Embed Size (px)
Citation preview
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 1/56
©anna_t@flickr
trigl ycerides
g. j.ro wlandsun i t fo u r pa r
t 5
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 2/56
g jun
fa ts
can
tas te...©*Micky@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 3/56
good!©Mrs Magic@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 4/56
pr ov ide
more energ ythan car bohy dr ate
or pro tein
©swisscan@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 5/56
bu t...
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 6/56
is not
ver y
good f or
us
©Pixar / Disney
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 7/56 trigl ycerides
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 8/56
OH
OH
OH
glycerol
trigl yceride
formation
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 9/56
trigl yceride
formation
OH
OH
OH 3 xHO
O
R
glycerol fatty acid
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 10/56
trigl yceride
formation
OH
OH
OH 3 xHO
O
R
O
O
O
O
O
R
R
O
R
glycerol fatty acid
triglyceride
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 11/56
na tural
fatsand
oils
©Shereen M (away)@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 12/56
fa t t y acids
HO
O
myristic acid©JustABigGeek@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 13/56
HO
O
oleic acid
fa t t y acids
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 14/56
fa t t y acids
HO
O
linolenic acid©Chris & Lara Pawluk@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 15/56©Thomas Hawk@flickr
HO
O
sa tura ted
fat
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 16/56©darwin bell@flickr
unsa tura ted
fat
HO
O
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 17/56©Marco Veringa@flickr
HO
O
pol yunsa tura ted
fat
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 18/56
HO
O
al wa ys
c i s-alkenes
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 19/56
HO
O
©cultr.sun@flickr
acidst r a n s-f atty are processed
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 20/56
CO2H
sa tura ted
chains
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 21/56pack well
CO2H
sa tura ted
chains
h
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 22/56solids
high
melting points
©niznoz@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 23/56
unsa tura ted
chains
kinked
CO2H
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 24/56
CO2H
unsa tura ted
chains
kinked
don’t
l
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 25/56oils
lo w
melting points
©☻mrhappy☻@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 26/56
reac tions
©euthman@flickr
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 27/56
O
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 28/56
HO
O
H H
metalcatalyst
HO
O H
H
h ydrogena tion
O t t d
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 29/56
HO
O
H H
metalcatalyst
HO
O H
H
h ydrogena tion
sa tura ted
unsatur ated
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 30/56
t
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 31/56
R1
O
OR2
NaOH
R1
O
O Na
HO R2
hy dr oly sis
es ter
saponification
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 32/56
hydrolysiester
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 33/56
O
O
O
O
O
O
NaOH
H2O
OH
OH
OH
O
O
Na
3 x
hy dr oly sises ter
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 34/56
O
O
Na
soap
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 35/56
ho w
does
soap
wor k?
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 36/56
O
O
Na O
O
Na
polar
non-polar hy dr ophilic hydrophobic
i ll
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 37/56
micelle
hydrophobic
i ll h d hili
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 38/56
micellecar boxy late
hydrophilic
in terac tswith water
ion-dipole
in terac tions
/ di
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 39/56
gr ease / dir t
hydrophobic
i ll non-polar
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 40/56
micelle non-polar
hydrophobic
por tion inside
away from water
d t t
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 41/56
deter gents
polar
hy dr ophilic
head
non-polar
hydrophobic
tail
synth i of a
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 42/56
de tergen t
sy nthesis of a
H2SO4
HO3SNaOH
O3SNa
elec trophilic
aromatic substitution
stronger
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 43/56
acid
str onger
robust
mor e
©fdecomite@flickr
anionic
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 44/56
SO
O
O
O
de tergen t
anionic
cationic
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 45/56
N
Cl
N
de tergen t
cationic
cationic
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 46/56
©AJC1@flickr
de tergen t
cationic
N
Cl
germicidal
fatty acid
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 47/56
me tabolism
f atty acid
hydrolysis1
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 48/56
h ydrol ysis1
O
O
O
O
O
O
OH
OH
OHO
O3 x
yourbelly
metabolism2
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 49/56
me tabolism2
O
O
CoA-SH(coenzyme A)
esterification
S
O
CoA
dehydrogenation H H
S
O
CoA
metabolism2
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 50/56
me tabolism2
S
O
CoA
hydration H2O
S
O
CoA
H
OH
oxidation H H
S
O
CoA
O
metabolism2
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 51/56
me tabolism2
S
O
CoA
O
CoA-SH(coenzyme A)
C–Csplitting
S
O
CoA
O
SCoA
and
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 52/56
repea t
and
©estherase@flickr
energy
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 53/56
©laverrue@flickr
energ yf r om br eaking
bonds
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 54/56
HO
O
HO
O
more
C– H
than
fat
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 55/56
©Great Beyond@flickr
s tores
f at
energ y2 x
of
sugar
8/9/2019 Triglycerides - Organic Chemistry Notes at Examville.com
http://slidepdf.com/reader/full/triglycerides-organic-chemistry-notes-at-examvillecom 56/56
thanks to Trevor Kitson
