(CHE 276) Organic Chemistry Lab
Fall 2011
Experiment 4: Separation of a Three Component Mixture by Extraction
Appendix C: Questions
Answers to questions should be typed and submitted in Appendix C of your Lab Report. Hand
written answers will not be graded. Supporting figures, if any, may be neatly hand drawn.
1. A student prepares Compound A in the organic lab. This product is known to contain an
impurity, Compound B. The student decides to separate the impurity from Compound A by
extraction.
O
O
OCH3
A
OH
B
a. The impure Compound A in dissolved in diethyl ether and transferred to a seperatory funnel.
What reagent should then be added to effect removal or the compound B? Be specific.
b. After the extraction, Compound A is dried and isolated. How can TLC be used to determine if
the purification of compound A by extraction was a success?
2. A mixture of compounds below is dissolved in diethyl ether and transferred to a separatory
funnel. Excess 10% HCl is added and the contents of the funnel are mixed. When the layers
separate, what compound(s) are found in the top layer? Clearly explain your reasoning.
O
NH2
OH
pentanoic acid
naphthalene
isobutylamine