synthesis of 1- bromobutane dissolve 1.33 g sodium bromide in 1.5 mL distilled w

Question

synthesis of 1- bromobutane dissolve 1.33 g sodium bromide in 1.5 mL distilled water, using a stir bar. Add 0.80 g 1-butanol. Place water-condenser on round bottom flask. Turn on water, and then drop-wise add 1.1 mL concentrated sulfuric acid to this solution. Once you have finished adding the chemicals, heat to reflux and reflux for 40 minutes Show an electron pushing mechanism for the formation of the two unwanted organic byproducts from the reaction (hint: the two byproducts are not water and NaHSO4) (4)

Explanation / Answer

by product 1: dibutyl ether reactions leading for its formation.. Protonation of the OH allows H2O to be the leaving group in the SN2 reaction. C4H9OH + H+ C4H9O^+H2 + HSO4- C4H9O^+H2 + Br- ---> C4H9Br + H2O bromobutane product C4H9O^+H2 + HOC4H9 ---> C4H9-O^+(H)-C4H9 C4H9-O^+(H)-C4H9 C4H9-O-C4H9 + H+ dibutyl ether product byproduct 2: 1-butene CH3CH2CH-CH2-O^+H2 where one of the CH2 H's on carbon 2 .............| .........................is emphasized. .............H Some base in the system (and they are all weak bases under these strongly acidic conditions), perhaps another molecule of butanol, then removes the H and the electron pair holding it on the C falls between carbons 1 and 2 with simultaneous loss of H2O to give CH3CH2CH=CH2 + CH3CH2CH2CH2-O^+H2

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