Question

6. Consider the following substitution reaction: (10) Pr NaN NaBr MDMSOM (a) Determine whether this reaction proceeds via an SN1 or SN2 process. (b) Draw the mechanism of this reaction. (c) What is the rate equation of this reaction? (d) Would the reaction occur at a faster rate if the concentration of cyanide were doubled? (e) Draw an energy diagram of the reaction above.

Answer 1

G. Given substitution geaction CY i NOCN NOCH , traer HaST DMSO ca) Determine whether this reaction proceeds via SN (On SNY reaction The reaction proceeds yra SA mechanism Because In this reachon we observed PSN Invez se on product A chinal rolecule Onden Substitution produce Inversion of configuration. Only follows SN mechanism ISSN ero Backsede s-configuration R-configuration least priority groop in above the plane In SAP reaction extenal nucleophile aHacks Pn back side of the molecule then reaction produce inversion of product b2 Doraw the mechanfsm of the reaction rechanism NacN I HOB Br 1 fash Transition state

In SN reaction product formation via a transition State intermediate Learing of Bromine and attacking of Cyanide yon at the same time in Chinal carbon produce a trigonal planan transition state Nucleophile Cyanide altack back side by change for the configuration. (C) Lhar 95 the rare equation of this reaction. In mechanism ib. frost step 95 Slow Step and rate determining step. In this step Yeaction in volves botn alicyl bromide and Nucleophile then state of reaction depends Concentration of reactant and concentration of Nucleophile Rate [Reactant;'c Nacn]' Rate de [S-2 Bebmo pentane Nack]' Rate = k CS-2 Bromo pentane]'c Naca' Where kis rate constant The order of reaction with respect to reactant and Nueleophile 2. : (el) would the reactron occur at to faster rate of the concentration of cyanide son Where doubled.

The reaction rate also depends the concentration of Cyanide then we an Grease the concentration of cyanide the rate of reaction also will be an creases Concentration of cyanide in Grease doubled. reaction rate also an Crease 2 times | (C) Draw an energy diagram of the tabove reaction ransition state La Energy reactant free energe Chance product Reaction Co-Ordinale A-free energy diagram Sir reaction. for a hypothetical