 Solution

ID: past-exam-of-the-chemistry-course-of-the-year-1-of-the-natural-sciences-course-of-the-university-of-cambridge/2021/paper-1/3/a/ii/solution

Iodomethane: faster, because iodide is a better leaving group and the C-I bond is more readily broken than C-Cl.
1-Chloropropane: slower than methyl chloride for SN2, because its ethyl substituent crowds backside approach and raises the substitution barrier. It is still a primary substrate, so SN2 remains plausible.
MeSNa: generally faster substitution with methanethiolate than methoxide in this protic solvent. Sulfur is more polarizable and its larger anion is less strongly hydrogen-bond-solvated, making it a better nucleophile here. This must not be inferred simply from basicity: methanethiolate is the weaker base.

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