21.A researcher was asked to prepare butylbenzene from benzene. They chose to use chlorobutane and a Lewis acid catalyst (shown below), but was surprised to find that butylbenzene was not formed. butylbenzene? Provide a complete curved-arrow mechanism that accounts for the formation of the unwanted product. What isomeric product was formed instead of AIC butyl benzene not formed! undesired product After realizing their eror, the researcher was able to make butylbenzene from benzene in a multi-step process. Outline this synthetic sequence in the space below (no mechanisms, please).

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
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21.A researcher was asked to prepare butylbenzene from benzene. They chose to use
chlorobutane and a Lewis acid catalyst (shown below), but was surprised to find that
butylbenzene was not formed.
butylbenzene? Provide a complete curved-arrow mechanism that accounts for the
formation of the unwanted product.
What isomeric product was formed instead of
AIC
butyl benzene
not formed!
undesired product
After realizing their error, the researcher was able to make butylbenzene from benzene in a
multi-step process. Outline this synthetic sequence in the space below (no mechanisms,
please).
Transcribed Image Text:21.A researcher was asked to prepare butylbenzene from benzene. They chose to use chlorobutane and a Lewis acid catalyst (shown below), but was surprised to find that butylbenzene was not formed. butylbenzene? Provide a complete curved-arrow mechanism that accounts for the formation of the unwanted product. What isomeric product was formed instead of AIC butyl benzene not formed! undesired product After realizing their error, the researcher was able to make butylbenzene from benzene in a multi-step process. Outline this synthetic sequence in the space below (no mechanisms, please).
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