9. Write the following reactions (15 points)--(a) D-glucose with Fehling's--(b) N-acyl-2-deoxy-ẞ, D-galactosamine formation with acetic anhydride.--(c) maltose with silver hydroxide ammonia solution (-silver mirror reaction-)

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Reactions and Products:

(a) D-glucose with Fehling's solution:

D-glucose is a reducing sugar due to the presence of a free anomeric hydroxyl group. When
treated with Fehling's solution (a mixture of cupric sulfate and potassium sodium tartrate), it
undergoes an oxidation-reduction reaction:

Reaction:

2 Cu²⁺ (from Fehling's) + H₂O + R-CH(OH)₄ (D-glucose) → 2 Cu⁺ (red precipitate) +


R-CH(OH)₃-COOH (gluconic acid) + H⁺

Products:

● Red copper oxide precipitate (characteristic of positive Fehling's test)


● Gluconic acid (oxidized form of glucose)

(b) N-acyl-2-deoxy-β, D-galactosamine formation with acetic anhydride:

2-deoxy-β, D-galactosamine is a derivative of galactose where the hydroxyl group on carbon


2 is replaced by a hydrogen atom. N-acylation refers to the introduction of an acetyl group
(-CH₃CO) to the amine (-NH₂) group. In this case, acetic anhydride (Ac₂O) acts as the
acetylating agent:

Reaction:

H₂N-C(CH₂OH)₄-CH(OH)-CH₂OH + Ac₂O → CH₃-CO-NH-C(CH₂OH)₄-CH(OH)-CH₂OH +


AcOH

Products:

● N-acetyl-2-deoxy-β, D-galactosamine (acetylated derivative of galactosamine)


● Acetic acid (byproduct of the reaction)

(c) Maltose with silver hydroxide ammonia solution ("silver mirror reaction"):

Maltose is another reducing sugar that can react with silver hydroxide ammonia solution
(Tollens' reagent) in the silver mirror reaction. Similar to Fehling's test, this reaction involves
the oxidation of the sugar and the reduction of silver ions:
Reaction:

R-CH(OH)₄-CH(OH)-CH(OH)₄-CH₂OH (maltose) + 4 Ag⁺ (from Tollens') + NH₃ + H₂O →


R-CH(OH)₄-CH(OH)-CH(OH)₄-COOH (maltoic acid) + 4 Ag (shiny silver mirror) + NH₄⁺

Products:

● Shiny silver mirror formed on the reaction vessel wall


● Maltoic acid (oxidized form of maltose)
● Ammonium ions

Note:

These are simplified representations of the reactions. The actual mechanisms may involve
intermediate steps and additional side reactions.

I hope this explanation clarifies the details of each reaction and the expected products! Feel
free to ask if you have any further questions about carbohydrate chemistry, sugar reactivity,
or specific test principles like Fehling's or Tollens' tests.

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