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triglycerides
            ur p  art 5
      nit fo g.j.rowlands
     u
                     ©anna_t@flickr
fats




                   can

©*Micky@flickr
                 taste...
©Mrs Magic@flickr
                   good!
provide
      more energy
than
     carbohydrate
         or protein




             ©swisscan@flickr
but...
is
   not
    very
good for s
        u




             ©Pixar / Disney
O

O
        O

    O

O

    O
            triglycerides
OH

      OH

 OH
glycerol




              triglyceride
           formation
OH
                     O
      OH   3x   HO                         R
 OH
glycerol                 fatty acid




                                         triglyceride
                                      formation
OH
                               O
      OH       3x         HO                            R
 OH
glycerol                              fatty acid


               O

           O                              R
                   O

               O                              R

           O                              R
                                                      triglyceride
               O       triglyceride                formation
natural
fats and oils




                ©Shereen M (away)@flickr
fatty acids




                           O

                      HO
                               myristic acid
©JustABigGeek@flickr
fatty acids




     O

HO


         oleic acid
fatty acids




                                  O

                             HO


©Chris & Lara Pawluk@flickr
                                      linolenic acid
saturated
 fat




       O

  HO



            ©Thomas Hawk@flickr
unsaturated
 fat




        O

   HO


              ©darwin bell@flickr
O

 HO




polyunsaturated
 fat              ©Marco Veringa@flickr
always
cis-alkenes

     O

HO
trans-fatty        are processed

acids




              O

 HO
©cultr.sun@flickr
saturated
chains




            CO2H
saturated
chains




            CO2H



                   pack well
high
melting points




©niznoz@flickr
                 solids
kinked
unsaturated
chains




              CO2H
kinked
unsaturated
chains




              CO2H



                     don’t
low
melting points




©☻mrhappy☻@flickr
                   oils
reactions




            ©euthman@flickr
O

      HO


addition
                 Br   Br
 reactions
         O                 Br
                                Br
    HO
O

HO


          H H
          metal
         catalyst
                    hydrogenation
     O               H
                         H
HO
O      unsaturated

HO


          H H
          metal
         catalyst
                         hydrogenation
     O                    H
                              H
HO

             saturated
of
synthesis
 margarine
     ©NontrivialMatt@flickr
ester
hydrolysis


     O            NaOH        O
             R2                          HO R2
R1       O               R1       O Na




                  saponification
ester hydrolysis
              O

          O
                  O

              O

          O

              O
                              NaOH
                               H2O
OH
              3x          O
     OH
              Na      O
OH
soap



         O

Na   O
how
does
  soap
 work?
O

Na   O



  polar        non-polar
hydrophilic   hydrophobic
micelle




   hydrophobic
     pocket
micelle     hydrophilic
          carboxylate
              interacts
               with water




               ion-dipole
          interactions
grease / dirt




    hydrophobic
non-polar
micelle
           hydrophobic
            portion inside
          away from water
detergents




    polar        non-polar
  hydrophilic   hydrophobic
    head            tail
synthesis of a
 detergent

                 H2SO4
                            electrophilic
                         aromatic substitution


     HO3S
                 NaOH




    Na   O3S
stronger
   acid




                    more
©fdecomite@flickr
                   robust
anionic
detergent


     O
         S
    O
             O
cationic
 detergent


  N

      Cl
cationic
  detergent


         N

              Cl

                   germicidal
©AJC1@flickr
fatty acid
metabolism
1             hydrolysis
              O

          O
                  O

              O

          O

              O
                              your
                              belly
OH
               3x         O
     OH
                      O
OH
2     metabolism
        O

    O

                     CoA-SH
                                  esterification
                  (coenzyme A)
            O
CoA
        S


                dehydrogenation        H    H
            O
CoA
        S
2     metabolism
          O
CoA
      S

                       hydration   H2O
          O       OH
CoA
      S
              H
                       oxidation         H   H

          O       O
CoA
      S
2     metabolism
          O       O
CoA
      S

                     CoA-SH            C–C
                  (coenzyme A)       splitting


                                     O
                          CoA
                                 S

              O
    CoA
          S
and
 repeat




©estherase@flickr
energy
from
     breaking
bonds



                  C H
©laverrue@flickr
O

HO



             more
               C–H
               than
         O

 HO
fat
 stores




                           2x
                       energy
                      of
©Great Beyond@flickr
                         sugar
thanks
  to
   Trevor Kitson

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Triglycerides