Answer: The reaction requires a phenolic substrate; haloalkanes lack the activating -OH group on an aromatic ring.
- A Haloalkanes generally cannot be mixed safely with chloroform and aqueous base together according to most researchers
- B The reaction requires a phenolic substrate; haloalkanes lack the activating -OH group on an aromatic ring
- C Haloalkanes are far too chemically reactive to survive the reaction conditions in the majority of cases studied
- D Haloalkanes fail to dissolve in the aqueous sodium hydroxide solution used as widely reported in standard practice
Correct answer: B. The reaction requires a phenolic substrate; haloalkanes lack the activating -OH group on an aromatic ring
Explanation: The Reimer-Tiemann reaction introduces a -CHO group ortho to the -OH in phenols using CHCl₃/NaOH via a dichlorocarbene intermediate. Haloalkanes do not have the aromatic ring with a phenolic -OH group needed to activate and direct the reaction.
SN2 proceeds in a single step with backside attack and inversion of configuration, while SN1 forms a planar carbocation intermediate first, leading to racemisation.
Concept context
Study carbon-halogen compounds: how they are made, how they react via SN1/SN2 and elimination, their stereochemistry, and their environmental impact.