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Compound 1 is a halogenoalkane. It undergoes a reaction at room temperature with sodiummethoxide (NaOCH3) in methanol to form compound 2. The rate of reaction is determinedexperimentally to follow second-order

kinetics. a. (4 marks) Sketch a reaction coordinate diagram for a second order reaction and labelthe diagram with reactants, products, transition state(s) or intermediate species (if any). b. (4 marks) What is the stereochemical designation (R or S) of 1 and 2. Show yourworking. c. (3 marks) On the basis of the information of the reactants and the reaction conditions,suggest which type of mechanism compound 1 undergoes. Give reasons for youranswer. d. (6 marks) Draw a mechanism using curly arrows to show the formation of compound 2from compound 1 including any activated complex (transition state species) orintermediate. e. (5 marks) If the sodium methoxide is left out of the reaction mixture, compound 2 isformed in roughly equal amounts with another compound (compound 3). Suggest whatcompound 3 is and draw its structure. With reference to the mechanism of the reaction,explain how these two compounds (compounds 2 and 3) are formed under theseconditions. (You do not need to draw the mechanism for this reaction.)

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