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Question
How will you convert ethanal into the following compounds ?
Butane - 1, 3 - diol
But - 2 - enal
But - 2 - enoic acid
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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- CH3CHO→Aldol condensationDil.NaOHCH3−CHOH−CH2−CHOCH_3CHO\xrightarrow[Aldol\;condensation]{Dil.NaOH}CH_3-CHOH-CH_2-CH
- 3-hydroxy butanal reacts with Sodium borohydride(NaBH4)(NaBH4)(NaBH_4) leading to the formation of Butan-1,3-diol.
- CH3−CHOH−CH2−CHONaBH4−−−−−−−→(Reduction)CH3−CHOH−CH2−CH2OH
- 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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
- CH3−CHOH−CH2−CHOΔ−−−−−→(−H2O)CH3−CH=CH−CHO
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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
- CH3−CHOH−CH2−CHOΔ−−−−→−H2OCH3−CH=CH−CHO
- But-2-enal undergoes oxidation in presence of Tollens' reagent to form But-2-enoic acid.
- CH3−CH=CH−CHO[AgNH3]2+OH−−−−−−−−−−−→Tollen′sreagentCH3−CH=CH−COOH
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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- CH3CHO→Aldol condensationDil.NaOHCH3−CHOH−CH2−CHOCH_3CHO\xrightarrow[Aldol\;condensation]{Dil.NaOH}CH_3-CHOH-CH_2-CH
- 3-hydroxy butanal reacts with Sodium borohydride(NaBH4)(NaBH4)(NaBH_4) leading to the formation of Butan-1,3-diol.
- CH3−CHOH−CH2−CHONaBH4−−−−−−−→(Reduction)CH3−CHOH−CH2−CH2OH
- 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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
- CH3−CHOH−CH2−CHOΔ−−−−−→(−H2O)CH3−CH=CH−CHO
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.
- CH3CHODil.NaOH−−−−−−−−−−−−→AldolcondensationCH3−CHOH−CH2−CHO
- On heating, the 3-hydroxy butanal leads to the formation of But-2-enal with the elimination of water molecules.
- CH3−CHOH−CH2−CHOΔ−−−−→−H2OCH3−CH=CH−CHO
- But-2-enal undergoes oxidation in presence of Tollens' reagent to form But-2-enoic acid.
- CH3−CH=CH−CHO[AgNH3]2+OH−−−−−−−−−−−→Tollen′sreagentCH3−CH=CH−COOH
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