Answer Happy

24. Provide the structure of the intermediate that is produced by the mechanism shown in Step 1 of the following scheme. Draw in the curved arrows on your intermediate that give the product of Step 2. 25. Draw in the curved arrows to show the mechanisms of Steps 1 and 2, and provide major organic product after Step 3 of the E1 reaction shown. e HⓇ phenyl butanoate H₂O

U 8 26. The following IR spectrum is produced by p-hydroxyacetanilide (aka - Tylenol). a. Which bond in the structure would produce the sharp peak at 3326 cm³¹? b. Which bond in the structure would produce the broad udder at 3165 cm³¹? c. Which bond in the structure would produce the peak at 1657 cm¹¹? ww N₂ 3326 cm¹¹ HO 3165 cm¹¹ 1657 cm 1500 M p

27. The following ¹H NMR spectrum is produced by p-hydroxyacetanilide (aka - Tylenol). Copy the structure of p-hydroxyacetanilide shown below onto your paper. On your paper, label each H on the structure with the letter(s) that corresponds with the appropriate peak in the ¹H NMR spectrum (Ha has been labelled for you as an example of how to do this). 11 HSP-43-745 Ha 1H 5 10 9 H₂ 1H S Ha or 8 HA 4H m 6 ppm 5 A W. 3 N. 2 He 3H S 1 O.

200 28. The following ¹3C NMR spectrum is produced by p-hydroxyacetanilide (aka- Tylenol). Copy the structure of p-hydroxyacetanilide shown below onto your paper. On your paper, label each C on the structure with the letter(s) that corresponds with the appropriate peak in the 13C NMR spectrum (Car have been labelled for you as an example of how to do this). 180 ▾ CDS-02-660 3 CA 160 140 of Gar HO 120 100 ppm 80 60 40 8 20 -O 0

29. Predict the number of signals/peaks expected in the 13C NMR spectrum of the compound shown below. H₂C CH3 CHS 30. Sketch a reaction coordinate diagram for the following multi-step reaction data. Be sure to properly label the axes, reactants, intermediate, products, and transition states. CH4 + Cl CH3 + Cl2 + HCl - Step 1: Ea= +17 kcal/mol and AH° = +4 kcal/mol Step 2: Ea = +4 kcal/mol and AH -109 kcal/mol - CH3Cl + Cl- 31. Which step in the previous question is the rate determining step (aka - rate limiting)? 32. Draw in the curved arrows for the SN2 reaction shown. Olmu NaOEt OEt 33. Why did the dash change into a wedge in the product of the previous question?

34. Draw in the curved arrows for each step of the cleavage of 2-ethoxypropane by HCI. Step 1 is protonation Step 2 is SN2 Step 3 is protonation Step 4 is SN2 HIC -~Y - 35. What always happens as a next step after a neutral nucleophile attacks something? a Ge