Consider the starting material and determine the total number of carbonyl containing groups that are present. Ignore the TIPS and TROC protection groups in your answer.
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3. (4pts) Provide the structure of the unknown ketone/aldehyde starting material that would produce the following HNMR spectrum: 3H, Triplet 2H, Triplet 3H, Triplet 2H, Quartet 2H, Complex multiplet resembling a sextet 2H, Doublet 2H, Doublet PPM 4. (4pts) Students are asked to "wash" their reaction solution, as well as, the organic extraction layers. What is/are the most likely impurities that are removed during these washing steps? Provide a balanced equation for the overall reaction to help answer this question below. Hint – track your boron:
Shyam P.
Propose structures for molecules that meet the following descriptions. Assume that the kinds of carbons $\left(1^{\circ}, 2^{\circ}, 3^{\circ}, \text { or } 4^{\circ}\right)$ have been assigned by DEPT-NMR. (a) $\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O} ;$ IR: $1715 \mathrm{cm}^{-1} ;^{13} \mathrm{C}$ NMR: $8.0 \delta\left(1^{\circ}\right), 18.5 \delta\left(1^{\circ}\right), 33.5 \delta\left(2^{\circ}\right)$ $40.6 \delta\left(3^{\circ}\right), 214.0 \delta\left(4^{\circ}\right)$ (b) $\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O} ;$ IR: $1730 \mathrm{cm}^{-1} ;^{13} \mathrm{C}$ NMR: $22.6 \delta\left(1^{\circ}\right), 23.6 \delta\left(3^{\circ}\right), 52.8 \delta\left(2^{\circ}\right)$ $202.4 \delta\left(3^{\circ}\right)$ (c) $\mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O} ;$ IR: $1680 \mathrm{cm}^{-1} ;^{13} \mathrm{C}$ NMR: $22.9 \delta\left(2^{\circ}\right), 25.8 \delta\left(2^{\circ}\right), 38.2 \delta\left(2^{\circ}\right)$ $129.8 \delta\left(3^{\circ}\right), 150.6 \delta\left(3^{\circ}\right), 198.7 \delta\left(4^{\circ}\right)$
11. Quantitative conversion to enolate when exposed to sodium ethoxide. 1) Ethyl malonate 2) Nitromethane 12. Water leaves after step ____ of imine formation. 1) Five 2) Six 13. Dehydration after Aldol condensation requires heat and ____ conditions. 1) Acidic 2) Basic 14. Goes through a charged iminium intermediate. 1) Acylation reduction of an amide with LAH 2) Reductive amination with NaBH3CN 15. One equivalent of dimethyl heptanedioate reacting with 1. Catalytic sodium methoxide 2. "Take Home" conditions produces one equivalent of cyclohexanone. 1) True 2) False 16. Positive during ketal formation of acetone with ethylene glycol: 1) ΔH 2) ΔS 17. Big Molecule. Vasopressin (modified) is a hormone that regulates blood pressure and solute concentration. a) How many organic fragments are produced after treatment with "Take Home" conditions? (If a molecule is produced more than once count it each time in your total. Remember: water, carbon dioxide and ammonia are not organic.) b) Provide the name of the smallest organic fragment generated after "Take Home" conditions.
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