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Which pair of compounds will both produce a positive result with Tollens’ reagent?

1. Glucose and sucrose
2. Fructose and sucrose
3. Acetophenone and hexanal
4. Glucose and fructose

Correct answer: Glucose and fructose

Solution

Both glucose and fructose give a positive Tollens test. Glucose has a free aldehyde; fructose (a ketose) tautomerises to an aldose under the basic conditions and is also oxidised. Sucrose is non-reducing (no free anomeric OH).

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