Physical Properties and Hydrogen Bonding
Hydrogen bonding in alcohols and phenols increases boiling point and supports water solubility, especially for lower members.
In one line: O-H raises boiling point; long carbon chain lowers water friendship.
Practice This ConceptUnderstand it
- Alcohols and phenols have polar O-H bonds, so molecules can form intermolecular hydrogen bonds.
- This makes their boiling points higher than comparable hydrocarbons and ethers of similar molar mass.
- Lower alcohols are soluble in water because they can hydrogen-bond with water, but solubility decreases as the non-polar hydrocarbon chain becomes larger.
- Ethers can accept hydrogen bonds from water but cannot donate hydrogen bonds to each other because they lack an O-H bond.
Example
Rule to remember
Trend rule: stronger intermolecular hydrogen bonding gives higher boiling point; water solubility decreases as the alkyl chain length increases.
See it worked out
Follow the example line by line, then use the same method on new questions.
Worked example
- 1Compare water solubility of ethanol and hexan-1-ol.
- 2Both contain -OH, but hexan-1-ol has a much larger non-polar chain, so ethanol is more soluble.
Method you can reuse
Visual tip
A simple hydrogen-bond sketch between alcohol molecules or between alcohol and water is useful but not essential.
Check yourself
Answer the question in your head before opening the answer.
Try it yourself
Why does ethanol have a higher boiling point than dimethyl ether though both have the same molecular formula?
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Common wrong answer
Saying ethers are completely unable to hydrogen-bond is incorrect; ethers can accept hydrogen bonds from water but do not self-associate like alcohols.
Don't mix this up
Exam tip
Write it in the exam
Each point is worth about one mark. Write point 1 for a 1-mark question and keep adding points as the marks go up.
How CBSE asks it
- 1
Enough for 1 mark
Hydrogen bonding in alcohols and phenols increases boiling point and supports water solubility, especially for lower members.
- 2
Add for 2 marks
Example: Ethanol is much more soluble in water than pentanol because the ethyl group is small, while the pentyl group has a larger hydrophobic part.
- 3
Add for 3 marks
Alcohols and phenols have polar O-H bonds, so molecules can form intermolecular hydrogen bonds.
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