Carbonyl Compounds

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Carbonyl Compounds
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IUPAC Names for Ketones

• Replace -e with -one. Indicate the position of
  the carbonyl with a number.
• Number the chain so that carbonyl carbon has the
  lowest number.
• For cyclic ketones the carbonyl carbon is
  assigned the number 1.

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Examples
3-methyl-2-butanone
3-bromocyclohexanone
4-hydroxy-3-methyl-2-butanone


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Naming Aldehydes

• IUPAC Replace -e with -al.
• The aldehyde carbon is number 1.
• 
  

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Examples
3-methylpentanal
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Common Names for Ketones

• Named as alkyl attachments to -CO.
• Use Greek letters instead of numbers.

methyl isopropyl ketone
a-bromoethyl isopropyl ketone
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Historical Common Names
acetophenone
acetone
benzophenone
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Aldehyde Common Names

• Use the common name of the acid.
• Drop -ic acid and add -aldehyde.
• 1 C formic acid, formaldehyde
• 2 Cs acetic acid, acetaldehyde
• 3 Cs propionic acid, propionaldehyde
• 4 Cs butyric acid, butyraldehyde.

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Name the following
2,4-dimethyl-3-hexanone
2-methylcycloheptanone
2-propanone
butanal
acetone
butyraldehyde
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IR Spectroscopy

• Very strong CO stretch around 1710 cm-1.
• Conjugation lowers frequency.
• Ring strain raises frequency.
• Additional C-H stretch for aldehyde two
  absorptions at 2710 cm-1 and 2810 cm-1.

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How can you tell the difference between the
following compounds by their IR spectra?
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Esters are higher frequency
Amides are lower frequency
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H NMR
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1H NMR Spectroscopy
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13C NMR Spectroscopy
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MS for 2-Butanone
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Provide the structure of the diethyl acetal of
butanal.
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Propose a sequence of steps to carry out the
following conversion.
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When the following compound is heated in the
prosence of an acid catalyst, a reaction occurs.
The product has the formula C6H11N. Provide the
structure of this product.
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When the following compound is heated in the
presence of an acid catalyst, a reaction occurs.
This product has the formula C9H16O2. Provide the
structure of this product.  
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Which of the following is also known as a Schiff
base? a) an imine b) a cyanohydrin c) a
hydrate d) sodium hydroxide e) an aldehyde
A