5135

Compound 1 is a waxy solid melting a little above room temperature. It did not boil when a sample was place in an oil bath and the bath was raised to 200°. The compound did not dissolve in water, 5% NaHCO₃ or in 5% HCl, but did dissolve in 5% NaOH. It gave a solid when treated with a-naphthylisocyanate using a pyridine catalyst. Recrystallization of the solid derivative from hexane gave crystalline material, mp. 144.5-146°. Which of the following compounds is consistent with the data above?

Compound	mp (°C)	bp (°C)
2-methoxybenzaldehyde	38	245
benzophenone	48	305
4-oxopentanoic acid	33	246
2-methylphenol	34	202
4-bromophenol	64	238
4-methylaniline	43	200
2,6-dimethylaniline	11	216
3-phenyl-2-propen-1-ol	34	250

5203

Six test tubes, marked A, B, C, D, E, and F, respectively, contain acetophenone, cyclohexanol, benzaldehyde, p-cresol, benzoic acid, and cyclohexene, but not necessarily in that order. Using the results of the qualitative tests shown below, identify the contents of each test tube.

	A	B	C	D	E	F
Physical state	liquid	solid	liquid	liquid	solid	liquid
sol. H₂O	no	no	no	no	no	no
sol. 10% NaHCO₃	no	no	no	no	yes	no
sol. 10% NaOH	no	no	no	no	yes	yes
Br₂/CCl₄	decolor	decolor	no rx.	no rx.	no rx.	no rx.
2,4-DNP	no rx.	orange	no rx.	orange	no rx.	no rx.
Tollen’s mirror	no rx.	no rx.	no rx.	mirror	no rx.	no rx.
FeCl₃/alcohol	no rx.	no rx.	no rx.	no rx.	no rx.	red

A _____________________

B _____________________

C _____________________

D _____________________

E _____________________

F _____________________

5204

A drug whose physiological effects are similar to those of aspirin may be prepared by heating p-methoxybenzoyl chloride with an equimolar quantity of phenol in the presence of an excess of suitable organic base to act as a proton acceptor and solvent. Assuming that the reaction is not 100% complete, write a detailed experimental procedure for the workup and purification of this drug. The product is a white solid, mp 132°, insoluble in water, soluble in ether, alcohol, and hot benzene.

5378

Show a flow chart outlining the way in which extraction can lead to the separation of the following mixture: acetic acid, 2-heptanone, and p-cresol (4-methylphenol). Be specific and use chemical formulas.