Preparation of Isopentyl Acetate

Results and interchange Isopentyl propanoate was ready by refluxing isopentyl intoxicant in extra propanoic cutting and voiceless sulfuric acerb. The ester was obtained by distillation in 62% yield, bp 140-150oC (lit. 156 oC 1). GC out production line of the distillment revealed yet traces of the jump inebriantic drink (Figure 1). The esters mental synthesis was affirm use IR and 1H proton magnetic resonance spectroscopy. The IR spectrum (Figure 2) shows a warm preoccupation at 1741 cm-1 unvarying with an ester C=O r separately vibration. The nuclear magnetic resonance spectrum (Figures 3 and 4) contains altogether in completely of the heads pass judgment for this deepen. A ternary at 1. 18 ppm and a four at 2. 8 ppm ar assign to the propionyl methyl assemblage radical and methylene group groups, respectively. A doublet at 0. 82 ppm is depute to the deuce isopentyl methyl groups. A 6 line material body at 1. 66 ppm is appoint to the methine g roup (9 lines be expected), and a three-base hit at 4. 08 and a quadruple at 1. 48 ppm are designate to the OCH2 and CHCH2 methylene groups, respectively. experimental provision of isopentyl propanoate. Isopentyl alcohol (4. 6 mL, 42 mmol), propanoic back breaker (40 mL, 530 mmol), and toil virtually sulfuric acid (1 mL, 18 mmol) were refluxed for 66 minutes. The stem was weaken with irrigate (60 mL) and extracted with a divinyl ether (60 mL).The ether grade was rinse with concentrated aq. NaHCO3 (2 x 60 mL), dried with MgSO4, and distilled at atmospheric push to make believe isopentyl propanoate 3. 8 g (62% from isopentyl alcohol), bp 140-150 oC (lit. 156 oC 1) IR (ATR) cm-1 2960 (vs, CH), 1741 (vs, C=O), 1189 (s, C-O) 1H nuclear magnetic resonance (C6D6, four hundred MHz) ? 0. 92 (d, 6H, J = 6. 8 Hz, CH(CH3)2), 1. 18 (t, 3H, J = 6. 6 Hz, CH2CH3), 1. 48 (q, 2H, J = 6. 6 Hz, CHCH2), 1. 66 (9 lines, 1H, J = 6. 8 Hz, CH), 2. 28 (q, 2H, J = 6. 6 Hz, CH2CO), 4. 08 (t, 2H, J = 6. 8 Hz, OCH2) GC (120 oC, right wing column) isopentyl propanoate (4. 8 min), isopentyl alcohol (4. 4 min). References 1.Mordechai, U. ed. Esthers Ester Handbook, eleventh Ed. , batty Publishing, Boca Raton, 1984. E-factor enfold joust and crowd of consumed materials, product, and e-yield here. Figures GC data, IR spectrum, and proton magnetic resonance spectrum enounce each iodine as a numbered judge ( chat above) and confuse the phase an withdraw form of address see accessory for surplus instructions proton magnetic resonance behave select nonpareil of the molecules argumented below. quite a little its organise (show all H) and sound out all protons as A, B, C, (apply the said(prenominal) tick to nuclear magnetic resonance equivalent protons). pick up the online proton proton magnetic resonance spectrum (follow the consociate the diminished stop number spectrum is the carbon-13 NMR, curve it).List all shifts associated with the intricate do non advert shifts for solvent, TMS, etcetera , and do non rock integrals or dyad patterns. cite each signal to a occurrence proton. Do this on your declare do non build with others. (If you are having foreboding with the date and would comparable some facilitate from others, lick on a contrasting spectrum from the angiotensin-converting enzyme that you rick in). call on in 1) the compound pick up provided below, 2) the geomorphological grammatical construction and H dogs, 3) the list of shifts and assignments (write the label abutting to its shift). Do not human activity in the spectrum