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Q8.7(v):
Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction. (v) Cyclohexanone

Solution :

Step 1: Structural Analysis of Cyclohexanone

The molecular structure of cyclohexanone is a six-membered cyclic ketone with a carbonyl group ($C=O$) located at the C1 position. To determine reactivity, we must identify the presence of $\alpha$-hydrogens.

  • The carbonyl carbon is C1.
  • The adjacent carbons (C2 and C6) are the $\alpha$-carbons.
  • Each $\alpha$-carbon is bonded to two hydrogen atoms.

Since cyclohexanone contains $\alpha$-hydrogens ($4$ in total), it is chemically capable of undergoing aldol condensation [Per the mechanism of enolate ion formation in the presence of dilute base]. It does not undergo the Cannizzaro reaction because that reaction is strictly reserved for aldehydes lacking $\alpha$-hydrogens [Per the definition of the Cannizzaro reaction involving hydride transfer in concentrated alkali].

Step 2: Aldol Condensation Mechanism

Cyclohexanone undergoes self-aldol condensation. In the presence of a dilute base (e.g., $NaOH$), one molecule of cyclohexanone forms an enolate at the $\alpha$-position, which then performs a nucleophilic attack on the carbonyl carbon of a second molecule.

O → O OH

The resulting $\beta$-hydroxy ketone is 2-(1-hydroxycyclohexyl)cyclohexan-1-one. Upon heating, this typically undergoes dehydration to form an $\alpha,\beta$-unsaturated ketone [Per the E1cB elimination mechanism].

Step 3: Comparative Summary Table

Reaction Type Capability Justification
Aldol Condensation Yes Presence of $\alpha$-hydrogens on C2 and C6 positions.
Cannizzaro Reaction No Requires absence of $\alpha$-hydrogens; ketone has four.

Step 4: Final Reaction Equations

Aldol Condensation Product: 2-(1-hydroxycyclohexyl)cyclohexan-1-one.
$2 \cdot C_6H_{10}O \xrightarrow{dil. NaOH} C_{12}H_{20}O_2$

Cannizzaro Reaction: Not applicable to cyclohexanone.

Final Solution: Cyclohexanone undergoes aldol condensation due to the presence of $\alpha$-hydrogens, resulting in the formation of 2-(1-hydroxycyclohexyl)cyclohexan-1-one; it does not undergo the Cannizzaro reaction.


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