5) Provide the expected mechanism for the following reaction. Please show all intermediates and use arrows to show the movement of electrons (you do not have to show transition states). (1 pt) ii CI NaOH (2 equiv)

Consider the reaction below. If the concentration of the nucleophile is doubled, the rate of the reaction will If the concentration of the alkyl halide is doubled, the rate of the reaction will H₂O x CI OH (c) double, not change (d) triple, triple (a) not change, double(b) double, double (e) not change, not change

OH OH ∞∞ BF3 Et₂O This reaction takes place via a pinacol rerrangement. Please, draw curved arrows to show the movement of electrons in this SPECIFIC step of the reaction mechanism. +BF3 HO: :OH OH (BF3OH)

1. OH ??? Br + B ОН For the above reaction identify the catalyst and reagents and also show the catalytic cycle.

In the following reaction CH,CH,CH,CI Anhy AICI, B (Major) Red hot A Iron tube HC = CH The product B is CH,CH,CH, CH,CH, CH, -CH, CH CH, CH,CH, CH,

The accepted mechanism for a rearrangement reaction is shown below. "Q Ph (1) (ii) Ph Ph HO™ fast Ph Ph HO O™ slow Ph aufae .Ar² LOH HO™ fast Draw a curly arrow mechanism for this transformation. Sketch an energy profile for this reaction, showing approximate relative energies for the reactants, intermediates, transition states, and products. HQ Ph (iii) When DO™ was used as the reagent, the rate of product formation was same as for HO™. Explain why this result shows that the third step is fast and cannot be rate-determining. Ph (iv) Write the predicted rate equation for this mechanism, and show how it was derived. (v) The starting diketone may have two different aryl groups, as shown below. Propose a ¹³℃ labelling experiment that would allow you to distinguish which of the two aryl groups had migrated in this situation. OH AR²0- Ar¹ C C

Draw all the intermediates formed for the reactions shown. (Hint: There are five intermediates for the first reaction and two for the second reaction, and the final product shown is not counted, of course.) LOH OH 0 HO H+ за

Mechanism: A reaction mechanism for the following reaction is shown below. H+ CEN CEN: N-H || -C-OH H₂O, H* Step 1 wand woled mot ozsm E Step 3 N-H C-OH C=N-H Step2 C=N-H H-O-H H₂O motno vgiene fesrigid onlt to smotnos -C=N-H a) The overall reaction is an example of b) Step 1 is c) Step 3 is d) Draw in the curved arrows for each step. e) Identify the nucleophiles and electrophiles where appropriate. f) Fill in the reaction energy diagram. H₂O: rate determining step to noipojovo hamwell sit 5(emise erit voittons 10) vanas mi sdgin al rainW di of E^ reaction progress →

102. The major products A and B in the following reaction sequence are CHO Br Br (i) PPh3 (ii) NaH (A) NaH OH (B)

NH3(g) + HCIO4(1) E→ NH,CI0,(s) A B C D Ep E, Ep - R P R P R R Reaction Path Reaction Path Reaction Path Reaction Path A