SOLUTIONS Hour Exam #2 Name SOLUTIONS (please both print and sign your name) Official Recitation Instructor Directions: Closed book exam, no books, notebooks, notes, etc. allowed. Calculators are not permitted for this exam. However, rulers and molecular model sets are permitted. Please read through the entire exam before beginning in order to make sure that you have all the pages and in order to gauge the relative difficulty of each question. Budget your time accordingly. Show all of your work if you wish to receive partial credit. You could have 7 pages total. 5 exam pages including this page and 2 blank pages for scratchwork. Question: Grader: / 64 points / 18 points / 18 points Total: / 100 points 1 (64 points total, 4 points each) In each box below, draw the structure of the major product of the reaction. Indicate relative stereochemistry where appropriate.1 If no reaction occurs, put a large2 X in the box. (Note: "D" = deuterium, "H) [Reaction schemes a-g as described below] Reaction Schemes: a. [Starting material: Deuterated benzene ring with -CH=CH-CH3 group] + [Reagent: KMnO4 / H2O / heat] → [Product: Benzene ring with -COOH group. Deuterium is retained.] b. [Starting material: Cyclohexene with -CH3 and -COOCH3 groups attached] + [Reagent: H2 / Pd catalyst] → [Product: Cyclohexane ring with -CH3 and -COOCH3 groups attached. Stereochemistry is indicated.] c. [Starting material: Bromobenzene] + [Reagent: 1. NaOH / 2. Δ] → [Large X in box] d. [Starting material: Bromocyclohexane] + [Reagent: 1. NaOH / 2. Δ] → [Product: Cyclohexene] e. [Starting material: Cyclohexene] + [Reagent: 1. O3 / 2. (CH3)2S] → [Product: OHC-(CH2)4-CHO ] f. [Starting material: Cyclohexanone] + [Reagent: NaBH4 / CH3OH] → [Product: Cyclohexanol with stereochemistry indicated.] g. [Starting material: Cyclohexanone] + [Reagent: Ph3P=CH2] → [Product: Cyclohexene with exocyclic double bond CH2]