2) (1 point/box) Complete the following syntheses with the missing reagents and major products after each step to make the desired final product shown. Count your carbons! Show the correct molecular geometry and show stereochemistry when needed. (5 pts.) Хо Br Hint: SN2

Part A CH3CH2 CH3 C=C Br₂ CH2Cl2 CH3 CH2CH3 Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Ad appropriate stereochemistry by choosing the dashed or wedged buttons and then clicking a bon □ D C ® Q® H± 12D EXP. CONT. י • Α [1] Δ Submit Request Answer Marvin JS by Chemaxon H с N So о CI Br I P F

4. Regioselectivity Draw the major product formed for each reaction. Assume the reactions are irreversible. Include stereochemistry when products contain stereocenter(s). (a) Draw only the substitution product. Both elimination and substitution occur here. Hac Br CH₂OH (c) (b) CH3 CH3 Br H NaOCH3 80 °C 1 equiv CH3Li then

5. Predict the structure of the product formed (with correct stereochemistry) for each of following pericyclic reactions. a) b) .CI c) CH2 [1.5)-H A -CH3 d) [3,31-C A CH, hv CH CH, hv CH; [12 marks