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The NMR image is the data The following is a NMR of the reaction process over time including work up. , who +H CH OH

The NMR image is the data

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The following is a NMR of the reaction process over time including work up. , who +H CH OH , Acetic Acid HO 3-Methylbutanol (isopentyl alcohol) 3-Methylbutyl acetate (isopentyl acetate) CH CHE CH- TMS Product 3-Methylbutyl acetate - Distilled After NaHCO3 wash, salt extraction & dried ih we hul After H2O & NaHCO, wash H20 __ After reflux CH2-O- m O=COH Initial reaction mixture Acetic acid + 3-Methylbutanol CH (CH3-CH- CH2-OH CH2 - TMS Starting material OH 3-Methylbutanol, neat ih O=COH ola H.C OH Starting material Acetic acid, anhydrous O=CCH3 TMS 11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 -0.5 0.0 0.0 ppm 12. In the starting material 3-methylbutanol, neat, why is the OH peak showing up as a triplet? 13. The NMR for the Initial reaction mixture of acetic acid and 3-methylbutanol, why has the carbonyl OH peak shifted from 11.5 to ~9.5 and the OH peak at 5 is missing? 14. After reflux, is any acid or alcohol detected? 15. After water and NaHCO3 wash, why would the peak around 2 be shifted slightly to the right? What does this mean

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