Q.(a) Complete the following reaction:
CH3-CH2-CH2-CH2-O-CH2-CH3 + HI →
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🔒 Start your 14-day free trial to unlock the full solution →Concept understanding — Hydrogen Bonding
Hydrogen Bonding: From Intuition to Precision
Imagine you're holding two magnets. If you bring the north pole of one close to the south pole of another, they snap together. Now imagine a much weaker version of that — a tiny tug, not a full lock. That's the spirit of hydrogen bonding.
In chemistry, atoms in a molecule share electrons through covalent bonds. But electrons aren't shared equally in all cases. Some atoms are greedy — they pull the shared electrons closer to themselves. Oxygen, nitrogen, and fluorine are the biggest electron-hoarders. When one of these atoms bonds with hydrogen, the hydrogen ends up with a slight positive charge (because its electron has been pulled away), and the other atom gets a slight negative charge.
Now here's the key: that slightly positive hydrogen is attracted to any nearby slightly negative atom (like oxygen, nitrogen, or fluorine) on another molecule. This attraction is a hydrogen bond.
A hydrogen bond is not a true chemical bond like a covalent or ionic bond. It's an intermolecular force — a strong dipole-dipole attraction — but weaker than covalent bonds (about 1/10th to 1/20th the strength).
The Precise Definition
A hydrogen bond is an attractive interaction between a hydrogen atom covalently bonded to a highly electronegative atom (N, O, or F) and another electronegative atom (N, O, or F) that has a lone pair of electrons.
We can write it as:
X—H⋯Y
where X and Y are N, O, or F. The dotted line (⋯) represents the hydrogen bond. X—H is the donor (the molecule that provides the hydrogen), and Y is the acceptor (the molecule that provides the lone pair).
Why Only N, O, and F?
Three things make these three elements special:
- High electronegativity — They pull electrons hard, creating a large partial positive charge on hydrogen.
- Small size — The lone pair on Y is compact, allowing the hydrogen to get very close. Closer distance means stronger attraction.
- Lone pairs — They have unshared electron pairs that can act as the acceptor.
Chlorine is electronegative, but it's too large — the hydrogen can't get close enough for a strong bond. Carbon is not electronegative enough.
What Makes Hydrogen Bonding Special?
Unlike other dipole-dipole interactions, hydrogen bonds are directional and stronger. They're about 5–30 kJ/mol, compared to 0.5–2 kJ/mol for ordinary van der Waals forces. This strength has dramatic consequences.
Real-World Consequences
Water's high boiling point — Water (H2O) boils at 100∘C, while hydrogen sulfide (H2S) boils at −60∘C. Both are similar molecules, but water forms hydrogen bonds; H2S does not (sulfur is not electronegative enough). Those bonds must be broken to boil water, requiring much more energy.
Ice floats — In liquid water, molecules jostle and form temporary hydrogen bonds. When water freezes, the molecules arrange into a hexagonal lattice held open by hydrogen bonds. This structure is less dense than liquid water — hence ice floats. Without hydrogen bonding, ice would sink, and lakes would freeze from the bottom up, killing aquatic life.
DNA double helix — The two strands of DNA are held together by hydrogen bonds between base pairs (adenine-thymine and guanine-cytosine). These bonds are strong enough to keep the strands together, but weak enough to be unzipped during replication. …
Why this formula?
Hydrogen Bonding: Why It Happens — The Reasoning, Not Just the Rule
Hydrogen bonding is not a full covalent bond — it's a special type of intermolecular attraction. To understand why it occurs, we must look at the electronic structure of the atoms involved.
1. The Core Requirement: A "Naked" Proton
A hydrogen bond forms when a hydrogen atom is covalently bonded to a highly electronegative atom (like F, O, or N). Why?
- Electronegativity difference pulls the bonding electron pair strongly toward the electronegative atom.
- The hydrogen atom is left with almost no electron cloud — it becomes a partially positive proton (δ+).
Key idea: The hydrogen is now a small, dense positive charge — it can get very close to a lone pair on another electronegative atom.
2. The Electrostatic Attraction (The "Why")
The partially positive hydrogen (δ+) is attracted to a lone pair of electrons on another electronegative atom (the acceptor).
This is electrostatic — Coulomb's law governs it:
F=4πε01⋅r2q1q2
- q1 = partial positive charge on H
- q2 = partial negative charge on lone pair
- r = distance between them
Because the hydrogen is so small, r is very small → force is strong (stronger than van der Waals, weaker than covalent).
3. Why Only F, O, N?
Not all electronegative atoms work. The atom must have:
| Property | Why it matters |
|---|---|
| High electronegativity | Pulls electron density away from H, creating δ+ |
| Small atomic size | Allows close approach of the H to the lone pair |
| At least one lone pair | Provides the negative site for attraction |
F, O, and N satisfy all three. Cl is electronegative but too large — the H cannot get close enough for a strong bond.
4. The "Formula" for Hydrogen Bond Strength
There is no single formula for hydrogen bond energy, but the strength depends on:
EH-bond∝r2δ+⋅δ−
Where:
- δ+ = partial charge on H (depends on electronegativity of donor atom)
- δ− = partial charge on acceptor lone pair
- r = distance between H and acceptor atom
Typical strengths (for context):
- Covalent bond: ~400 kJ/mol
- Hydrogen bond: 10–40 kJ/mol
- van der Waals: ~1–5 kJ/mol
5. Directionality — The "Linear" Preference
Hydrogen bonds are directional: the strongest interaction occurs when the donor H–X bond and the acceptor lone pair are collinear (180° angle).
Why? Because:
- The positive charge on H is concentrated along the bond axis …
(a) HI cleaves an unsymmetrical ether by the iodide ion attacking the smaller, less hindered alkyl group in an SN2 step, giving an alcohol from the larger group and an alkyl iodide from the smaller one. (b) Even though propan-1-ol and butane have comparable molecular masses, only propanol's –OH group can hydrogen-bond, which is why it boils far higher than butane. …
(a) HI cleaves the unsymmetrical ether by SN2 attack of I⁻ on the smaller (ethyl) alkyl group, giving butan-1-ol and ethyl iodide. (b) Propan-1-ol boils higher than butane because it can hydrogen-bond while butane cannot.
(a) CH3-CH2-CH2-CH2-O-CH2-CH3 (an unsymmetrical ether, 1-ethoxybutane) + HI:
Ethers are cleaved by strong acids like HI via protonation of the ether oxygen followed by nucleophilic attack of I⁻ on one of the alkyl carbons.
Both alkyl groups here (butyl and ethyl) are primary, so cleavage proceeds by the SN2 mechanism, and the nucleophile (I⁻) attacks the less hindered (smaller) alkyl group preferentially — i.e., the ethyl carbon rather than the bulkier butyl carbon.
With one equivalent (limited/cold) HI:
CH3CH2CH2CH2-O-CH2CH3 + HI → CH3CH2CH2CH2-OH (butan-1-ol) + CH3CH2-I (iodoethane)
(With excess/hot HI, the alcohol formed would itself be further converted to the corresponding alkyl iodide: CH3CH2CH2CH2OH + HI → CH3CH2CH2CH2I + H2O.)
(b) Why propanol has a higher boiling point than butane: …
Showing the 12 most recent of 21 on this concept.
- CBSE 2026Set ANNUAL1 markQ.Alcohols are more soluble in water than hydrocarbons of comparable molecular masses. Why?
›Reveal solutionSolution
Solubility in water depends on the ability to form hydrogen bonds with water; alcohols have a polar -OH group that hydrogen-bonds with water, whereas hydrocarbons are non-polar and cannot.
Water is a highly polar, hydrogen-bonding solvent. A solute dissolves well in water when it can interact with water molecules through similarly strong intermolecular forces (like dissolves like).
- Alcohols contain a polar -OH group. The oxygen's lone pairs and the O-H hydrogen can both participate in hydrogen bonding with surrounding water molecules, allowing alcohol molecules to be effectively surrounded and stabilised by the solvent (solvation). This makes alcohols appreciably soluble in water, especially the shorter-chain ones. …
- CBSE 2026Set ANNUAL1 markQ.Write true or false: Intermolecular hydrogen bond is formed between two different molecules of the same or different compounds.
›Reveal solutionSolution
True. Intermolecular hydrogen bonding occurs between two distinct molecules, while intramolecular hydrogen bonding occurs within one molecule.
A hydrogen bond forms when a hydrogen atom, covalently bonded to a highly electronegative atom (like F, O, or N), is attracted to a lone pair on another electronegative atom. This attraction can occur:
- Intermolecularly: between the hydrogen of one molecule and the electronegative atom of a DIFFERENT molecule (which can be of the same compound, e.g., water-water hydrogen bonding, or a different compound, e.g., water-ethanol hydrogen bonding). …
- CBSE 2025Set ANNUAL1 markQ.Solubility of water in alcohol is due to ______ bond.
›Reveal solutionSolution
Water dissolves in alcohol because both form intermolecular hydrogen bonds through their -OH groups.
Both water (H-O-H) and alcohols (R-O-H) have a highly polar O-H bond, with oxygen able to act as a hydrogen-bond acceptor and the O-H hydrogen able to act as a hydrogen-bond donor. When water and alcohol are mixed, new O-H...O hydrogen bonds form between the water and alcohol molecules, similar in strength to the hydrogen bonds broken w …
- CBSE 2024Set 56/3/11 markMCQQ.For the following question, two statements are given – one labelled as Assertion (A) and the other labelled as Reason (R). Select the correct answer from the codes (A), (B), (C) and (D) as given below. (A) Both Assertion (A) and Reason (R) are true and Reason (R) is the correct explanation of the Assertion (A). (B) Both Assertion (A) and Reason (R) are true, but Reason (R) is not the correct explanation of the Assertion (A). (C) Assertion (A) is true, but Reason (R) is false. (D) Assertion (A) is false, but Reason (R) is true. Assertion (A) : The boiling point of ethanol is higher than that of dimethyl ether. Reason (R) : Ethanol molecules are associated through hydrogen bonding whereas in dimethyl ether, it is not possible.
›Reveal solutionSolution
The key idea is that hydrogen bonding between ethanol molecules creates stronger intermolecular forces than the dipole-dipole forces in dimethyl ether, raising ethanol’s boiling point. The Assertion is true, the Reason is true, and the Reason correctly explains the Assertion — so the answer is (A).
Let’s unpack this step by step.
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What the question is really asking
You have two organic compounds with the same molecular formula, CX2HX6O: ethanol (CHX3CHX2OH) and dimethyl ether (CHX3OCHX3). Despite having identical molar masses, their boiling points differ sharply — ethanol boils at 78.4∘C, dimethyl ether at −24.8∘C. The Assertion states this fact; the Reason claims the cause is hydrogen bonding in ethanol but not in ether. We need to check both statements and their logical link.
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Why boiling point depends on intermolecular forces
Boiling point is the temperature at which the vapour pressure of a liquid equals atmospheric pressure. To boil, molecules must overcome the attractive forces holding them together in the liquid phase. Stronger intermolecular forces → more energy needed → higher boiling point. The three main types (in increasing strength) are: London dispersion forces (present in all molecules), dipole-dipole interactions (in polar molecules), and hydrogen bonding (a special, very strong dipole-dipole interaction involving H bonded to N, O, or F).
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Hydrogen bonding in ethanol — the critical difference
In ethanol, the —OH group has a hydrogen atom covalently bonded to a highly electronegative oxygen. This creates a large partial positive charge on the H and a large partial negative charge on the O. The H of one ethanol molecule is strongly attracted to the O of another, forming a hydrogen bond. These bonds link ethanol molecules into extended networks, so you need a lot of thermal energy to break them apart and vaporise the liquid.
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Why dimethyl ether cannot hydrogen-bond
Dimethyl ether has an oxygen atom, but every hydrogen is bonded to carbon — not to oxygen. The C–H bond is not polar enough to create the strong partial positive charge needed for hydrogen bonding. The only intermolecular forces in dimethyl ether are weaker dipole-dipole interactions (from the C–O–C dipole) and London forces. That’s why it boils at a much lower temperature. …
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- CBSE 2024Set ANNUAL1 markMCQQ.The reason for high boiling points of alcohols as compared to isomeric ethers is :(a) Solubility of alcohols in water(b) High reactivity(c) Association of molecules due to hydrogen-bonding(d) van der Waals forces
›Reveal solutionSolution
Alcohols have much higher boiling points than isomeric ethers because alcohol molecules are held together by intermolecular hydrogen bonding, while ether molecules are not.
An alcohol (R-OH) has a polar O-H bond, and the hydrogen (attached to the highly electronegative oxygen) can form a hydrogen bond with the lone pair of oxygen on a neighbouring alcohol molecule. This causes alcohol molecules to associate into chains/clusters through extensive intermolecular hydrogen bonding.
An ether (R-O-R'), though isomeric in molecular formula and having a similar dipole moment, has no O-H bond, so its molecules cannot hydrogen-bond to each other (only weaker dipole-dipole and van der Waals forces act between ether molecules).
…
- CBSE 2024Set ANNUAL1 markMCQQ.Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of dimethyl ether, due to the presence of –(a) H-bonding in dimethyl ether(b) H-bonding in ethanol(c) CH3CH2 group of ethanol(d) CH3 group of dimethyl ether
›Reveal solutionSolution
Ethanol's -OH group lets it hydrogen-bond with other ethanol molecules; dimethyl ether has no O-H bond and so cannot hydrogen-bond at all.
Ethanol (CH3CH2OH) has an −OH group, allowing intermolecular hydrogen bonding between its molecules — a strong dipole-dipole interaction that raises the boiling point significantly. Dimethyl ether (CH3−O−CH3) has its oxygen bonded to two carbon atoms, with no O–H bond at all, so it cannot hydrogen-bond (option a is therefore wrong — dimethyl ether has no H-bonding). Its inter …
- CBSE 2024Set ANNUAL1 markMCQQ.In which of the following is hydrogen bond not formed?(a) CH3COOH(b) NH3(c) C2H5OH(d) CH3COCH3
›Reveal solutionSolution
Acetone lacks an O–H/N–H/F–H bond, so it cannot form (self-associating) hydrogen bonds, unlike the other three.
- CH3COOH (acetic acid): has O–H → forms strong hydrogen bonds (even dimerizes).
- NH3: has N–H → forms hydrogen bonds.
- C2H5OH (ethanol): has O–H → forms hydrogen bonds. …
- CBSE 2024Set sz1 markMCQQ.Select the correct one: In which of the following compounds does hydrogen bond occur?(a) SiH4(b) LiH(c) HI(d) NH3
›Reveal solutionSolution
Hydrogen bonding occurs in NH3 because nitrogen is small and electronegative enough to polarize the N-H bond strongly, unlike Si in SiH4, Li in LiH, or I in HI.
A hydrogen bond forms when a hydrogen atom, covalently bonded to a small and highly electronegative atom (N, O, or F), is attracted to a lone pair on a similar electronegative atom of a neighbouring molecule.
Checking each option: SiH4 -- silicon has low electronegativity (comparable to hydrogen), so Si-H bonds are not polar enough. LiH -- this is an ionic hydride (Li+ H-), not a case of hydrogen bonding between molecules. HI -- although iodine is electronegative, it is too large and its electronegativity too low for the H-I bond to support hydrogen bonding (HI is in fact one of the weakest hydrogen halide acids in this regard). NH3 -- nitrogen is small and sufficiently electronegative, so the N-H bond is polar en …
- CBSE 2023Set ANNUAL1 markMCQQ.Alcohol boils at higher temperature than the corresponding hydrocarbon due to(a) intermolecular hydrogen bond(b) intra molecular hydrogen bond(c) van der waal's force of attraction(d) dipole-dipole interaction
›Reveal solutionSolution
The –OH group lets alcohol molecules hydrogen-bond to one another, an attraction hydrocarbons of similar mass simply cannot form.
Alcohol molecules associate with each other through intermolecular hydrogen bonding, since the O–H bond is highly polar (O is electronegative) and each molecule has both an H-bond donor (O–H) and acceptor (lone pairs on O). Considerable extra thermal energy is required to break these hydrogen bonds before the molecules can escape into the vapour ph …
- CBSE 2022Set ANNUAL1 markMCQQ.Alcohol are soluble in water because -(a) they have higher molecular weight than water.(b) they form Hydrogen Bond with water.(c) they displace water.(d) None of these.
›Reveal solutionSolution
Alcohols dissolve in water because their -OH group can hydrogen-bond with water molecules.
An alcohol molecule, R-OH, carries a polar -OH group in which the O-H bond is highly polarised. This -OH group can form hydrogen bonds with the -OH of water molecules (both as a hydrogen-bond donor and acceptor), just as water molecules hydrogen-bond with each other. This intermolecular hydrogen bonding lets the alcohol molecules mix intimately with water, so lower alcohols (methanol, ethanol, propanol) are miscible with water in all proportions. As the hydrocarbon (R) part of the alcohol becomes larger, the non-polar part dominates, hydrogen bonding contribution becomes relatively less significant, and solubility in w …
- CBSE 2022Set TERM21 markQ.Solubility of alcohols in water is due to their ability to form ................. bonds with water molecules.
›Reveal solutionSolution
Alcohols dissolve in water because the -OH group forms hydrogen bonds with water molecules.
The -OH group of an alcohol is polar: the oxygen carries a partial negative charge and the H a partial positive charge. Water molecules are similarly polar. When an alcohol is mixed with water, the O-H of the alcohol can hydrogen-bond with the O of water (and vice versa), pulling alcohol molecules into solution.
…
- CBSE 2022Set ANNUAL1 markQ.Why is H2O a liquid and H2S a gas?
›Reveal solutionSolution
Oxygen's small size and high electronegativity allow water molecules to hydrogen-bond strongly with each other, raising its boiling point well above room temperature; sulfur's much lower electronegativity and larger size mean H₂S cannot hydrogen-bond significantly, so only weak van der Waals forces hold its molecules together, keeping it a gas at room temperature.
The role of hydrogen bonding
A hydrogen bond forms when a hydrogen atom bonded to a highly electronegative, small atom (F, O, N) is attracted to a lone pair on a similarly electronegative atom in a neighbouring molecule. Its strength depends strongly on the electronegativity and size of that atom.
Comparing O and S
- Oxygen: electronegativity ≈3.44 (Pauling scale), small atomic radius. The O−H bond in water is highly polar, and oxygen's small size lets neighbouring molecules approach closely enough for a strong hydrogen bond. Each water molecule can form up to 4 hydrogen bonds (2 as donor via its 2 H atoms, 2 as acceptor via its 2 lone pairs), building an extensive 3D hydrogen-bonded network that requires substantial thermal energy to break — giving water its unusually high boiling point (100∘C) for such a small molecule. …
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