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Electronegative and Steric Hindrance Effects on Synthesized Esters By Katherine Edmonds Introduction Esters are made when an acid and an alcohol are mixed The reaction causes the oxygen and hydrogen atoms to pair off forming H20 leaving the rest of the compound to form the ester The theory is that if a more electronegative element was added to the compound it could increase the electronegativity in the whole molecule and the ester could form more rapidly The idea is that if you use a 3bromo1propanol alcohol mixed with ethanoic acid the bromine should create enough electronegativity so that the ester would form with more quantity and speed This should effect the formation more than steric hindrance because the bromine is attached to the third carbon hence all the movement from steric hindrance shouldnt cause bulkiness Bromine is used because it is a very electronegative atom and should act as a catalyst by speeding up the reaction rate Experimental Synthesis of 3-bromopropyl acetate 3- Bromo-1-propanol11g 117mmol was added to two molar equivalents of ethanoic acid 13992g 2332mmol 3 drops of H2SO4 was added per every gram of the alcohol It was refluxed for 30 minutes and allowed to cool overnight The room temperature mixture was placed into a seperation funnel where it was rinsed twice with distilled H2O discarding as much of the aqueous layer as possible It was then rinsed with 15 to 20 mL of NaHCO3 letting the pressure buildup escape at routine intervals until there was no more excessive pressure This aqeous layer was tested with lithmus paper and was decided to be neutral It was rinsed again with distilled H2O and once again with the NaHCO3 It was then dried over 178g of MgSO4 The mixture was distilled and was discovered to have an 82 yield Density of 1489715 and a bp of 1055C literature 8027 NMR CDCl3300MgHz 207797ppm s3HCH3 218188 m2HCH2 350514 t2HCH2 420740 t2H CH2Br
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