Toronto Metropolitan University

CHY 142

Section 1: General (50 marks) 1. Which of the above structures would undergo the fastest Sn2 reaction when reacted with NaOH in a polar aprotic solvent? 2. Which of the above structures would undergo the fastest E2 reaction when heated with NaOEt in a polar aprotic solvent? 3. Which of the above structures would react fastest with NaOMe? 4. Which of the above structures would undergo the fastest hydrogenation using hydrogen on a palladium catalyst? 5. Which of the above structures would undergo the fastest Sn1 reaction when treated with iso-propanol? 6. Which of the above structures would undergo the fastest E1 reaction when heated with H2SO4? 7. Identify the chiral carbons in molecules A-O (use an asterisk *). 8. Which of the above structures would undergo the fastest radical bromination using Br2 and light in DCM? 9. Which above structure(s) is (are) generally considered to be polar aprotic solvent(s)? 10. Which structure above would react fastest with NaBH4 in ethanol? I J Br A B C G OTs H D E F Br Br Br OH O N K L M N O NH3 OH OH OTs I L O B J G B K D