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Properties and mechanisms of carbonyl compounds

  • All carbonyls contain a polar C = O (O is deltanegative, C is deltapositive)

  • Resulting in polar molecules, dipole-dipole interaction

  • No hydrogen bonds

    • Lower boiling points than their alcohol counterparts

    • Higher boiling points than there alkane counterparts

  • Small carbonyls are water soluble as they can form hydrogen bonds with water

  • As chain length increases, solubility decreases, as the chain is non-polar and won’t be able to interact with the water and the longer it gets, the more of an effect it has on solubility

Chemical reactions

  • As the C = O is unsaturated, reactions tend to be additions

  • Nucleophiles are attracted to the deltapositive carbon of C = O

Reaction with HCN:

  • The C≡N in the final product (hydroxynitrile) is the nitrile group - useful in synthesis, extends carbon chain by 1

  • Most hydroxynitriles are optically active

  • HCN is made in situ. Start with NaCN/KCN plus dilute hydrochloric acid. As soon as HCN is formed, it reactions with the carbonyl

Reduction:

  • Reagents: NaBH4 (sodium tetrahydridoborate). Provides the H:- nucleophile

    • Mild reducing agent, only reduces carbonyls

  • Conditions: Warm, in water

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Properties and mechanisms of carbonyl compounds

  • All carbonyls contain a polar C = O (O is deltanegative, C is deltapositive)

  • Resulting in polar molecules, dipole-dipole interaction

  • No hydrogen bonds

    • Lower boiling points than their alcohol counterparts

    • Higher boiling points than there alkane counterparts

  • Small carbonyls are water soluble as they can form hydrogen bonds with water

  • As chain length increases, solubility decreases, as the chain is non-polar and won’t be able to interact with the water and the longer it gets, the more of an effect it has on solubility

Chemical reactions

  • As the C = O is unsaturated, reactions tend to be additions

  • Nucleophiles are attracted to the deltapositive carbon of C = O

Reaction with HCN:

  • The C≡N in the final product (hydroxynitrile) is the nitrile group - useful in synthesis, extends carbon chain by 1

  • Most hydroxynitriles are optically active

  • HCN is made in situ. Start with NaCN/KCN plus dilute hydrochloric acid. As soon as HCN is formed, it reactions with the carbonyl

Reduction:

  • Reagents: NaBH4 (sodium tetrahydridoborate). Provides the H:- nucleophile

    • Mild reducing agent, only reduces carbonyls

  • Conditions: Warm, in water

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