Extraction and Distillation (5C)

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MCAT Chemical and Physical Foundations of Biological Systems › Extraction and Distillation (5C)

Questions 1 - 10
1

A neutral metabolite M is extracted from 100 mL of water into an immiscible organic solvent with $K = \frac{M{org}}{M{aq}} = 4$. The lab can perform either (i) one extraction with 100 mL organic solvent or (ii) two sequential extractions with 50 mL organic solvent each, combining the organic layers. Based on the partitioning principle, which statement is most consistent with expected recovery of M?

Option (ii) yields higher recovery because re-equilibration with fresh solvent can remove additional solute each time.

Option (i) yields higher recovery because a larger single volume always extracts more than multiple smaller volumes.

Both options yield identical recovery because $K$ fixes the fraction extracted regardless of procedure.

Option (ii) yields lower recovery because combining organic layers decreases the effective partition coefficient.

Explanation

This question tests understanding of multiple versus single extractions in liquid-liquid partitioning. The partition coefficient K = 4 means the solute is 4 times more concentrated in the organic phase at equilibrium. Mathematical analysis shows that multiple extractions with smaller volumes extract more total solute than a single extraction with the same total volume. This occurs because fresh solvent in each extraction can remove additional solute from the aqueous phase. Choice B is correct because sequential extractions with fresh solvent portions allow re-equilibration and removal of more solute each time. Choice A is incorrect because it contradicts the mathematical principle that multiple extractions are more efficient. To maximize extraction efficiency, always perform multiple extractions with smaller volumes rather than one large extraction.

2

A compound W is distributed between two immiscible phases, with $K = \frac{W{org}}{W{aq}} = 5$. In an extraction, the organic layer volume is much smaller than the aqueous layer volume. Based on partitioning principles, which statement is most consistent with the effect of using a very small organic volume?

Organic volume affects only color intensity, not extraction extent

A small organic volume forces $K$ to decrease because $K$ depends on phase volumes

A small organic volume guarantees complete extraction because W prefers the organic phase

The organic phase can become relatively concentrated in W, but total moles extracted may be limited by its small volume

Explanation

This question tests understanding of phase volume effects on extraction. With K = 5, compound W prefers the organic phase. However, using a very small organic volume means limited capacity to hold W. While the organic phase concentration can become quite high (5x the aqueous concentration), the total moles extracted are limited by the small volume. Choice A is correct because it recognizes both the concentration effect (K determines ratio) and the capacity limitation (small volume limits total extraction). Choice C is incorrect because favorable K doesn't guarantee complete extraction with insufficient organic volume. Consider both partition coefficient and phase volume ratio when designing extractions.

3

A lab purifies an essential oil component E from plant material by first extracting into a nonpolar solvent, then removing the solvent by distillation. E decomposes near 180°C, while the solvent boils at 40°C (1 atm). Based on boiling point differentiation, which approach is most consistent with minimizing decomposition of E during solvent removal?

Distill off the solvent at or near its boiling point, leaving E in the flask

Heat the mixture to 180°C so E vaporizes and can be collected pure

Freeze the mixture so the solvent sublimes and carries E with it

Use chromatography in the condenser to separate E from solvent vapor

Explanation

This question tests understanding of temperature-sensitive compound purification. With E decomposing at 180°C and solvent boiling at 40°C, distilling the solvent at its boiling point keeps the temperature well below E's decomposition point. The nonvolatile E remains in the flask while the volatile solvent distills off. Choice A is correct because it uses the large boiling point difference to separate components while avoiding decomposition. Choice B is incorrect because heating to 180°C would decompose E rather than purify it. For thermally labile compounds, remove solvents by distillation at the solvent's boiling point or under reduced pressure for even lower temperatures.

4

A lab distills a mixture of two volatile solvents, X (bp 78°C) and Y (bp 82°C), at 1 atm. The goal is to obtain X at high purity. Based on the principle of fractional distillation, which setup change is most consistent with improving separation for these close boiling points?

Replace the fractionating column with a shorter, empty column to reduce holdup

Use a fractionating column packed to increase surface area and repeated equilibration

Increase the heating rate strongly so both components boil together and separate faster

Switch to gravity filtration to separate X from Y based on particle size

Explanation

This question tests understanding of fractional versus simple distillation for close-boiling mixtures. When components have similar boiling points (78°C vs 82°C), simple distillation provides poor separation because the vapor contains significant amounts of both components. Fractional distillation uses a packed column to create multiple vapor-liquid equilibration stages, progressively enriching the vapor in the lower-boiling component. Choice B is correct because increased surface area and repeated equilibrations improve separation efficiency. Choice A is incorrect because reducing column length decreases separation ability. To separate close-boiling liquids effectively, use fractional distillation with adequate theoretical plates rather than simple distillation.

5

A lab performs liquid–liquid extraction of a neutral steroid from 20 mL water into 10 mL hexane. The partition coefficient is $K = \frac{S{hex}}{S{aq}} = 10$ at this temperature. Based on the partition coefficient principle, which change would be expected to increase the fraction of steroid remaining in the aqueous layer after equilibrium is reached?

Agitate more vigorously so the steroid chemically reacts with water

Decrease $K$ by switching to a more polar organic solvent than hexane

Increase the hexane volume while keeping water volume constant

Perform the extraction at lower pressure to reduce the boiling point of hexane

Explanation

This question tests understanding of factors affecting extraction efficiency based on partition coefficients. The partition coefficient K = 10 indicates the steroid strongly prefers hexane over water. To increase the fraction remaining in water, we need to decrease the effective extraction into hexane. Choice A is correct because using a more polar organic solvent would decrease K, making the steroid less preferentially extracted and leaving more in the aqueous phase. Choice B would actually extract more steroid by increasing the organic phase volume. Choice C incorrectly relates pressure to extraction efficiency, while Choice D suggests an irrelevant chemical reaction. Remember that partition coefficients depend on the nature of both solvents and can be manipulated by changing solvent polarity.

6

A compound X is extracted between octanol and water to estimate lipophilicity. The measured partition coefficient is $K = \frac{X{oct}}{X{aq}} = 0.20$ for the neutral form. Based on this value, what conclusion can be drawn about X under these conditions?

X will be best separated from water by simple distillation because $K<1$

X preferentially partitions into water, consistent with relatively higher hydrophilicity

X preferentially partitions into octanol, consistent with high lipophilicity

X must be ionic because partition coefficients are only defined for ions

Explanation

This question tests interpretation of partition coefficient values for predicting compound properties. A partition coefficient K = 0.20 means the concentration in octanol is only 0.20 times that in water, indicating the compound prefers the aqueous phase. Since octanol represents a lipophilic environment and water represents a hydrophilic environment, this low K value indicates relatively higher hydrophilicity. Choice B correctly identifies this relationship. Choice A incorrectly interprets the K < 1 value as favoring octanol. Choice C confuses extraction with distillation, which are different separation techniques. Choice D is incorrect because partition coefficients apply to neutral molecules, not just ions. To interpret partition coefficients correctly, remember that K > 1 indicates lipophilicity while K < 1 indicates hydrophilicity.

7

A student attempts to separate a mixture of acetone (bp 56°C) and water (bp 100°C) using simple distillation at 1 atm. The mixture is heated slowly, and vapor is condensed and collected. Based on boiling point differentiation, which outcome is most consistent with simple distillation?

The distillate collected early is enriched in acetone relative to the original mixture

Water distills first because it has stronger hydrogen bonding and thus higher vapor pressure

Acetone cannot be separated by distillation because it is miscible with water

The distillate composition is identical to the boiling flask composition at all times

Explanation

This question tests understanding of simple distillation based on boiling point differences. In simple distillation, the component with the lower boiling point (higher vapor pressure) will be enriched in the vapor phase and thus in the distillate. Acetone (bp 56°C) is much more volatile than water (bp 100°C), so the initial distillate will be enriched in acetone. Choice A correctly states this outcome. Choice B is incorrect because distillate composition changes over time as the more volatile component is depleted. Choice C incorrectly relates hydrogen bonding to vapor pressure - stronger hydrogen bonding actually decreases vapor pressure. Choice D incorrectly suggests miscibility prevents separation, when in fact distillation separates based on volatility, not miscibility. Remember that lower boiling point means higher vapor pressure at a given temperature.

8

A mixture contains three volatile components with normal boiling points at 1 atm: P (60°C), Q (90°C), and R (120°C). A fractional distillation is begun and fractions are collected as the head temperature stabilizes near plateaus. Which collection order is most consistent with boiling point differentiation?

Q first, then P, then R because the middle boiling point component equilibrates fastest.

R first, then Q, then P as the temperature decreases over time.

P first, then Q, then R as the temperature increases over time.

All three co-distill together in a constant ratio because fractional distillation prevents enrichment.

Explanation

This question tests understanding of fractional distillation collection order. In fractional distillation, components are collected in order of increasing boiling point as the head temperature rises through distinct plateaus. The lowest boiling component P (60°C) distills first when the head temperature stabilizes near 60°C, followed by Q (90°C) at its plateau, and finally R (120°C). Choice B correctly identifies this P-Q-R order with increasing temperature. Choice A reverses the order, incorrectly suggesting high-boiling components distill first. Remember that fractional distillation separates based on volatility differences, with more volatile (lower boiling) components collected first.

9

A researcher performs liquid–liquid extraction of a neutral metabolite M between water and hexane. The partition coefficient is defined as $K=\frac{M{hex}}{M{aq}}$ at equilibrium. If the experiment is repeated with the same total amount of M but the hexane volume is doubled (water volume unchanged), what outcome is most consistent with the definition of $K$?

No redistribution occurs because partitioning depends only on the initial concentrations, not equilibrium.

The equilibrium concentrations adjust, but $K$ remains the same at the same temperature.

The value of $K$ increases because more hexane is available to dissolve M.

The value of $K$ decreases because dilution in hexane lowers $[M]_{hex}$.

Explanation

This question tests understanding of partition coefficients as equilibrium constants. The partition coefficient K is a thermodynamic constant that depends only on temperature, not on volumes or initial concentrations. When hexane volume is doubled, more total metabolite M will transfer to the hexane phase, but the ratio of concentrations [M]hex/[M]aq at equilibrium remains constant. Choice C correctly states that equilibrium concentrations adjust while K remains unchanged. Choice A incorrectly suggests K increases with volume, confusing the equilibrium constant with the total amount extracted. To avoid errors, remember that equilibrium constants like K are intensive properties that don't change with system size.

10

A student attempts to separate a mixture of acetone (bp 56°C) and water (bp 100°C) by simple distillation at 1 atm. The distillate collected early in the run is analyzed. Which result is most consistent with the principle of simple distillation based on boiling point differences?

The early distillate has the same composition as the starting mixture because boiling points do not affect vapor composition.

The early distillate is enriched in water because water has stronger hydrogen bonding.

The early distillate is enriched in acetone relative to the starting mixture.

The early distillate is enriched in acetone only if a separating funnel is used instead of a condenser.

Explanation

This question tests understanding of simple distillation based on boiling point differences. In distillation, the component with the lower boiling point vaporizes more readily and enriches the vapor phase. Acetone (bp 56°C) is more volatile than water (bp 100°C), so the early distillate will be enriched in acetone. Choice A correctly identifies this enrichment of the lower-boiling component. Choice B incorrectly suggests water would distill first despite its higher boiling point, confusing intermolecular forces with volatility. Remember that in distillation, lower boiling point means higher vapor pressure at a given temperature, leading to preferential vaporization.

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