c) Scheme 1 shows the retrosynthetic analysis of compound M to the precursors via Functional Group Interconversion (FGI). State all the reagents (A-D) for the complete conversion.
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- (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)а) Consider the reaction scheme below. PhLi HONH,, HCI A ELOH B (i) Deduce the structures of compounds A, D and intermediate C. (ii) Outline the mechanism for the conversion of A to B. b) Pyrrole and indole both react with the reagents shown below to give compounds E and F respectively. Reagents: POC13, NazCO3, H2O N. E F (i) (ii) (iii) Show how the electrophile is generated. Account for the regioselectivity observed. Complete the mechanism for the formation of compound F.Provide all the missing products (A-C) and reagent (i). Suggest retrosynthetic analysis for this. B, NaOMe, MEOH CO(OMe)2 NaH COME OMe TSOH toluene
- Q4. Stabilized enolates and their surrogates. (a) Complete the following FOUR reaction schemes by drawing structures for the relevant stabilized enol, enolate or surrogate intermediates (A to D), and for the eventual organic products (E to H). (i) (ii) (iii) (iv) EtO CHO Me,SICI, Et N NaOEt EtOH HCO₂Et, NaOEt EtOH (i) t-BuNH, molecular sieves (ii) LDA A B C D MeBr, TICI 1. NaH 2. Mel 1. NaH 2. RBr 1. Me,SICI 2. RCHO, CsF E F G HPropose the structures of the intermediate compounds and the reagents needed to complete the following sequence of reactions. CI H₂SO4 (1)? (2)? HNO3 H₂SO4 AICI3 (3)? (4)? NO₂ KMnO4 (5)?4. Using arrows to show electron movements, write the stepwise mechanism for the formation of the main reaction product in the following reactions: (a) 1) CH₂MgBr, Et₂0 2) H3O+ HCI ? ? (b) O Br (Ph)3PCH₂CH₂Ph Li THF, -70 deg C to r.t. ? (c) O 1) LiAlH4, Et₂0 2) H3O+ 3) NaOH 4) CH₂ Br ?
- (d) Propose a reaction mechanism to account for the following reaction. AIC3(c) During Corey's synthesis of allomone he utilised the ketone shown below. OMe Outline the retrosynthesis to a monocyclic precursor.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 methanol
- Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis. O LO -O; H3O+ CH3NH/H₂SO4; NaOCH 3; (CH3)2NH/H2SO4; (CH3)2NH/H2SO4; CH3NH/H₂SO4; =O; H3O+ =O; H3O+ -O; H3O+ FO; H3O+8. Answer both parts A and B. A: Give mechanisms for all three reactions (a-c). H,1BO/HO- (a) HO, 18ö (b) H;C H3C OH + H®OCPH; (c) Ph Ph MEOH/MeO- -Ph -Ph + Me,0 Me-O Ph Ph When MeCO2Et is heated with acid in H2180 and the reaction is quenched before it is complete, both starting material and the ethanoic acid produced are labelled with 180. Explain. B:OH cis-J (iv) The allylic alcohol J can be synthesised as a single geometrical isomer from the appropriate aldehyde and an alkyne. Accordingly, provide a retrosynthesis and briefly explain the chemistry involved. (v) Design a method to synthesise the trans-alkene isomer of J and explain the chemistry involved.