Test: GRE Subject Test: Chemistry

1.

A chemist carries out the synthetic scheme shown below.  Unfortunately, the first two reactions are incomplete, and a mixture of compounds A, B, and C is obtained after the second step. The chemist purifies this mixture by normal phase chromatography, using silica gel as a stationary phase and a 10:1 hexanes-diethyl ether (v:v) solution as an eluent. In what order would compounds A, B, and C elute off the column?

For each choice, the first compound to elute is listed first.

Mcat_1

B, A, C

C, B, A

A, C, B

C, A, B

B, C, A

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