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Chapter 11: Problem 120

For each of the following pairs, predict which substance is more soluble in water. a. \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) or \(\mathrm{NH}_{3}\) b. \(\mathrm{CH}_{3} \mathrm{CN}\) or \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}$ d. \(\mathrm{CH}_{3} \mathrm{OH}\) or $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$ e. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) or \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\) f. \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) or $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$

Short Answer

Expert verified
a. NH₃ is more soluble. b. CH₃OCH₃ is more soluble. c. CH₃CH₂OH is more soluble. d. CH₃OH is more soluble. e. (CH₃)₃CCH₂OH is more soluble. f. CH₃CO₂H is more soluble.

Step by step solution

01

Identify polar functional groups

Both molecules possess a nitrogen atom and have the capability to form hydrogen bonds.
02

Compare hydrogen bonding capabilities

\(\mathrm{CH}_{3} \mathrm{NH}_{2}\) has the additional \(\mathrm{CH}_{3}\) group which makes it less polar than \(\mathrm{NH}_{3}\). Therefore, \(\mathrm{NH}_{3}\) is more soluble in water. b. Comparing \(\mathrm{CH}_{3} \mathrm{CN}\) and \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\):
03

Identify polar functional groups

Both molecules possess polar functional groups: \(\mathrm{CH}_{3} \mathrm{CN}\) has a nitrile group and \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has an ether group.
04

Compare hydrogen bonding capabilities

\(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has an oxygen atom that allows for hydrogen bonding, while \(\mathrm{CH}_{3} \mathrm{CN}\) does not. Therefore, \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) is more soluble in water. c. Comparing \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (ethanol) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (propane):
05

Identify polar functional groups

Ethanol has a polar hydroxyl group while propane has no polar functional groups.
06

Compare hydrogen bonding capabilities

Ethanol can form hydrogen bonds with water, while propane cannot. Therefore, ethanol is more soluble in water. d. Comparing \(\mathrm{CH}_{3} \mathrm{OH}\) (methanol) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (ethanol):
07

Identify polar functional groups

Both molecules possess polar hydroxyl groups and have the capability to form hydrogen bonds.
08

Compare size and polarity

Methanol is smaller and less "nonpolar" compared to ethanol. Therefore, methanol is more soluble in water. e. Comparing \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) and \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{OH}\):
09

Identify polar functional groups

Both molecules possess polar hydroxyl groups and have the capability to form hydrogen bonds.
10

Compare size and polarity

The second molecule has a longer nonpolar hydrocarbon chain, which reduces its solubility in water. Therefore, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{OH}\) is more soluble in water. f. Comparing \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) and \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\):
11

Identify polar functional groups

\(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has a polar ether group, and \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) has a polar carboxylic acid group.
12

Compare hydrogen bonding capabilities

\(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) has a stronger hydrogen bonding capability due to its carboxylic acid group, while \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) has a weaker hydrogen bonding capability. Therefore, \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) is more soluble in water.

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