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Aldehydes and Ketones




    Chapter 13
1. Structure

   The carbonyl group is a double bond between oxygen and
    carbon.
   Carbonyl compounds include:
       Aldehydes: at least one hydrogen bonded to the carbonyl carbon




       Ketones: no hydrogens bonded to the carbonyl carbon.




       carboxylic acids and amides. [Tune in NEXT chapter…]
1. Properties

   The carbonyl group is polar.




   Intermolecular forces in carbonyl compounds are
       stronger than in alkanes (nonpolar) or ethers (only slightly polar).
       weaker than in alcohols, which are polar and can hydrogen bond.
1. Boiling points

   Structure         Name       Molar mass   Boiling point
CH3CH2CH2CH3       butane          58          -0.5 oC
CH3-O-CH2CH3    methoxyethane      60           7.0 oC
CH3CH2CH2-OH      1-propanol       60         97.2 oC
         O
         ||        propanal        58           49 oC
 CH3CH2-C-H
      O
      ||          propanone        58           56 oC
  CH3-C-CH3
1. Solubility

   There is no hydrogen bonding between two carbonyl
    groups.
1. Solubility

   Aldehydes and ketones can hydrogen bond with water.




       Aldehydes and ketones with five or fewer carbon atoms are fairly
        soluble in water.
       Large aldehydes and ketones dissolve only in nonpolar solvents.
1. Solubility in water—general guidelines


   Molecules with polar groups tend to be more soluble in
    water.
   Molecules that can hydrogen bond with water are more
    soluble than those than cannot.
   Increasing the number of polar groups on a molecule
    increases its water solubility.
   Increasing the number of possibilities for hydrogen bonding
    increases solubility in water.
   Increasing the molar mass of a molecule decreases its
    water solubility.
2. Nomenclature


   Naming aldehydes
       The parent compound is named for the longest continuous chain
        containing the carbonyl group.

       The final –e of the parent alkane is replaced with –al.

       The chain is numbered beginning at the carbonyl carbon.

       Substituents are named and numbered as usual.

       The aldehyde is always carbon 1, so no number is used for the
        carbonyl group.
2. Nomenclature

   The simplest aldehydes




             methanal                         ethanal


   Draw structures for

                                                        pencast
       7,8-dibromooctanal

       trans-2-hexenal (component of olive oil)
2. Nomenclature

   Name the following compounds.




                              pencast
2. Nomenclature


   Ketones
       The rules are analogous to the rules for aldehydes.

       The –e ending of the parent alkane is changed to –one.

       The location of the carbonyl is indicated with a number. [This
        number is never 1- because that would be an aldehyde!]

       The longest carbon chain is numbered to give the carbonyl the
        lowest possible number.
2. Nomenclature

   The simplest ketones need no number for the carbonyl.
    (Why?)



                       propanone      butanone
   Draw structures for the following compounds.

       2-fluorocyclohexanone

       3-chloro-2-pentanone
                                           pencast
2. Nomenclature

   Name the following compounds.




                             pencast
3. Important aldehydes and ketones

   What is the relationship between embalming fluid and
    methanol poisoning?

   What is the I.U.P.A.C. name of the following component of
    lemongrass?




                                                      pencast
3. Important aldehydes and ketones

   What is the I.U.P.A.C. name for cinnamaldehyde?




                                                                   pencast




   Chanel No. 5 became famous for containing synthetic
    aldehydes “in copious quantities”.*

      *Perfume Shrine
                        Follow the link for a fun description of
                        properties of aldehydes and ketones.
3. Important aldehydes and ketones

   Aldehydes in perfumery
       heptanal: naturally occuring in clary sage and possessing a herbal
        green odour

       octanal: orange-like

       nonanal: smelling of roses

       decanal: powerfully evocative of orange rind

       citral (a more complicated 10-carbon aldehyde): odor of lemons

       undecanal: naturally present in coriander leaf oil

       unsaturated undecen-1-al

       lauryl aldehyde (12 carbons): evocative of lilacs or violets
4. Reactions--oxidation

   Preparation is usually by oxidation of an alcohol.
       Aldehydes are produced from primary alcohols.




       Ketones are produced from secondary alcohols.




       Tertiary alcohols don’t undergo oxidation (no –H to lose).
4. Reactions--oxidation

   Oxidation of aldehydes and ketones
       Aldehydes can be oxidized to carboxylic acids.




                    loss of a bond to H, gain of a bond to O

       Ketones can’t be oxidized further.


                                             N.R. (no –H to lose)
4. Reactions--oxidation

   Tollen’s test is used to distinguish between aldehydes and
    ketones based on their ability to be oxidized.
       When one substance is oxidized, another must be reduced.


                + Ag(NH3)2+                          + Ago
                Tollen’s reagent                   elemental silver




       If an aldehyde is present, a “silver mirror” forms on the inside of the
        glass container.
       If a ketone is present, there is no reaction because it won’t undergo
        oxidation.
4. Reactions--oxidation

   The same process used in Tollen’s test used to be used to
    produce silvered mirrors.

   This is an article published in 1911 describing the process, if
    you are interested!

   Go here to see a 2-liter flask turned into a mirror.

   For EXTRA CREDIT, explain what precautions need to be
    taken when the Tollen’s test is carried out. You’ll have to
    watch the video. Post your answer in the Module 4 Journal
    Answers journal with the tag Tollen.
4. Reactions--oxidation

   Draw the structure of the following compounds and their
    oxidation products.

       2-methyl-2-propanol



       2-nonanol


                                      pencast
       1-decanol
4. Reactions--oxidation

   What reaction will pentanal undergo, if any, with Tollen’s
    reagent?




                     + Ag(NH3)2+                         + Ago

                                   pencast
4. Reactions--oxidation

   Benedict’s test is used to distinguish between reducing
    and non-reducing sugars.
       A reducing sugar can be oxidized.
       The substance reduced is Cu+2.




                         + Cu+2             + Cu2O
4. Reactions—blast from the past

   Can you remember Chapter 12?
       Preparation of alcohols by hydrogenation of aldehydes and ketones
        (slide 19)
4. Reactions--reduction

   Hydrogenation is a reduction reaction.
       More bonds to hydrogen, fewer bonds to oxygen


   Reduction of an aldehyde or ketone requires a Ni, Pt, or Pd
    catalyst. [sound familiar?]

       Reduction of an aldehyde produces a primary alcohol.
       Reduction of a ketone produces a secondary alcohol.
4. Reactions--reduction

   What is the product of reduction of

       1-chloropropanone?




                                          pencast
       2-methylpropanal?
4. Reactions--addition

   Take the time machine back to Chapter 11 now.
       Alkenes undergo addition reactions:
           Hydrogenation (addition of H2)
           Halogenation (addition of X2)
           Hydration (addition of H2O)
           Hydrohalogenation (addition of HX)
   General addition reaction
4. Reactions--addition

   Addition of an alcohol to an aldehyde:


                                    H+




   The product is called a hemiacetal (-OH and –OR attached
    to the same carbon).
       Hemiacetals are very reactive.
       They react with an additional alcohol molecule, losing –OH and
        adding another –OR.
4. Reactions--addition

   The final product is an acetal (2 –OR groups attached to
    one carbon).




                            hemiacetal             acetal
4. Reactions--addition

   Ketones undergo analogous addition reactions with
    alcohols.
       The initial product is a reactive hemiketal (two –R groups, one –OH,
        and one –OR).
       An additional –OR group is added to the hemiketal to produce a
        ketal.




                                  hemiketal                  ketal
4. Reactions--addition
4. Reactions

   Hemiacetal, acetal, hemiketal, or ketal?
4. Reactions

   Monosaccharide addition reactions


                                         alcohol
                6



                    5   ]
            4



                        2
                            1
                                ]           aldehyde



                    3




                                    -glucose
                                    D
4. Reactions

   Monosaccharide addition reactions


                                                 Hemiacetal:
                                                  one –H
                                                  one –OH
                            5
                                                  one –OR
                                                  one -R
                       4                 1



                                3    2




   The cyclic form is more stable than the linear form and no
    further oxidation takes place in this case.
4. Reactions: keto-enol tautomers

   Tautomers differ from each other in the placement of one
    hydrogen and one double bond.




            Keto form                      Enol form
             (ketone)                  (alcohol + alkene)

   The two forms exist in an equilibrium mixture, mostly in the
    keto form, which is more stable.
4. Reactions: keto-enol tautomers

   Draw the keto and enol forms of

       propanone.




                                      pencast
       propanal.
4. Reactions: aldol condensation

   In an aldol condensation, aldehydes or ketones react to
    make a larger molecule by forming a new carbon-carbon
    bond between two molecules.




                +
                             OH- or
                             enzyme
4. Reactions: aldol condensation

   Write an equation for the aldol condensation of two
    molecules of propanal.




                             pencast

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13 aldehydes-and-ketones

  • 2. 1. Structure  The carbonyl group is a double bond between oxygen and carbon.  Carbonyl compounds include:  Aldehydes: at least one hydrogen bonded to the carbonyl carbon  Ketones: no hydrogens bonded to the carbonyl carbon.  carboxylic acids and amides. [Tune in NEXT chapter…]
  • 3. 1. Properties  The carbonyl group is polar.  Intermolecular forces in carbonyl compounds are  stronger than in alkanes (nonpolar) or ethers (only slightly polar).  weaker than in alcohols, which are polar and can hydrogen bond.
  • 4. 1. Boiling points Structure Name Molar mass Boiling point CH3CH2CH2CH3 butane 58 -0.5 oC CH3-O-CH2CH3 methoxyethane 60 7.0 oC CH3CH2CH2-OH 1-propanol 60 97.2 oC O || propanal 58 49 oC CH3CH2-C-H O || propanone 58 56 oC CH3-C-CH3
  • 5. 1. Solubility  There is no hydrogen bonding between two carbonyl groups.
  • 6. 1. Solubility  Aldehydes and ketones can hydrogen bond with water.  Aldehydes and ketones with five or fewer carbon atoms are fairly soluble in water.  Large aldehydes and ketones dissolve only in nonpolar solvents.
  • 7. 1. Solubility in water—general guidelines  Molecules with polar groups tend to be more soluble in water.  Molecules that can hydrogen bond with water are more soluble than those than cannot.  Increasing the number of polar groups on a molecule increases its water solubility.  Increasing the number of possibilities for hydrogen bonding increases solubility in water.  Increasing the molar mass of a molecule decreases its water solubility.
  • 8. 2. Nomenclature  Naming aldehydes  The parent compound is named for the longest continuous chain containing the carbonyl group.  The final –e of the parent alkane is replaced with –al.  The chain is numbered beginning at the carbonyl carbon.  Substituents are named and numbered as usual.  The aldehyde is always carbon 1, so no number is used for the carbonyl group.
  • 9. 2. Nomenclature  The simplest aldehydes methanal ethanal  Draw structures for pencast  7,8-dibromooctanal  trans-2-hexenal (component of olive oil)
  • 10. 2. Nomenclature  Name the following compounds. pencast
  • 11. 2. Nomenclature  Ketones  The rules are analogous to the rules for aldehydes.  The –e ending of the parent alkane is changed to –one.  The location of the carbonyl is indicated with a number. [This number is never 1- because that would be an aldehyde!]  The longest carbon chain is numbered to give the carbonyl the lowest possible number.
  • 12. 2. Nomenclature  The simplest ketones need no number for the carbonyl. (Why?) propanone butanone  Draw structures for the following compounds.  2-fluorocyclohexanone  3-chloro-2-pentanone pencast
  • 13. 2. Nomenclature  Name the following compounds. pencast
  • 14. 3. Important aldehydes and ketones  What is the relationship between embalming fluid and methanol poisoning?  What is the I.U.P.A.C. name of the following component of lemongrass? pencast
  • 15. 3. Important aldehydes and ketones  What is the I.U.P.A.C. name for cinnamaldehyde? pencast  Chanel No. 5 became famous for containing synthetic aldehydes “in copious quantities”.* *Perfume Shrine Follow the link for a fun description of properties of aldehydes and ketones.
  • 16. 3. Important aldehydes and ketones  Aldehydes in perfumery  heptanal: naturally occuring in clary sage and possessing a herbal green odour  octanal: orange-like  nonanal: smelling of roses  decanal: powerfully evocative of orange rind  citral (a more complicated 10-carbon aldehyde): odor of lemons  undecanal: naturally present in coriander leaf oil  unsaturated undecen-1-al  lauryl aldehyde (12 carbons): evocative of lilacs or violets
  • 17. 4. Reactions--oxidation  Preparation is usually by oxidation of an alcohol.  Aldehydes are produced from primary alcohols.  Ketones are produced from secondary alcohols.  Tertiary alcohols don’t undergo oxidation (no –H to lose).
  • 18. 4. Reactions--oxidation  Oxidation of aldehydes and ketones  Aldehydes can be oxidized to carboxylic acids. loss of a bond to H, gain of a bond to O  Ketones can’t be oxidized further. N.R. (no –H to lose)
  • 19. 4. Reactions--oxidation  Tollen’s test is used to distinguish between aldehydes and ketones based on their ability to be oxidized.  When one substance is oxidized, another must be reduced. + Ag(NH3)2+  + Ago Tollen’s reagent elemental silver  If an aldehyde is present, a “silver mirror” forms on the inside of the glass container.  If a ketone is present, there is no reaction because it won’t undergo oxidation.
  • 20. 4. Reactions--oxidation  The same process used in Tollen’s test used to be used to produce silvered mirrors.  This is an article published in 1911 describing the process, if you are interested!  Go here to see a 2-liter flask turned into a mirror.  For EXTRA CREDIT, explain what precautions need to be taken when the Tollen’s test is carried out. You’ll have to watch the video. Post your answer in the Module 4 Journal Answers journal with the tag Tollen.
  • 21. 4. Reactions--oxidation  Draw the structure of the following compounds and their oxidation products.  2-methyl-2-propanol  2-nonanol pencast  1-decanol
  • 22. 4. Reactions--oxidation  What reaction will pentanal undergo, if any, with Tollen’s reagent? + Ag(NH3)2+  + Ago pencast
  • 23. 4. Reactions--oxidation  Benedict’s test is used to distinguish between reducing and non-reducing sugars.  A reducing sugar can be oxidized.  The substance reduced is Cu+2. + Cu+2  + Cu2O
  • 24. 4. Reactions—blast from the past  Can you remember Chapter 12?  Preparation of alcohols by hydrogenation of aldehydes and ketones (slide 19)
  • 25. 4. Reactions--reduction  Hydrogenation is a reduction reaction.  More bonds to hydrogen, fewer bonds to oxygen  Reduction of an aldehyde or ketone requires a Ni, Pt, or Pd catalyst. [sound familiar?]  Reduction of an aldehyde produces a primary alcohol.  Reduction of a ketone produces a secondary alcohol.
  • 26. 4. Reactions--reduction  What is the product of reduction of  1-chloropropanone? pencast  2-methylpropanal?
  • 27. 4. Reactions--addition  Take the time machine back to Chapter 11 now.  Alkenes undergo addition reactions:  Hydrogenation (addition of H2)  Halogenation (addition of X2)  Hydration (addition of H2O)  Hydrohalogenation (addition of HX)  General addition reaction
  • 28. 4. Reactions--addition  Addition of an alcohol to an aldehyde: H+  The product is called a hemiacetal (-OH and –OR attached to the same carbon).  Hemiacetals are very reactive.  They react with an additional alcohol molecule, losing –OH and adding another –OR.
  • 29. 4. Reactions--addition  The final product is an acetal (2 –OR groups attached to one carbon). hemiacetal acetal
  • 30. 4. Reactions--addition  Ketones undergo analogous addition reactions with alcohols.  The initial product is a reactive hemiketal (two –R groups, one –OH, and one –OR).  An additional –OR group is added to the hemiketal to produce a ketal. hemiketal ketal
  • 32. 4. Reactions  Hemiacetal, acetal, hemiketal, or ketal?
  • 33. 4. Reactions  Monosaccharide addition reactions alcohol 6 5 ] 4 2 1 ] aldehyde 3 -glucose D
  • 34. 4. Reactions  Monosaccharide addition reactions Hemiacetal: one –H one –OH 5 one –OR one -R 4 1 3 2  The cyclic form is more stable than the linear form and no further oxidation takes place in this case.
  • 35. 4. Reactions: keto-enol tautomers  Tautomers differ from each other in the placement of one hydrogen and one double bond. Keto form Enol form (ketone) (alcohol + alkene)  The two forms exist in an equilibrium mixture, mostly in the keto form, which is more stable.
  • 36. 4. Reactions: keto-enol tautomers  Draw the keto and enol forms of  propanone. pencast  propanal.
  • 37. 4. Reactions: aldol condensation  In an aldol condensation, aldehydes or ketones react to make a larger molecule by forming a new carbon-carbon bond between two molecules. + OH- or enzyme
  • 38. 4. Reactions: aldol condensation  Write an equation for the aldol condensation of two molecules of propanal. pencast

Editor's Notes

  1. Note that the alcohol has a dramatically higher boiling point because of its ability to hydrogen-bond with itself. Although the ketone on this slide has a higher boiling point than the aldehyde, this isn’t consistent. Aldehydes and ketones of the same molecular weight will always have similar boiling points, but it’s not possible to predict whether the aldehyde or the ketone will have the higher boiling point.Aldehydes and ketones can’t hydrogen bond with themselves because they lack a hydrogen bonded to the double-bonded oxygen. This is why they have lower boiling points than alcohols. Ethers are less polar than aldehydes and ketones because the oxygen atom is more “hidden” between two alkyl chains. Hence, their boiling points are much lower than aldehydes and ketones and only slightly higher than boiling points for comparable alkanes.
  2. There is one-way hydrogen bonding between aldehydes and ketones, and water. A partially positive hydrogen from water can be attracted to an unshared pair of electrons on a carbonyl oxygen. But aldehydes and ketones have no hydrogens to be attracted to unshared pairs on oxygen in water.
  3. 3,4-dimethylpentanal 2-ethylpentanal 2-chloroethanal 3-hydroxybutanal
  4. Propanone: This is a ketone, as indicated by the –one ending. There is only one carbon that is not an end carbon, so that is the only carbon that can have the carbonyl and the compound still be a ketone.Butanone: There are two non-end carbons on the four-carbon chain, but they are both equivalent. If we were to move the carbonyl to the other interior carbon, it might be tempting to number it 3-butanone, but that would be incorrect because numbering from the other end would take us back to having the carbonyl on the second carbon. Therefore, there is really only one position for the carbonyl and butanone needs no number.
  5. 1,1,1-trichloropropanone 3-chlorocyclopentanone
  6. Formalin is a solution of methanal (formaldehyde). Methanol is toxic and can cause blindness or death when as little as 4 mL is ingested. When we digest foods, they are “burned” to provide calories. This is actually the reaction of sugars produced from food with oxygen to produce carbon dioxide and water.When methanol is ingested and oxidized (burned), it forms formaldehyde and then formic acid before finally forming carbon dioxide. So, ingesting methanol causes your body to embalm itself, in a way!3,7-dimethyl-2,6-octadienal
  7. cinnamaldehyde 3-phenyl-2-propenal
  8. A tertiary alcohol has three alkyl groups attached to the carbinol carbon. Oxidation can only take place if the single carbon-oxygen bond in an alcohol can be replaced by a double carbon-oxygen bond; THIS can only take place if there is a hydrogen on the carbinol carbon to be lost when the oxygen forms an additional bond to the carbon. Since tertiary alcohols don’t have this hydrogen, they can’t be oxidized to carbonyl compounds.
  9. For the same reason tertiary alcohols can’t be oxidized, ketones can’t be oxidized. Oxidation required the formation of an additional C-O bond at the carbonyl group carbon. But this would require that the same carbon lose a hydrogen. There’s no hydrogen to lose, so there’s no oxidation.
  10. Oxidation products are2-methyl-2-propanone2-nonanonedecanal
  11. Products:1-chloro-2-propanol2-methyl-1-propanol
  12. Top row: hemiacetal, ketalBottom row: acetal, ketal