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Q8.6(ii):
Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents. (ii) Tollens’ reagent

Solution :

Step 1: Chemical Identification of Reactants

The substrate is cyclohexanecarbaldehyde, which consists of a cyclohexane ring bonded to a formyl group ($-CHO$). The molecular formula is $C_7H_{12}O$.

The reagent is Tollens’ reagent, an ammoniacal silver nitrate solution containing the diamminesilver(I) complex ion, $[Ag(NH_3)_2]^+$. [Per the fundamental property of aldehydes as mild reducing agents].

Step 2: Mechanism of Oxidation

Tollens’ reagent acts as a selective oxidizing agent for aldehydes. It does not oxidize ketones or other functional groups under standard conditions. The aldehyde is oxidized to a carboxylate anion ($RCOO^-$) in the presence of the basic medium of the Tollens' reagent ($OH^-$ ions).

The chemical transformation follows the general reaction:

$R-CHO + 2[Ag(NH_3)_2]^+ + 3OH^- \rightarrow R-COO^- + 2Ag(s) + 4NH_3 + 2H_2O$

Step 3: Application to Cyclohexanecarbaldehyde

Substituting $R$ with the cyclohexyl group ($C_6H_{11}$):

$C_6H_{11}CHO + 2[Ag(NH_3)_2]^+ + 3OH^- \rightarrow C_6H_{11}COO^- + 2Ag(s) + 4NH_3 + 2H_2O$

The product formed is the cyclohexanecarboxylate ion. Upon subsequent acidification (standard workup), this yields cyclohexanecarboxylic acid ($C_6H_{11}COOH$). The formation of metallic silver ($Ag$) manifests as a "silver mirror" on the inner walls of the reaction vessel. [By the principle of Redox stoichiometry].

-CHO -COO⁻ Tollens' Reagent (Ag⁺/OH⁻)

Step 4: Summary of Reaction Observations

Component Role
Cyclohexanecarbaldehyde Reducing agent (oxidized to carboxylate)
$[Ag(NH_3)_2]^+$ Oxidizing agent (reduced to $Ag^0$)
Observable Product Silver Mirror (Precipitate of $Ag$)

Final Solution: The oxidation of cyclohexanecarbaldehyde with Tollens’ reagent yields cyclohexanecarboxylate ion (which yields cyclohexanecarboxylic acid upon acidification) and a silver mirror deposit ($2Ag$).


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