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How can you predict whether primary, secondary, and tertiary alcohol undergoes halogenation?

Answer 1

How else but by experiment............?

Chemistry is an experimental science; naturally, we try to interpret the experimental data using theoretical frameworks, but experimentation is the ultimate tool. We're not really sure what you want to accomplish in the reaction—replace the hydroxyl group with halogen, remove the hydroxyl group, and then hydrohalogenate the olefin, for example.

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Answer 2

Isaac Aronson

Primary alcohols can undergo halogenation, but the reaction requires harsh conditions and tends to yield low amounts of the desired product. Secondary and tertiary alcohols typically do not undergo halogenation under normal conditions due to steric hindrance and lack of reactivity at the carbon attached to the hydroxyl group.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.