Bromination of Acetone · CHM152 · Interactive Learning Guide
Acetone reacts with bromine (Br₂) in acid solution. Bromine is orange-brown; the product is colorless. You'll watch the color fade in a spectrophotometer and use the data to figure out how each ingredient affects the reaction speed.
The big question: write a rate law — rate = k[acetone]ⁿ[H⁺]ᵐ[Br₂]ᵖ — and find n, m, and p experimentally.
| Run | What changes | [Br₂]₀ (M) | [HCl]₀ (M) | [Acetone]₀ (M) |
|---|---|---|---|---|
| Run 1 Baseline | — | 2.0 × 10⁻³ | 0.20 | 0.80 |
| Run 2 | [HCl] doubled | 2.0 × 10⁻³ | 0.40 | 0.80 |
| Run 3 | [Acetone] doubled | 2.0 × 10⁻³ | 0.20 | 1.60 |
Br₂ is the only reagent you track by color. Acetone and HCl are always in large excess so their concentrations barely change during a run.
Work through each tab in order. The quiz tab unlocks the answer key when you submit.
Acetone reacts through a two-step mechanism. The slow step determines the rate — and Br₂ is not in it.
Acid (H⁺) pulls a hydrogen off acetone to form an enol. This is slow because a C–H bond breaks — that takes energy.
No Br₂ appears in this step. The rate of the whole reaction is set here, before Br₂ ever shows up.
The enol reacts instantly with Br₂. This step is so fast that it doesn't control the pace of the reaction.
[Br₂] vs time is a straight line (constant slope = −k'). It doesn't matter how much Br₂ you start with — the line goes down at the same rate.
All 3 runs have the same [Br₂]₀, so we can't directly prove zero order from a concentration comparison. Instead, the straight line itself is the proof.
If your plot of [Br₂] vs time is linear (R² > 0.98), the reaction is zero order in Br₂. That's the check.
The slow enolization step controls the clock. Br₂ just waits.
You can't weigh Br₂ as it disappears. But you can shine light through the solution: the more Br₂ present, the more orange color, the more light absorbed.
A is proportional to [Br₂]. Plot A vs [Br₂] for known standards → get a straight line → use it to convert every absorbance reading into a [Br₂] value during your runs.
Adjust the Br₂ concentration of each standard below. The graph updates live.
The rate law tells you how the speed of a reaction depends on concentration:
You don't know n, m, and p ahead of time — you measure them. By changing one ingredient at a time across runs and watching how the slope changes, you can solve for each exponent.
Acetone and HCl are in huge excess compared to Br₂. Even after Br₂ is completely consumed, [acetone] and [H⁺] have barely changed. So for a single run:
This makes the math much simpler: within each run, you're really just studying the [Br₂] dependence.
Because all 3 runs have the same [Br₂]₀, the slope of each [Br₂] vs time plot equals −k'. Comparing k' values between runs isolates the effect of one reactant at a time:
| Comparison | Formula | Tells you |
|---|---|---|
| Run 2 / Run 1 | k'₂/k'₁ = 2ᵐ | [H⁺] doubled → find m |
| Run 3 / Run 1 | k'₃/k'₁ = 2ⁿ | [acetone] doubled → find n |
If the ratio = 1, exponent = 0. If ratio ≈ 2, exponent = 1. If ratio ≈ 4, exponent = 2. Round to nearest integer.
Calculate k for each run and average them. Units are M⁻ⁿ⁻ᵐ s⁻¹ — but if n=m=1, units are M⁻¹ s⁻¹.
Total time: ~65 minutes. You'll do Part A (standard curve) and Part B (3 kinetics runs).
| Std | mL of 10⁻² M Br₂ | mL DI water | [Br₂] (M) |
|---|---|---|---|
| 1 | 0.50 | 4.50 | 1.0 × 10⁻³ |
| 2 | 1.00 | 4.00 | 2.0 × 10⁻³ |
| 3 | 1.50 | 3.50 | 3.0 × 10⁻³ |
| 4 | 2.00 | 3.00 | 4.0 × 10⁻³ |
| 5 | 2.50 | 2.50 | 5.0 × 10⁻³ |
Each run uses a 10.0 mL total volume. Prepare the mixture table volumes below. Mix acetone + HCl + water in one beaker; Br₂ in another. Add Br₂ last and start the timer.
| Run | mL 10⁻² M Br₂ | mL 4.0 M HCl | mL 4.0 M Acetone | mL DI Water |
|---|---|---|---|---|
| Run 1 | 2.0 | 1.0 | 1.0 | 6.0 |
| Run 2 | 2.0 | 2.0 | 1.0 | 5.0 |
| Run 3 | 2.0 | 1.0 | 2.0 | 5.0 |
Click Start to see a simulated Run 1. Absorbance should decline roughly linearly.
You'll convert absorbance readings to concentration, plot [Br₂] vs time, extract slopes, compute k', find n and m, then calculate k. ~45 minutes.
[Br₂] = (A − intercept) / slopeFor each run, make a new worksheet:
=(B2 - intercept)/slope — drag down for all rowsAll 3 lines should be parallel (nearly equal slopes) if Br₂ is zero order. The slopes differ only because [acetone] or [H⁺] changes between runs.
| Step | Calculation | Expected result |
|---|---|---|
| k'₁ | |slope of Run 1| | ~6 × 10⁻⁶ M/s |
| k'₂ | |slope of Run 2| | ~12 × 10⁻⁶ M/s |
| k'₃ | |slope of Run 3| | ~12 × 10⁻⁶ M/s |
| m | log(k'₂/k'₁) / log(2) | ≈ 1 |
| n | log(k'₃/k'₁) / log(2) | ≈ 1 |
| k | k'₁ / ([ace]₁ × [H⁺]₁) | ~3.75 × 10⁻⁵ M⁻¹s⁻¹ |
Calculate k from each run separately, then average. If one run gives a very different k, recheck your calculations before assuming it's experimental error.
Select one answer per question, then Submit. Instant feedback below each question.
1. Which step in the bromination mechanism controls the overall rate?
2. Why is the reaction zero order in Br₂?
3. A graph of [Br₂] vs time gives a perfectly straight line. What order is this?
4. In Run 2, [HCl] is doubled compared to Run 1. The slope becomes twice as steep. What is the order in H⁺?
5. You prepare Run 1 with 2.0 mL of 10⁻² M Br₂ in 10.0 mL total. What is [Br₂]₀?
6. If k' = 6.0 × 10⁻⁶ M/s, [acetone] = 0.80 M, and [H⁺] = 0.20 M, what is k?
7. What does Beer's Law allow you to do in this experiment?