Test 4 – ORG II (Lecture 4 - ORGII / Module 4 - ORGII): 5 points 1. Please predict the products for each of the following SNAr reactions. (1 point = 0.1 points each reaction x 10): KI NH2NH2 SNa IZ 9 8 10 Cl 7 CH3ONa t 1 NO₂ 6 2 NO₂ 5 Okt 3 4 1. NaOH 2. H3O+ i-ProNa NH₂ 2. Predict all the theoretical products for the following reactions. If no products are expected, please say NO REACTION: (1 point): https://doi.org/10.1021/jo01087a005 (a) (0.2 points) CI CI 1. NaNH2, NH3 (liq.) 2. H3O+ (b) (0.2 points) CI 1. NaNH2, NH3 (liq.) 2. H3O+ (c) (0.2 points) CI .CI 1. NaNH2, NH3 (lig.) 2. H3O+ (d) (0.2 points) CI 1. NaNH2, NH3 (liq.) 2. H3O+ (e) (0.2 points) CI 1. NaNH2, NH3 (liq.) CI 2. H3O+ 3. Propose an efficient synthesis for the following transformation (1 point): Hint: the most efficient synthesis has 5 steps (each step 0.2 points) Answer: z NO₂ 4. For each compound below, predict the number of signals in the expected 13C NMR spectrum (1 point): (a) (0.25 points) NO₂ НО, (b) (0.5 points) HO (c) (0.25 points) 5. Predict all possible products for the following reactions: (1 point): (a) (0.2 points) F3C 0=6=0 (b) (0.2 points) NO₂ oro (c) (0.2 points) CI CI (d) (0.2 points) O₂N. NO₂ CN CI 1. NaOH, 350 °C (e) (0.2 points) Br 2. H3O+ 1. NaOH, 80 °C 2. H3O+ Br₂ (2 equivalents) FeBr3 NH3 NO₂ 1. NaNH2, NH3 (liq.) 2. H3O+