1. (30 points) Provide a complete, arrow-pushing mechanism to justify all the products in the reaction below. Label your mechanism as SN1, SN2, E1, or E2. Br NaOMe major + minor + minor

1. (10 points) Complete the reaction scheme below. Show all reagents and intermediates. No reaction is a possible answer. Do not neglect stereochemistry. NaCN DIBAL Br A "OCH3 (sodium cyanide)

Predict the major product of the given reaction and then draw a reasonable mechanism for the product formation using appropriate curved arrow notation. Part 1: OH H2SO4 (aq) view structure Part 2 out of 4 H,0 H,SO4 HSO, HO finish structure . draw structure . H;O*

(3) Mechanism. Provide the mechanism for the following reaction. HO OH Он |-0 HO Он NaOH, Н2О но HO Он HO Он

3. Show a mechanism for the following reaction. Q.XX NO₂ NO₂

4.(15 points) Draw the mechanism for the reaction below. © All rights reserved. PBr3 OH OH Br2 Br

Please Explain.

4. (10 points) Complete the reaction scheme below. Show all reagents and intermediates. No reaction is a possible answer. LDA lodomethane CH3 H H

iii) 10. For each of the following reactions, provide the structure of the major product and circle the predominant mechanism. Indicate the stereochemistry where necessary. VII) E1 E2 SN1 SN2 E1 E2 SN1 SN2 NaSH DMF H* CH3OH Br (CH3)3COK (CH3)3COH OH iv) HBr viil) E1 E2 E1 E2 SN1 SN2 SN1 SN2

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. CH₂CH₂CH3 НО. Provide a detailed, step-by-step mechanism for the reaction shown below. 1.03 2. (CH₂)₂S Br₂