1.70 An a,ß-unsaturated ketone reacts with a conjugated Wittig reagent to produce a relatively highly strained bicyclic compound. Draw the complete, detailed mechanism for this reaction. (A key intermediate has been provided.) H3C- `CH3 + (C6H5)3PO + H3C
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- 4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3Although a Wittig reagent can be prepared from 5-bromo-1,3-cyclopentadiene in the usual way, that Wittig reagent is unreactive toward ketones or aldehydes. Br 1. P(CGH5)3 R' ? No reaction 2. Bu –Li (a) Draw the complete mechanism showing the formation of the Wittig reagent. (b) Explain why that Wittig reagent does not undergo nucleophilic addition with ketones or aldehydes. O=UDraw the mechanism and predict the major product for each of the following reactions. (a) (b) O (c) NABH4 NABH4. 1. LIAIH4, Et,O ? CH;OH ? 2. H2SO4, H2O mOCH3 CH;OH
- (4d) and PhMgBr, followed by reaction with the acid. Please draw that mechanism here! Even though benzoic acid is reformed as the product, a reaction does take place between benzoic acid 1. PhMgBr HO, 2. H30*1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3Draw the complete, detailed mechanism (including curved arrows) for each of the following reactions occurring via (a) an E2 mechanism and (b) an E1 mechanism. If more than one possible product can be produced from the same type of mechanism, draw the complete mechanism that leads to each one. Pay attention to stereochemistry. (i) (ii) Br NaOH NaOH ? (iii) (iv) CI KOC(CH3)3 NaOCH3 H3C CH3 (v) CH3 (vi) CI CI КОН КОН ? 'CH3 "CH3
- Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions NOC XT :: [MgX]* H3C-C-0-CH3 CH₂CH₂CH3 :0: || H3C-C-CH₂CH₂CH3 + HạC—O: [MgX]* A ketone X2.) Show the complete mechanism and the major product formed from the reactions below. OMe CH,CH,OHQ7. Propose a detail mechanism for the following reaction. Use curved arrow to show the electron movement. H2SO4 он heat
- Draw a stepwise mechanism for the attached reaction that illustrateshow two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reactionconditions, even though it is a 1 ° alkyl halide.Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions X→UU :0: :O: || CH3-C-CH₂-C-OEt :OEt :O: || :0: || CH3-C—CH—C—0—OEt + EtO: HQ3. Please provide a curved arrow mechanism that can explain the reaction shown below. i) LDA ii) aq. workup Me Me TBSO CI Q4. a) Identify the main products of the following cycloaddition reactions. In each case, provide a curved arrow mechanism that accounts for their formation. Me OH H Me b) Provide a clear drawing that explains the stereochemistry of the product.