Given the reversibility of the acid-catalyzed DAGUI er! obivo17 hydrolysis/Fischer esterification shown, how would you modify the reaction to make (a) a carboxylic acid or (b) an ester? o 133 (014049 + H₂0 = -0X0 362790-9 O OH on Wag + HOVIC Forlo 3007032015/
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- Which of A to E shows the likely product obtained from LiAlH4 reduction of the ketoamide shown below?When 4-dimethylaminopyridine (DMAP) is added in catalytic amounts to acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetylpyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetylpyridinium intermediate.Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.
- Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OHProvide the mechansim using curved arrows of the reaction of p-t-butyl phenol treated with acetic anhydride in AlCl3. Include resonance stabilized intermediates and if more than one product is formed, label them as major, minor, etc. thank you for the help
- what is the major E1 product for the structure?select the most appropriate reagent(s) to effect the change. K2Cr2O7, H+ H2, Pd 1. Disiamylborane, 2. HO–, H2O, H2O2 NaOCl H2SO4, HgSO4Predict the products formed when limonene reacts with the followingreagents.(a) excess HBr (b) excess HBr, peroxides (c) excess Br2 in CCl4(d) ozone, followed by dimethyl sulfide (e) warm, concentrated KMnO4 (f) BH3 # THF, followed bybasic H2O2
- (2R, 3S) -3-phenylbutan-2-ol tosylate undergoes E2 removal when treated with sodium ethoxide.Draw the structures of the products obtained (one majority and one minority). Use Newman's projections for this reactive in this deduction.Qa 18. Bromination of 5a-cholestan-3-one occurs at C-2 or C-4 to give 2 regioisomers. Two unsaturated ketones with lambdamax = 230 nm and lambdamax = 241 nm are yielded during dehydrobromination. Use Woodward-Fieser rules to distinguish between the two.Draw a mechanism of the reduction of 188Re-perrhenate (Re(VII)) to Re(V) by using SnCl2.