A researcher was attempting to make an alkyl bromide viaelectrophilic addition t

Question

A researcher was attempting to make an alkyl bromide viaelectrophilic addition to an alkene. She asked her researchassistant to carry out the synthesis using diethyl ether as thesolvent. The assistant placed the appropriate mass of3,3-dimethyl-1-butene in the diethyl ether solvent then he addedHBr. He isolated the product and ran a proton NMR spectrum on it.The spectrum that appeared on the screen was not the one theassistant was expecting. Below is the spectral data for theproduct. triplet @ delta 3.2, triplet @delta 1.7,singlet @ delta 0.9 with integration ratios 2:2:9, respectively Draw the structure of the product that was characterized by protonNMR. Top of Form Bottom of Form Top of Form When the assistant asked the researcher why the spectrum wasdifferent from the one he predicted, the researcher replied: Bottom of Form you did not wait long enough for thereaction to proceed and all you did was isolate the startingalkene you forgot about the possibility ofcarbocation rearrangement you did not take into consideration theeffect of the alkene pi-bond you must have used old diethyl ether thatwas contaminated with peroxides I have no idea where to start, so any help will be great. Iwill rate!

Explanation / Answer

Anybody? I still have time to do this.

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