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The Aldol Addition

How will you ...

Question

How will you convert ethanal into the following compounds ?

Butane - 1, 3 - diol

But - 2 - enal

But - 2 - enoic acid

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Solution

Part (a): Conversion of Ethanal to butane - 1,3 - diol
Ethanal undergoes Aldol condensation in presence of dilute Sodium hydroxide, leading to the formation of 3-hydroxy butanal.
$C H_{3} C H O D i l . N a O H - ----------- \to A l d o l c o n d e n s a t i o n C H_{3} - C H O H - C H_{2} - C H O$
$condensationDil.NaOHCH3−CHOH−CH2−CHOCH_3CHO\xrightarrow[Aldol\;condensation]{Dil.NaOH}CH_3-CHOH-CH_2-CH$
3-hydroxy butanal reacts with Sodium borohydride $(N a B H_{4})$ $NaBH_4)$ leading to the formation of Butan-1,3-diol.
$C H_{3} - C H O H - C H_{2} - C H O N a B H_{4} - ------ \to (R e d u c t i o n) C H_{3} - C H O H - C H_{2} - C H_{2} O H$
$CH3−CHOH−CH2−CHO→(Reduction)NaBH4CH3−CHOH−CH2−CH2OHCH_3-CHOH-CH_2-CHO\xrightarrow[(Reduction)]{NaBH_4}CH_3-CHOH-CH_2-CH_2O$

Part (b): Conversion of Ethanal to but-2-enal
Ethanal undergoes Aldol condensation in presence of dilute Sodium hydroxide, leading to the formation of 3-hydroxy butanal.
$C H_{3} C H O D i l . N a O H - ----------- \to A l d o l c o n d e n s a t i o n C H_{3} - C H O H - C H_{2} - C H O$
On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
$C H_{3} - C H O H - C H_{2} - C H O Δ - ---- \to (- H_{2} O) C H_{3} - C H = C H - C H O$

Part (c): Conversion of Ethanal into but-2-enoic acid
Ethanal undergoes Aldol condensation in presence of dilute Sodium hydroxide, leading to the formation of 3-hydroxy butanal.
$C H_{3} C H O D i l . N a O H - ----------- \to A l d o l c o n d e n s a t i o n C H_{3} - C H O H - C H_{2} - C H O$
On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
$C H_{3} - C H O H - C H_{2} - C H O Δ - --- \to - H_{2} O C H_{3} - C H = C H - C H O$
But-2-enal undergoes oxidation in presence of Tollens' reagent to form But-2-enoic acid.
$C H_{3} - C H = C H - C H O [A g N H_{3}]^{2 +} O H^{-} - --------- \to T o l l e n^{'} s r e a g e n t C H_{3} - C H = C H - C O O H$

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The Aldol Addition

Standard XII Chemistry

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