4. Write a complete arrow-pushing mechanism for the following reaction under acid- catalyzed conditions + CH3CH2OH H3C H

10. practice q 10 Compound Free Energy HO A A reacts with B in the presence of sodium hydride to give C as a major product. NH₂ Ph B ŌSO₂CF3 NaH, THF a) Provide a detailed mechanism for the formation of C and draw it in the box above. ( C b) Draw the reaction coordinate diagram of that reaction. Indicate with an arrow the rate- determining step of the reaction then draw its transition state: Reaction Coordinate c) The reaction rate observed was 5 x 10-2 M.s¹ when the concentrations of A and B were 0.2 M and 0.1 M respectively. Determine the rate of this reaction when the concentration of A and B are now 0.3 M and 0.2 M respectively. Show your work.

Answer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrows

Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br: