Compound A (CH12: reacts with 1 molar equivalent of H₂ over a Pd catalyst) gives the product(s) below on oxidative cleavage with KMnO, in acidic solution. Propose a structure for A Compound A CH₂CH₂CO₂H + a ketone
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- The treatment of (CH3)2C = CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its H NMR and IR spectra.A key step in the synthesis of a natural product is shown below. Answer sections (iv) and (v) related to this reaction. OH R CO₂Me + S S P CO₂Me Heat H H CO₂Me (iv) Give a curly arrow reaction mechanism for the formation of compound Q and suggest why the formation of the given diastereomer is favoured. (v) Compound P can be formed from S and R. Suggest the identity of S and state what type of reaction can be used to form P.Compound 1 has been shown to be a useful precursor in the synthesis of natural products. (Org. Lett. 2004, 6, 4439-4442). In principle, four stereoisomers are possible when this compound is subjected to catalytic hydrogenation. Draw these stereoisomers and describe their relationships. HO O OH H₂ - ? Pt Modify the four structures below, as necessary, to draw the four stereoisomers that are possible from catalytic hydrogenation of compound 1. Use the single bond tool to interconvert between double and single bonds.
- -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the E alkene, and the other gives the Z alkene. Which diastereomer gives which alkene? Account for the stereoselectivity of each -elimination.Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.
- 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).A key step in the synthesis of a natural product is shown below. Answer sections (iv) and (v) related to this reaction. OH R CO₂Me S ان - شبه P CO₂Me Heat H H CO₂Me (iv) Give a curly arrow reaction mechanism for the formation of compound Q and suggest why the formation of the given diastereomer is favoured. (v) Compound P can be formed from S and R. Suggest the identity of S and state what type of reaction can be used form P.asap
- Q3] Diethyl malonate was treated with 2 moles of NaH followed by reaction with 1,4-dibromo-2-butene providing compound (A). Hydrolysis of compound A under heat 200 °C affording compound B; which was treated with PBr3 then with methanol/H+ affording C. The compound C then was exposed to ozonolysis conditions providing D. Finally two moles of ammonia react with D providing E. What are structures A..to .E?? A B C D E(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below. Propose a structural formula for this compound. 1. PhMgBr (2 eq.) 2. H'/H>O C18H2202 bj 1o 14 10I f6 40 & 3 4 00 (8)(10pts) Compound A, C10H16, was found to be optically active. On catalytic reduction over a palladium catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, CioH2o. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid (CHCOOH). The other fragment, compound C, was an optically active carboxylic acid, C8H14O2. Write reactions, and draw the correct structures for A-C, explain your answer in detail.