, we suggested that the mechanism of Fischer esterification of carboxylic acids is a model for the reactions of functional derivatives of carboxylic acids. . Suggest a One of these reactions is that of an acid chloride with water mechanism for this reaction. R-C-CI + H,O R-Ĉ-OH + HCI
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Q: b)
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A: The solution is given below -
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- When pyrrole is added to a dilute solution of D2SO4 in D2O, 2-deuteriopyrrole is formed. Propose a mecha-nism to account for the formation of this compound.Outline the synthesis of racemic 3-methyl-3-heptanol, Et(Me)C(*)OHn-Bu, starting from alcohols of four carbons or fewer and any inorganic reagents or solvent needed.Give a rearrangement reaction equation to synthesize N-ethyl-2-methyl-buthylamide from the corresponding α-diazoketone. Give the structures of all intermediary products. Do not give a mechanism.
- (a) Write a suitable chemical equation to complete each of the following transformations :(i) Butan-l-ol to butanoic acid(it) 4-Methylacetophenone to benzene-1, 4-dicarboxylic acid(b) An organic compound with molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollen’sreagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzenedicarboxylic acid. Identify the compound.Please write out the mechanism for the acid (WHICH IS 3-BROMOBENZOIC ACID) reacting with anilide. PROVIDE THE MECHANISM AND BRIEFLY EXPLAIN THE STEPS OCCURING PLEASEWhen heated, carboxylic salts in which there is a good leaving group on the carbon beta to the carboxylate group undergo decarboxylation/elimination to give an alkene.Propose a mechanism for this type of decarboxylation/elimination. Compare the mechanism of the decarboxylations with the mechanism for decarboxylation of b-ketoacids. In what way(s) are the mechanisms similar?
- The following scheme shows the retrosynthetic analysis of 1-isopentylaziridine to form series of intermediates via Functional Group Inversion (FGI). Choose the correct reagents of N-S for the respective conversionOutline a synthesis of the following compounds (A-C) from acetoacetic ester OR malonic ester. Show the starting material and reagents. If the synthesis is not possible, indicate why. A) hept-6-en-2-one B) 2-benzylheptanoic acid C) 3-isobutyl-2-heptanoneCompelling evidence for the existence of a tetrahedral intermediate innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.
- What is the name of the mechanism where camphor is reduced to isoborneol? Is it Nucleophillic/Electrophilic Addition/Substitution? Give explanation also.The reaction of sodium borohydride with ketones proceeds rapidly at room temperature, forming an intermediate borate ester which is hydrolyzed to give the product alcohol: 4 R2C=O + Na+BH4- ---> (R2CHO)4B-Na+ (R2CHO)4B-Na+ + 2H2O ---> 4R2CHOH + Na+BO2- Rewrite these two steps using benzil as the ketone, and using structural formulas throughout, rather than the condensed forms above.Compound A has the molecular formula C14H25Br and was obtained by thereaction of sodium acetylide with 1,12-dibromododecane. On treatment ofcompound A with sodium amide, compound B (C14H24) was obtained. Ozonolysisof compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation ofcompound B over Lindlar palladium gave compound C (C14H26), andhydrogenation over platinum gave compound D (C14H28). Further, C yieldedO=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through Dso as to be consistent with the observed transformations.