectrum. 12 Relative Intensity

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G.223.