11. a. Show how you would perform the following synthesis starting from the amine shown below (10 points) b. Based on your synthetic route, how many peaks would you expect to see in the reverse phase HPLC of the product assuming it is pure? (2 points) H₂N NH
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- Draw the major organic product(s) of the following reaction. .CI H20 NaOH • You do not have to consider stereochemistry. • If no reaction occurs, draw the organic starting material. When Sn1 & E1 pathways compete, show both the substitution and the elimination products. Separate multiple products using the + sign from the drop-down menu. • Do not include counter-ions, e.g., Na*, I", in your answer. ChemDoodle ve Show HintQ.2 a) Propose a mechanism for each of the following reactions. (10 Marks) i) K2CO3 HO- THE N- `NH2 i) ELOH/EtONa i) ii) CI ii) CH3COOHB. Determine the substrate and the nucleophile in each pair of reactants. Show the mechanism of the reaction through curved arrows and draw the final product. (B2) CI + + -OH н-о-н
- Consider the E2 elimination of 3-bromopentane with hydroxide. :Br CH3 product + Br+ H2O H CH3CH2 Complete the curved arrow electron-pushing mechanism and draw the structure of the organic product formed. H. Use three curved arrows to show the conversion to the product. Draw the organic product. Select Draw Rings More Erase Select Draw Rings More Erase H C H. Br : Br : H H II H H. : o:What would be the major difference between the IR spectrum of your aldol product and an IRspectrum of a mixture of vanillin and acetone? a) There would be two C=O stretches in the starting mixture, but not in the product.b) The C=O stretch in the product would be at lower frequency than acetone, as it is a highlyconjugated ketone.c) There would be an OH stretch in the starting mixture, but not in the product.d) Both a) and b)e) Both a) and c)37. (4 points). The following compound was obtained from cells, after supplying them with 1"C-labeled pyruvate. The positions containing 1"C atoms on the isolated molecule are indicated by an asterisk. Draw pyruvate below and circle the carbon(s) that was/were labeled in the experiment. (Scored number right minus number wrong.) COOH COOH *C = 0 C = 0 CH, *CH, COOH COOH
- Draw the major organic product(s) of the following reaction. 0 . You do not have to consider stereochemistry. • If no reaction occurs, draw the organic starting material. II... + • When SN1 & E1 pathways compete, show both the substitution and the elimination products. Separate multiple products using the + sign from the drop-down menu. . Do not include counter-ions, e.g., Na*, I, in your answer. /// ? H₂O ChemDoodle* Your answer is incorrect. Which synthetic route(s) would complete the reaction shown? Br ? 1 SO II O III O I and II Oland III OH + enantiomer HO Synthesis I: 1. NaCCCH3; 2. Na/NH3(1):3. OsO4; 4. NaHSO₂, H₂O Synthesis II: 2. NaCCCH3: 2. H₂, Lindlar's catalyst; 3. MCPBA: 4. aq. H₂SO4 Synthesis III: 1. NaCCCH3: 2. H₂, Pt: 3. MCPBA: 4. aq. H₂SO4C. Show the product formed in each step of the following synthetic sequence. CH2=CH2 HBr, H₂O2 H₂C=PPh3 Mg PCC DCM 1. 2. H3O+ H
- Draw the organic product of the following reaction (either enantiomer). Copy the SMILES code generated into the answer box. Remember that clicking the wedge a second time turns it into a hash. 1. BH3/THF 2. NaOH/H₂O₂/H₂O 8 N Br X NEW XR AD SMILES: % JSME Molecular Editor by Peter Erti and Bruno Bie Canonical SMILES If the tool does not appear, click this link.4. (3 points) Consider the reaction shown below. Assume that the acetone and benzophenone are in solution together, then base is added. H3C CH3 NaOH H3O+ EtOH, heat acetone benzophenone a. (1 point) Predict the crossed aldol product. Write the product in the box b. (1 point) If the concentration of the acetone was doubled, what is a potential undesired outcome? c. (1 point) If the order of addition was acetone, NaOH, then benzophenone, what is a potential undesired outcome?Which synthetic sequence will give the following overall transformation? how? (1) LDA / THF; (2) CH31; (3) H2 / Pd on C a. H2 / Pd on C b. (1) HBr; (2) CH3LI; (3) H2 / Pd on C C. (1) BH3 / THF; (2) H2O2: (3) CH3LI d. (1) Li / NH3liq): (2) CH3I Oe.