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8. (15 pts) Owing to their structural similarity, separation of mixtures of organic
compounds (such as the isomers 1-t-butyl-, 3-t-butyl-
, and 4-t-butylcyclohexene)
often proves difficult. Silica gel chromatography, however, can be used with some
success provided that sufficient silica gel is used to provide optimal separation.
Consider the TLC plate pictured at right after developing and UV
visualization. If, prior to development, lanes A and B were spotted with 1-
t-butylcyclohexene and lanes B and C spotted with 4-t-butylcyclohexene,
which of the following are true? Circle the CORRECT response (T or F),
then in the space provided, explain your reasoning.
TF
1-t-butylcyclohexene elutes slower
than 4-t-butylcyclohexene
A B C
The Rf for both compounds is equal
T F
I F
• 4-t-butylcyclohexene is more polar
than 1-t-butylcyclohexene
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