Problem Solving Session: Aldehydes And Ketones - Reduction and Oxidation Examples

Introduction

  • Aldehydes and ketones are important classes of organic compounds
  • They both contain a carbonyl group (C=O)
  • In this problem-solving session, we will focus on reduction and oxidation reactions involving aldehydes and ketones

Reduction of Aldehydes

  • Aldehydes can be reduced to primary alcohols
  • The reduction reaction is typically carried out using reducing agents such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4)
  • Examples:
    • Reduction of formaldehyde: HCHO + NaBH4 -> CH2OH + NaOH + BH3
    • Reduction of propanal: CH3CH2CH=O + LiAlH4 -> CH3CH2CH2OH + LiAlO2

Oxidation of Aldehydes

  • Aldehydes can be oxidized to carboxylic acids
  • The oxidation reaction is typically carried out using oxidizing agents such as potassium permanganate (KMnO4) or chromic acid (H2CrO4)
  • Examples:
    • Oxidation of formaldehyde: HCHO + 2[O] -> HCOOH
    • Oxidation of propanal: CH3CH2CH=O + [O] -> CH3CH2COOH

Reduction of Ketones

  • Ketones can be reduced to secondary alcohols
  • The reduction reaction is similar to the reduction of aldehydes and uses the same types of reducing agents
  • Examples:
    • Reduction of acetone: (CH3)2C=O + NaBH4 -> (CH3)2CHOH + NaOH + BH3
    • Reduction of propanone: CH3COCH3 + LiAlH4 -> CH3CH(OH)CH3 + LiAlO2

Oxidation of Ketones

  • Ketones are generally not easily oxidized under normal conditions
  • However, in certain cases, ketones can be oxidized to esters using strong oxidizing agents
  • Examples:
    • Oxidation of acetone to methyl benzoate: (CH3)2C=O + O2 -> (CH3)2C(=O)OCH3
    • Oxidation of cyclohexanone to adipic acid: (CH2)5CO + [O] -> HOOC(CH2)4COOH

Summary

  • Aldehydes can be reduced to primary alcohols using reducing agents
  • Aldehydes can be oxidized to carboxylic acids using oxidizing agents
  • Ketones can be reduced to secondary alcohols using reducing agents
  • Ketones can be oxidized to esters in certain cases using strong oxidizing agents Thank you for attending this problem-solving session on aldehydes and ketones! If you have any questions, please feel free to ask.
  1. Reduction of Aldehydes
  • Aldehydes can be reduced to primary alcohols.
  • Reduction is typically carried out using reducing agents like NaBH4 or LiAlH4.
  • Example: Reduction of formaldehyde:
    • HCHO + NaBH4 -> CH2OH + NaOH + BH3
  • Example: Reduction of propanal:
    • CH3CH2CH=O + LiAlH4 -> CH3CH2CH2OH + LiAlO2
  1. Oxidation of Aldehydes
  • Aldehydes can be oxidized to carboxylic acids.
  • Oxidation is typically carried out using oxidizing agents like KMnO4 or H2CrO4.
  • Example: Oxidation of formaldehyde:
    • HCHO + 2[O] -> HCOOH
  • Example: Oxidation of propanal:
    • CH3CH2CH=O + [O] -> CH3CH2COOH
  1. Reduction of Ketones
  • Ketones can be reduced to secondary alcohols.
  • The reduction reaction is similar to that of aldehydes and uses reducing agents.
  • Example: Reduction of acetone:
    • (CH3)2C=O + NaBH4 -> (CH3)2CHOH + NaOH + BH3
  • Example: Reduction of propanone:
    • CH3COCH3 + LiAlH4 -> CH3CH(OH)CH3 + LiAlO2
  1. Oxidation of Ketones
  • Ketones are generally not easily oxidized under normal conditions.
  • However, in some cases, ketones can be oxidized to esters using strong oxidizing agents.
  • Example: Oxidation of acetone to methyl benzoate:
    • (CH3)2C=O + O2 -> (CH3)2C(=O)OCH3
  • Example: Oxidation of cyclohexanone to adipic acid:
    • (CH2)5CO + [O] -> HOOC(CH2)4COOH
  1. Summary: Reduction and Oxidation of Aldehydes and Ketones
  • Aldehydes can be reduced to primary alcohols using reducing agents like NaBH4 or LiAlH4.
  • Aldehydes can be oxidized to carboxylic acids using oxidizing agents like KMnO4 or H2CrO4.
  • Ketones can be reduced to secondary alcohols using reducing agents like NaBH4 or LiAlH4.
  • Ketones can be oxidized to esters in some cases using strong oxidizing agents.
  • Understanding and applying these reduction and oxidation reactions is important in organic chemistry.
  1. Example: Reduction of Benzaldehyde
  • Benzaldehyde (C6H5CHO) can be reduced to benzyl alcohol (C6H5CH2OH).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: C6H5CHO + 4H2 + NaBH4 -> C6H5CH2OH + NaBO2 + 4H2O
  • This reduction reaction is useful in the synthesis of various organic compounds.
  1. Example: Oxidation of Acetaldehyde
  • Acetaldehyde (CH3CHO) can be oxidized to acetic acid (CH3COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: CH3CHO + 2[O] -> CH3COOH
  • This oxidation reaction is important in the production of vinegar and other organic acids.
  1. Example: Reduction of Acetophenone
  • Acetophenone (C6H5C(O)CH3) can be reduced to 1-phenylethanol (C6H5CH2CH2OH).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: C6H5C(O)CH3 + 4H2 + NaBH4 -> C6H5CH2CH2OH + NaBO2 + 4H2O
  • This reduction reaction is useful in the synthesis of various pharmaceuticals and fragrances.
  1. Example: Oxidation of Acetone
  • Acetone ((CH3)2CO) can be oxidized to acetic acid (CH3COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: (CH3)2CO + [O] -> CH3COOH
  • Acetone oxidation is important in the industrial production of solvents, plastics, and other chemicals.
  1. Example: Oxidation of Cyclohexanone
  • Cyclohexanone (C6H10O) can be oxidized to adipic acid (HOOC(CH2)4COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: C6H10O + [O] -> HOOC(CH2)4COOH
  • Cyclohexanone oxidation is important in the production of nylon-6,6, a commonly used synthetic polymer.
  1. Reduction of Benzophenone
  • Benzophenone (C6H5C(O)C6H5) can be reduced to diphenylmethanol (C6H5CH(OH)C6H5).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: C6H5C(O)C6H5 + 4H2 + NaBH4 -> C6H5CH(OH)C6H5 + NaBO2 + 4H2O
  1. Oxidation of Formaldehyde
  • Formaldehyde (HCHO) can be oxidized to formic acid (HCOOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: HCHO + 2[O] -> HCOOH
  1. Reduction of Butanone
  • Butanone (C4H8O) can be reduced to 2-butanol (C4H10O).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: CH3COC2H5 + 2H2 + NaBH4 -> CH3CH(OH)C2H5 + NaBO2 + 2H2O
  1. Oxidation of Acetophenone
  • Acetophenone (C6H5C(O)CH3) can be oxidized to benzoic acid (C6H5COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: C6H5C(O)CH3 + 2[O] -> C6H5COOH + CH3COCH3
  1. Reduction of Propanal
  • Propanal (CH3CH2CHO) can be reduced to propanol (CH3CH2CH2OH).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: CH3CH2CHO + 2H2 + NaBH4 -> CH3CH2CH2OH + NaBO2 + 2H2O
  1. Oxidation of Acetone
  • Acetone ((CH3)2CO) can be oxidized to acetic acid (CH3COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: (CH3)2CO + [O] -> CH3COOH
  1. Reduction of Cyclohexanone
  • Cyclohexanone (C6H10O) can be reduced to cyclohexanol (C6H12O).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: C6H10O + 2H2 + NaBH4 -> C6H12O + NaBO2 + 2H2O
  1. Oxidation of Benzaldehyde
  • Benzaldehyde (C6H5CHO) can be oxidized to benzoic acid (C6H5COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: C6H5CHO + 2[O] -> C6H5COOH
  1. Reduction of Butanone
  • Butanone (C4H8O) can be reduced to 2-butanol (C4H10O).
  • The reaction is typically carried out using NaBH4 or LiAlH4.
  • Equation: (CH3)3COCH3 + 2H2 + NaBH4 -> (CH3)3CHOH + NaBO2 + 2H2O
  1. Oxidation of Propanal
  • Propanal (CH3CH2CHO) can be oxidized to propanoic acid (CH3CH2COOH).
  • The reaction is typically carried out using KMnO4 or H2CrO4.
  • Equation: CH3CH2CHO + [O] -> CH3CH2COOH