Which of the following is a key intermediate for Step 1 of the reaction shown in the box? A) C) OCH 3 LIAIH Step 1 OCH ₁ B) HCI, H₂O Step 2 OH OCH 3 OH OH

7) Assign partial charges on the Cl-Cl (polarized) below. This reaction proceeds through a three-membered ring halonium intermediate. The first step involves arrows similar to the carbene reaction above plus an additional arrow showing the Cl-Cl bond breaking. The second step is SN2 at the more substituted carbon. 8) Complete the following reaction by adding curved arrows, intermediates, and the expected products. St r :CI-CI: :CI: 9) Label the Mechanistic steps above and the halonium ion intermediate. Because the second step is similar to SN2 the halides add anti to each other.

On the molecules on the back page, circle and label all of the functional groups that you see (identified in the table above). Please note the following tips that may help you on this assignment: If a molecule contains –COOH, or a C double bonded to an O and single-bonded to an –OH, the functional group you circle is only the carboxyl, not a carboxyl, carbonyl, and hydroxyl separately). Phosphate groups are tricky – any P surrounded by 4 O’s is a phosphate – adjacent phosphates may share an O, and sometimes the O is in the form of OH. There is often shorthand that is used in drawing these structures – if you see a jagged line or ring structure, assume that carbon is at each corner. There may be ionized forms of the functional groups above (such as NH2 or NH3+) – these are the same functional groups. The order of the atoms in the functional group may be switched, depending on which side of the molecule it is on. For example, “—NH3” and “H3N—“  are the same thing.

Draw both resonance structures of the mnost stable carbocation intermediate in the reaction shown +. HBr • You do not have to conside stereochemistry Do not include anionic counter-1ons, e g., I, in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. in