Question
Arrange ammonia, methylamine, dimethylamine, and trimethylamine in order of decreasing basicity in aqueous solution and explain the observed trend.
Solution — Step by Step
Spot the conceptual trap first, then give the clean answer. Read what is asked and identify the concept — in this case, amines. Note down the given data and the unknown.
Observed order in water: . The pure electronic argument ( of methyl should increase basicity steadily) predicts , but water adds a solvation penalty. The protonated form (ammonium cation) is stabilised by hydrogen bonding to water. More N-H bonds means more H-bond donors, so more stabilisation. Trimethylammonium has only one N-H and loses solvation stability. Net result: secondary amine wins in water. In the gas phase, the pure order holds.
Now we write the final answer in a single sentence so the examiner can find it at a glance. In board exams, bold or box the answer — it matters for marks.
Why This Works
This problem looks like a memory question but it is really a reasoning question. The key is to identify the physical or chemical principle at play and then apply it cleanly, without getting distracted by surface features. Students who only memorise facts get stuck on slight variations; students who reason from principles handle any variation.
Whenever you hit a chemistry question that mentions a trend or comparison, ask: ‘what property decides this?’ Then list the candidates — electronegativity, size, bond energy, polarity, resonance — and pick the one that varies in the question.
Alternative Method
A faster route to the same answer is to compare with a known benchmark. For instance, if you remember one clean example from class, you can often reason by analogy rather than rebuilding the theory from scratch. Toppers use this shortcut all the time during JEE Main, where every minute counts.
Common Mistake
Memorising the gas-phase order and applying it to aqueous solution. Always check the phase: JEE questions almost always mean ‘in aqueous solution’ unless specified.
Exam Connection
This kind of question is a reliable marks-scorer in CBSE board papers and JEE Main. Examiners reuse the underlying concept with small cosmetic changes — different numbers, a renamed compound, a twist in the wording. If you understand the reasoning here, you will recognise the pattern in any future variant. That is the difference between solving one question and solving a question type.
Teachers often say, “practise till the method becomes boring.” What they mean is: work through enough variations that the decision tree inside your head becomes automatic. By the time you sit the exam, your pen should know the first three steps before your brain consciously thinks about them.
Practice Extension
Try these follow-up variations on your own and see if your method still works:
- Change the starting quantity (e.g. 4.6 g becomes 9.2 g) and confirm that the final answer scales linearly.
- Swap the reagent for a close analogue (e.g. instead of ) and check which steps stay the same and which change.
- Flip the question — given the product, work backwards to find the starting amount. This reverse drill tests whether you really understand the stoichiometry, or whether you were just plugging into a memorised chain.
- Add an impurity (e.g. “the sample is only 80% pure”) and adjust the mole calculation. Purity questions are a classic twist in JEE Main.
In JEE Main, the cut-off between a 95 percentile and a 99 percentile is often just 3 to 4 questions of this exact difficulty. Practising these variations matters more than learning new topics during the last month of preparation.
Quick Recap
- Identify the concept before touching numbers.
- Write units on every line — they catch errors automatically.
- Reach the final answer in a single bold or boxed expression so the examiner sees it instantly.
- When stuck, ask: “what quantity is conserved here?” Conservation of mass, charge, and energy solve most chemistry problems.