a) propose an outline of a possible mechanism for the conversion of a to b. provide illustrations as necessary. b) provide or suggest an explanation for the regioselectivity of "b" formation. Xlo CC13 CC14 Cl3C 2 eq. MeO- A CI CI
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- (i) The enolisation of ketone A can generate an equilibrium mixture of A and either enol B or enolate C. Give the structure of both B and C, and the mechanism for their formation from A under the given conditions. (ii) A HCI (cat.) NaOH (cat.) B с Draw the structure of the product obtained when A is dissolved in D3O*. Give a detailed mechanism to account for the structure you propose.The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent ofmCPBA forms A as the major product. A gives a molecular ion at 84 in itsmass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1HNMR spectrum of A is given below. What is the structure of A?Jut L Br HNO3/H₂SO4 NaOEt M N K (i) Give the structure of M and a mechanism for its formation. L and of bromoquinoline Explain the reactivity regioselectivity of the reaction. (ii) Give the structure of N and a mechanism for its formation. and bromoquinoline L Explain the reactivity of regioselectivity of the reaction.
- 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 H20(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)Answer ALL parts. (a) Provide reagents for the following transformation. No mechanism is required. NH2 (b) Suggest structures for A and B, and provide detailed mechanisms for their formation. 1. CI он NaOH (2eq) A ACONA/ACOH B 2. H3O* heat (c) Provide a detailed mechanism for the following transformation and suggest a chemical structure for C. All reagents are added together and no additional acid or base is needed. MENH2 COME C9H13NO2 lo (d) Suggest a retrosynthetic analysis for the following molecule, and outline a synthetic route, specifying reagents. No mechanisms are required. 3.
- SN1 substitution and E1 elimination frequently compete in the same reaction.(a) Propose a mechanism and predict the products for the solvolysis of2-bromo-2,3,3-trimethylbutane in methanola) Consider the reaction scheme below. -[•] PhLi HONH,, HCI A ELOH B D (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B.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.
- Answer ALL parts. (a) Treatment of enone C with tetrabutylammonium fluoride leads to the formation of heterocycle D. 2 steps BU4NF C9H1602 A + B D OSIME,tBu (i) Enone C can be prepared from alkyne A and aldehyde B in two steps via a gold-catalysed reaction. Identify A and B and provide reagents/conditions for a synthesis of C. (ii) Give the structure of D and classify the ring-closing reaction for its formation from C according to Baldwin's rules (iii) Sketch the key molecular orbitals involved in the ring-closing reaction in part (ii) and hence explain whether the reaction is favourable or unfavourable.(c) Propose a synthesis of C from D and any other reagents of your choice. Show reaction mechanisms and discuss regioselectivity. Ph N. S. Ph Ph .CO,Me NH2 C DSuggest a suitable mechanism for this multi-step reaction, and give products A and B