Solution Found!
Diethyl ether and butan-1-ol are isomers, and they have
Chapter 23, Problem 38SP(choose chapter or problem)
Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.
\(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{3}\) |
\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) |
diethyl ether, bp \(35\ ^{\circ}\mathrm{C}\) |
butan-1-ol, bp \(118\ ^{\circ}\mathrm{C}\) |
8.4 mL dissolves in 100 mL \(\mathrm{H}_{2} \mathrm{O}\) |
9.1 mL dissolves in 100 mL \(\mathrm{H}_{2} \mathrm{O}\) |
Equation Transcription:
Text Transcription:
CH_{3}CH_{2}-O-CH_{2}CH_{3}
35 o^C
H_{2}O
CH_{3}CH_{2}CH_{2}CH_{2}-OH
118 o^C
H_{2}O
Questions & Answers
QUESTION:
Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.
\(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{3}\) |
\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) |
diethyl ether, bp \(35\ ^{\circ}\mathrm{C}\) |
butan-1-ol, bp \(118\ ^{\circ}\mathrm{C}\) |
8.4 mL dissolves in 100 mL \(\mathrm{H}_{2} \mathrm{O}\) |
9.1 mL dissolves in 100 mL \(\mathrm{H}_{2} \mathrm{O}\) |
Equation Transcription:
Text Transcription:
CH_{3}CH_{2}-O-CH_{2}CH_{3}
35 o^C
H_{2}O
CH_{3}CH_{2}CH_{2}CH_{2}-OH
118 o^C
H_{2}O
ANSWER:
Solution:
Step 1
The boiling point of a molecule can be determined by of polarity. Diethyl ether, and 1-butanol both have similar size (number of electrons). Diethyl ether has two polar C-O bonds. 1-butanol also has two polar bonds (C-O and O-H), but the O-H bond is more polar than the C-O bond, making 1-butanol more polar