Try it on paper first. A hint, the key idea and the worked solution are here when you need them.
Bond enthalpies in : C-H in methane ; , H-Br , -Br ; , H-I , -I ; , H-Cl , -Cl . A free radical chain has two propagation steps: and . For each step the energy change is the bond enthalpy broken minus the bond enthalpy formed. Find the energy change of each step for bromine and the overall change for iodine. Then find the heat released when of methane, of molar mass , is converted to chloromethane by chlorine.
In free radical halogenation the share of a product is proportional to the number of hydrogen atoms times their reactivity. Bond enthalpies give the energy change of a step: bonds broken minus bonds formed. Hydrogen halides add to alkenes by Markovnikov's rule, and an alcohol with NaBr and sulphuric acid gives a bromoalkane.
Have you tried it?
Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Plan. Apply bonds broken minus bonds formed to each step.
Step 1. Bromine, step 1. .
Step 2. Bromine, step 2. .
Step 3. Iodine, overall. Step 1: . Step 2: . The sum is . The reaction takes in energy overall.
Step 4. Chlorine. Step 1: . Step 2: . The overall change is of methane.
Step 5. Heat released. , so is released.
Answer: and for bromine, overall for iodine, and released with chlorine.
Check. Iodination is uphill overall and its first step is uphill by . That is why iodine is not used for this reaction.
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