5. Draw the mechanism of the following reaction (students need to draw arrows, intermediate, and products. Also, students need to show stereo configuration by using wedge and dash bonds for intermediates and products.) The major product of the following reaction exists as four stereoisomers. Show all hydrogen atoms in the structures. (you don't need to draw wedge and dash bonds for C-H bonds of CH2 groups in the ring). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between stereo isomers. (se vare et sub D Br₂ H₂O (excess) H

2. For the following nucleophilic substitution reaction: NaOC(CH3)3 CH3 'CH3 CH3 a. Draw the first transition state (TS1), the reaction intermediate, and the second m transition state (TS2) in the labeled boxes. Make sure to show any formal charges, unfilled p-orbitals, and correct stereochemistry. TS₁ 41001 Intermediate ogmos TS2 amond- b. Which of three molecules you drew for part 'a' is lowest in energy? Write your answer in the box below. c. Draw the product(s) of the nucleophilic addition reaction shown. Make sure to use wedged and dashed lines to clearly show the resulting stereochemistry at each chiral center. If there is more than one possible product, draw one in each box - if not, leave one box blank. CH3 Br + NaOC(CH3)3

Stereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the struct a compound that is a stereoisomer of trans-1,2-dibromocyclobutane. (Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.) • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • In cases where there is more than one answer, just draw one. Hox Sn [F ? ChemDoodle

Is the answer I selected correct?